Vacation Rentals By Owner In Bayfield, WI

Steeple Hill Flats offers two modern hotel-style suites nestled into the Bayfield hillside overlooking downtown and the breathtaking Lake Superior, Apostle Islands, and the Madeline Island Ferry. The Upper Flat, located up a single flight of stairs on the second level, offers gorgeous views with a private balcony. Abundant in windows and natural light, this airy suite offer guests a chance to relax and rewind. Steeple Hill Flats is located in a quiet residential area, a short walk from the Madeline Island Ferry Line and everything downtown Bayfield has to offer. brbrThere is Queen bed and twin trundle beds around the corner down a hallway. Spalike amenities with large soaking tubs, luxurious robes, bath salts and Lake Superior views. Eating area offers a mini fridge with freezer, microwave, standard drip coffee maker, and a small table and chairs. Linens, towels and basic toiletries provided. Beach towels NOT included. There is a SmartTV and internet in the unit allowing accessibility to login to your own streaming channels, there is no cable. brbr*Comfortably sleeps 2-3 adults. brbr*No pets, no exceptions.*brProperty Name: Steeple Hill Flats-Upper FlatbrbrWELCOME!brThank you for choosing our cozy vacation property in beautiful Bayfield, Wisconsin — the gateway to the Apostle Islands! We’re thrilled you are here and we want your stay to be relaxing, enjoyable, and full of wonderful memories.brbrPlease treat this property like your own home (or like grandma is watching). These house rules could be summed up by simply saying: Take care of your friends and family. Clean up after yourself. Don’t break things. Be safe. Appreciate the amazing world around you.brbrUnfortunately, humanity has repeatedly proven that in order to keep everyone safe, protect the home for future guests, respect our neighbors, and ensure we stay in compliance with our governmental overlords (Wisconsin State Lodging Code (ATCP 72), Bayfield County Short-Term Rental Ordinance, and the local fire/municipal codes), we are legally required to put the following in writing.brbr1. Check-In & Check-OutbrCheck-in: After 4:00 PMbrCheck-out: By 10:00 AMbrA detailed welcome guide with codes, WiFi information, and helpful instructions will be available in your guest portal. If you’re arriving late, please let us know through the portal when you complete your online check-in form - we want to make sure you arrive and get into the unit without issue. brbrCheckout ProceduresbrbrThank you for helping us get the home ready for the next guests! Here’s what we ask:br- Leave by 10:00 AM so our cleaning team has enough time to prepare the property. If you need a late checkout please reach out the day before you checkout for approval - we will do our best to accommodate all requests. Late check-out fees may apply. br- Wash & sanitize any glassware you may have used. Supplies are under the bathroom sink. br- Take all trash and recycling to the designated canisters outside the front door of the building-near the garage. br- Check inside all drawers, check under the bed, check inside fridge, etc. to ensure you have all your belongingsbr- Turn off all lights.br- Leaves fans on low.br- COLD MONTHS: Sept/Oct through April: Set heat to 68 using thermostat. (Do not use minisplit/remote during the cold months). br- WARM MONTHS: May through Sept: Set air conditioning to 72 with remote. br- Close and lock all windows and doors - unit and exterior door touch bottom of the keypad to lock upon departurebrbrA quick final walk-through helps us a lot — we truly appreciate it!brbr2. Maximum Occupancy & Guestsbr- Maximum overnight guests: 4 (based on bedding and local ordinances).br- Day visitors are welcome but limited to no more than 2 at any time and must follow all house rules.br- No recreational vehicles, campers, tents, trailers, or additional lodging on the property.brbr3. Quiet Hours & Respect for Neighborsbr- Quiet hours: 10:00 PM – 8:00 AM daily (including weekends and holidays).br- Please keep noise to a respectful minimum at all times — no loud music, shouting, or gatherings that might disturb our neighbors.br- Fireworks are not permitted at any time.brbr4. Smoking & Vapingbr- This is a 100% smoke-free and vape-free property — inside and outside (including porches, decks, and yard).br- Violation will result in a minimum $300 deep-cleaning fee.brbr5. No Petsbr- No pets of any kind are allowed.br- If you have a service animal, please contact us in advance so we can make appropriate accommodations.brbr6. Parties & Gatheringsbr- No parties (including togas), events, weddings, receptions, or large gatherings.br- Small, quiet family gatherings are fine as long as they stay within occupancy limits and quiet hours.brbr7. Parkingbr- Spaces available for 1 vehicles in the guest parking area near the entrance to the building (1 spot for each unit)brbr8. Bikes, Motorized Items & EV ChargingbrNo bikes or motorized items (including e-bikes, scooters, motorcycles, etc.) are permitted inside the house or unit.br- EV Charging Policy: We do not have a dedicated EV charger on the property. Plugging electric vehicles into any household outlets is not permitted due to safety and insurance reasons. Public EV charging stations are available in downtown Bayfield (approximately 1 mile away).brbr9. ATVs, UTVs & Snowmobilesbr- These vehicles are not allowed at this property. We certainly welcome you to bring your toys, but there is not enough space in the parking area for trailers, etc. You are welcome to park on the side streets. Check local maps and ordinances for nearest trail access. brbr10. Trash, Recycling & Septic Systembr- Use the provided trash and recycling bins inside the unit during your stay.br- Please do not flush wipes, feminine products, diapers, paper towels, grease, or food scraps down the toilets or drains (our septic/sewer system thanks you!).br- At the end of your stay, please take all trash and recycling to the designated canisters outside near the stepsbrbr11. “Kitchennette”, Grill & Appliancesbr- Clean up after every usebr- Use appliances for their intended purpose.br- There is no grill or fire pit at this property. brbr13. General House Rulesbr- Please remove shoes at the door.br- Do not move furniture.br- Please do not bring linens or towels outside (especially to the beach.)br- Please don’t climb on roofs, railings, trees etc.br- Please don’t be the reason we need to make new rulesbrbr14. Safety & Emergenciesbr- Smoke detectors and carbon monoxide alarms are installed and functioning — please do not disable them. If they are chirping due to a low battery, please notify us immediately (no one wants to listen to this all night). br- A fire extinguisher is located in the hallway of the building. br- On the back of your room door. br- In case of emergency: Call 911 first, then contact us.br24/7 Emergency Contact:brWindseeker Rentalsbrbr15. Damage, Breakages & Cleaningbr- We know accidents happen, especially when we’re having fun. Please report any damage, spills, or issues to us immediately (before checkout). This allows us to properly prepare to fix issues before the next guest checks in)br- Please use appliances and amenities as they are intended. We are certain that you are intelligent enough to know that toaster ovens shouldn’t be used as stepstools and vacuum cleaners shouldn’t be used to split firewood. Please don’t prove us wrong. You are responsible for any damage beyond normal wear and tear. br- We include professional cleaning in your rate, but excessive mess may result in additional fees.brbrFinal NotebrBy booking and staying with us, you and your party agree to these house rules, the rental agreement, and all applicable local and state regulations.brWe truly appreciate you helping us keep this special place beautiful for everyone who visits. If you have any questions at all, please don’t hesitate to reach out!brWishing you a fantastic Bayfield adventure — enjoy the hiking, kayaking, orchards, and the stunning Apostle Islands!brWarmly,brWindseeker Rentals Team

Upper Flat @ Steeple Hill Flats, Bayfield

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$291.97

brThe Pilot House Admirals Quarters on first level downtown Bayfield with Lake Views! Located at the corner of 1st Street and Washington Avenue. Just 1 block from the Lake & Madeline Island Ferry. 1-3 blocks from beaches, and kayak rentals, with coffee shops, restaurants, boutiques, galleries, museums, marinas, and the library all within a short walk. The Iron Bridge Trail is just up the hill—no car needed. Best location for the Point to La Point swim in August. brbrPrivate Bath including jetted tub and separate shower, Roku 43 TV, WIFI, in room coffee, mini-refrigerator, King Bed & Queen Sofa-Sleeper, Sleeps 4 in 1 large bedroom, walk-in closet, table with 2 chairs, dresser, night stands, private door to outside East Lake View Deck. Lake Views, Walk to Everything! Overlooks Downtown Bayfield, Harbor, Madeline Island and Basswood Island. Common areas inside & out include (2) Large Lakeview Decks, Living Room, Octagon Lake View Living Room. Just 1 block from water and Ferry. Walk to everything in Bayfield. You are downtown next to the lake! Private parking just steps from main entrance. brbrBreakfast Blue Berry Muffins, yogurts, orange & grape juice. Coffee maker with coffee and condiments in room along with a Mini Refrigerator. Guests may use our Ice Machine in refrigerator and microwave. Paper plates, forks, knives, spoons, napkins, extra coffee, and condiments on table next to Refrigerator in Dining room. brbrAfter making a reservation, we will email you and you must immediately reply to our email (not VRBO messaging) with your full address, names of guests, there addresses and which are adults and children and their addresses, for Wisconsin Guest Registry Statute. Please reply to our email we will send you within 1 hour with this information. We will then email you door codes, arrival & departure instructions. brbrThank You!brJon Jack ArmstrongbrApostle RentalsbrBayfield, WI.

Bed & Breakfast

Bayfield Pilot House Admirals Quarters Lake Views. Sleeps 4 in same room.

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$250.86

You'll love this fully renovated studio condo that is literally steps from the beach! This unit is bright & airy with modern decor and all the thoughtful touches that make this the perfect place to serve as home base for your escape to Bayfield. The unit may be compact, but it is fully featured and oh-so-charming! You'll enjoy a full kitchen, dining area, comfy couch and side chair, queen-size bed, and a beautiful full bathroom. Not to mention your own patio overlooking the lake and the beach!brbrYour Host:brYour host runs Bark Point Ventures, a vacation rental management & concierge company that specializes in properties all along Lake Superior's South Shore. We live nearby and are available whenever needed to assist our guests. Our passion is ensuring guests experience the magic of what we feel is one of the most amazing places in the world.brbrLocation:brLocated on the beach right in downtown Bayfield. You can walk to a wide range of locally-owned shops, restaurants, galleries, and museums. And yet the condo is set far enough away from the main drag to not feel like you're too in the middle of everything. brbrAccess:brOne parking space per unit is provided in the parking lot. Street parking is also readily available except during the fall Applefest celebration. brbrBayfield is a very walkable city, so your best bet is on foot. We are just a couple blocks from all the shops and restaurants in downtown Bayfield.brbrThe following shuttles and ferries are also accessible on foot from Reiten Boatyard:brbr - The Madeline Island Ferry will take you out to Madeline Island and runs regularly during the late spring, summer, fall, and much of the winter. brbr- The BART Bus runs regularly from through Bayfield and around Chequamegon Bay for a modest fee.brbr- Big Top Chautauqua runs shuttles for most of for their concerts and events.brbrThe space:brThis newly renovated studio unit is located on the ground floor, literally steps from the beach & the lake. The unit features a very comfy queen-size Murphy bed (let the sound of the waves lull you to sleep!), sofa, dining table & chairs, fully-equipped kitchen, full bath, and a private patio for dining al fresco with views of the lake! Non working fireplace. Ornamental only. Everything has been recently renovated and full of artful touches and modern conveniences. brbrThe unit also features a rarity in the area: air conditioning, as well as high-speed wifi. brbrLocation + Transit:brDue to the lack of public transportation and the distance between towns/amenities, a car is pretty much essential. But, on the plus side, traffic is not a concept we have up here!brbrWalk to downtown shops and restaurants, ferry terminal and recreation center. brOff street parking in lot for one car. Plenty of street parking available, except during Applefest weekend in October. Less than 15 minute drive to Mt. Ashwabay ski hill, Big Top Chautauqua, hiking trails, beaches, and more.brbrPublic transportation on the peninsula is provided by the Bay Area Rural Transit (BART), more information can be found on their website.brbrAn EV charging station is located in the parking lot on the corner of Washington Ave. and E. 6th St. in Washburn.brbrBe aware that sound and vibration travel easily in this building. Please be considerate of your neighbors and keep voices and TV levels down and please walk softly on stairway as well as inside the condo. brNon working fireplace- ornamental only.brThere are 2 picnic tables and 2 weber grills available for use by guests and residents of all units. brBike racks are also available by the parking lot.brSmoking of any kind, including e-cigs, is strictly prohibited either in or outside the condos or anywhere on the premises.brAs much as we love dogs, canine guests are NOT allowed at this property. We're happy to help you locate a dog-friendly rental should you require one.

Bayfield Studio | Lake Superior Views

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$1281.39

MORE updates and photos coming Spring 2026! Escape to this stunning log cabin on Lake Superior, just outside Bayfield, Wisconsin, and minutes from the Apostle Islands. Surrounded by forest and water views, this spacious retreat is perfect for large groups, family gatherings, and unforgettable Northwoods getaways.brbrInside, soaring vaulted ceilings, exposed log beams, and a dramatic stone fireplace anchor a bright, open great room. The fully equipped kitchen, featuring a large island and bar seating, is ideal for cooking and gathering, while multiple living spaces provide ample room for everyone to relax.brbrWith comfortable sleeping accommodations for up to 18 guests, there’s plenty of space to spread out while still enjoying time together. Beds include: one King beds, three Queen beds, two Twin beds, one Queen futon, and 2 Twin/Full bunk beds. All linens and towels included. brbrStep outside to take in peaceful lake views, enjoy the deck, and experience the beauty of Lake Superior in every season. A warm, inviting retreat in one of Wisconsin’s most iconic destinations—perfect for making lasting memories near Bayfield and the Apostle Islands.

Lake Superior Log Cabin Retreat | Near Bayfield, WI | Sleeps 18

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$258.98

brThe Pilot House (WIFI) Crew's Quarters in the Lower Level of The Pilot House B & B in downtown Bayfield, 14 Steps down. Lake Views! Just 1 block from the Lake & Madeline Island Ferry. 1-3 blocks from beaches, and kayak rentals, with coffee shops, restaurants, boutiques, galleries, museums, marinas, and the library all within a short walk. The Iron Bridge Trail is just up the hill—no car needed. Lake Views. Common areas with 2 Lake View decks! Best location for Lake & Downtown Views as well as the Point to La Point swim in August. brbrSteep driveway, enter slowly at an angle. AC, 32 Flat Screen Roku TV, Mini Frig, private bathroom with shower. The Pilot House Crew's Quarters is 14 steps down to the lower level. Several windows on the East, & South sides of the Crew's Quarters provide partial lake views at lawn level. Common areas including on he first level have 2 large decks on East & South sides (Both decks have Lake & Town Views) The Octagon Lake View Room and front room. Just up the stairs on the 1st level, (both have lake & harbor views) with tables and chairs, large living room rectangular and octagon in shape with all windows facing the lake. brbrBreakfast Blue Berry Muffins, yogurts, orange & grape juice. Coffee maker with coffee and condiments in room along with a Mini Refrigerator. Guests may use our Ice Machine in refrigerator and microwave. Paper plates, forks, knives, spoons, napkins, extra coffee, and condiments on table next to Refrigerator in Dining room. brbrAfter making a reservation, we will email you and you must immediately reply to our email (not VRBO messaging) with your full address, names of guests, there addresses and which are adults and children and their addresses, for Wisconsin Guest Registry Statute. Please reply to our email we will send you within 1 hour with this information. After we receive, we will email you a door code, arrival & departure instructions. brbrThank You!brJack ArmstrongbrApostle RentalsbrBayfield, WI.

Bed & Breakfast

Bayfield Pilot House Crew's Quarters Sleeps 2. Lake Views. 1 block from Ferry.

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$370.17

brWelcome to Ada O’Day Condominium #2, a spacious and charming second-floor condo offering beautiful views of Lake Superior and an unbeatable Bayfield location. Just one block up from Rittenhouse Avenue—Bayfield’s quaint main street—you’re steps from shops, restaurants, the ferry, and more.brbrThis two-bedroom, two-bathroom unit comfortably accommodates up to four guests. Each bedroom features a queen bed, making it perfect for couples, friends, or a small family getaway. With approximately 1,300 square feet, the open and airy floor plan includes a cozy living room with a gas fireplace, a dedicated dining area, and a separate TV room for quiet relaxation.brbrThe fully equipped kitchen has everything you need to prepare meals, while the covered outdoor porch provides a lovely spot to enjoy your morning coffee and take in Lake Superior views. On-site laundry adds extra convenience for longer stays.brbrThe building was completely renovated in 2005, thoughtfully preserving its original charm while offering modern comforts. There are steps leading into the condo from both entrances, but once inside, the unit is all on one level.brbrHighlights:br* 2 bedrooms with queen bedsbr* 2 full bathrooms (one with a tile shower in the primary bedroom, 2nd one in central hallway has a bathtub/shower combination)br* Sleeps up to 4 guestsbr* Lake Superior views from the covered porchbr* Fully equipped kitchen & gas fireplacebr* Separate TV roombr* On-site laundrybr* One parking space (plus street parking)br* Walk to shops, dining, and ferrybrbrPark your car, settle in, and enjoy everything Bayfield has to offer—right outside your door.brbrThis condo was previously managed by The Bayfield Inn. As of 4/1/26, the unit is now individually owned and managed. brbrAccessibility: When entering the condo from the street level, you will need to walk down 8 steps to enter the front door. To enter from the alley were the parking lot is, you will need to walk up a total of 14 stairs to enter the back door. Once you enter the condo, it is all one level.

Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$1044.33

This historic Victorian home has a long history of welcoming guests to beautiful Bayfield, WI. Perched on a hill overlooking Lake Superior and the Bayfield Ferry Dock, you can watch the sun rise over the Lake from our location, as well as the daily ferry crossings to Madeline Island. brbrDecorated in a modern Victorian style, this home is spacious enough for a family gathering, or a weekend getaway for several couples. Three spacious bedrooms on the second level, and a bright and airy attic with high ceilings are idyllic and cozy spaces to retire for the night. brbrLarge windows throughout the house flood each room with warm light, and a formal dining room with a magnificent stained-glass chandelier is the perfect spot to share a meal together. The Harbor Hill House kitchen is fully stocked with dishes and meal prep items, for the nights you feel like eating in.brbrAmenities include Wi-Fi, A whirlpool tub, and close proximity to downtown area shops, restaurants and Lake Superior activities.brbrOur guests love to hang out on the wraparound porch where they can view the sailboats flitting over lake Superior during the day, and to see the twinkling city lights at night.brThis historic Victorian home has a long history of welcoming guests to beautiful Bayfield, WI. Perched on a hill overlooking Lake Superior and the Bayfield Ferry Dock, you can watch the sun rise over the Lake from our location, as well as the daily ferry crossings to Madeline Island. brbrDecorated in a modern Victorian style, this home is spacious enough for a family gathering, or a weekend getaway for several couples. Three spacious bedrooms on the second level, and a bright and airy attic with high ceilings are idyllic and cozy spaces to retire for the night. Several Roll Away beds are available for extra guest space.brbrLarge windows throughout the house flood each room with warm light, and a formal dining room with a magnificent stained-glass chandelier is the perfect spot to share a meal together. The Harbor Hill House kitchen is fully stocked with dishes and meal prep items, for the nights you feel like eating in.brbrOur guests love to hang out on the wraparound porch where they can view the sailboats flitting over lake Superior during the day, and to see the twinkling city lights at night.brbrBEDROOM LAYOUTbrbrSecond Level 1 King, 2 QueensbrbrThird Level 2 QueensbrbrSERVICE ANIMALS - SERVICE ANIMALS - Please note, we only accept pets on a case by case basis and a 150 dollars pet fee will apply in addition to your nightly rate. If you want to bring your pet, or if your pet is a service animal, please notify us prior to booking as pet stays require additional cleaning.

Harbor Hill House Bayfield, WI

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$209.44

If you love the peace and serenity of the woods but still appreciate having convenient access to town, then Woodland Lodging is the place to be! This charming & clean upstairs apartment is nestled up in the woods on a quiet dead-end road just short a 5-minute drive to downtown Bayfield. Head down the hill into Bayfield for dining, shopping, beaches, and hiking. If golfing is your thing, just a 3-minute drive up the hill and you’ll find the gorgeous Apostle Highland Golf Course. brbrYour host runs Bark Point Ventures, a vacation rental management & concierge company that specializes in properties all along Lake Superior's South Shore. We live nearby and are available whenever needed to assist our guests. Our passion is ensuring guests experience the magic of what we feel is one of the most amazing places in the world.br As much as we love dogs, canine guests are NOT allowed at this property. We're happy to help you locate a dog-friendly rental should you require one.brbrNeighborhoodbrWoodland Lodging complex is located on a peaceful wooded lot, just a 5 minute drive to Bayfield's commercial district with a wide range of shops, restaurants, galleries, beaches and the ferry landing. The home sits on a quiet dead-end road and offers a peaceful escape with the convenience of being close to town. brbrSpacebrIf you love the peace and serenity of the woods but still appreciate having convenient access to town, then Woodland Lodging is the place to be! This charming property is nestled up in the woods on a quiet dead-end road just short a 5-minute drive to downtown Bayfield. Head down the hill into Bayfield for dining, shopping, beaches, and hiking . If golfing is your thing, just a 3-minute drive up the hill and you’ll find the gorgeous Apostle Highland Golf Course. brbrThis upper unit of the property features an open plan living/dining/kitchen area with a comfy couch, 2 chairs, a dining table with seating for four, a fully-outfitted kitchen, and high-speed wifi that makes streaming your favorite content on the smart tv (Roku) or your preferred device a breeze. The primary bedroom has a queen bed and the living room has a newer full-sized futon. The full bath has a combo tub/shower. The apartment is set up perfectly for 2 but can comfortably accommodate 2 additional small children or single adult on the futon in the living room. brIn the summer months there is an herb garden right off the front deck that guests are welcome to pick from. brbrTransitbrDue to the lack of public transportation and the distance between towns/amenities, a car is pretty much essential. But, on the plus side, traffic is not a concept we have up here!brbrCabin & Property Amenitiesbr-This unit is the upstairs unit of the Woodland Lodging building.br-1 bedroom with a king sized bed, a full-sized futon in the living room, and a full kitchen & bath.br- Dining seating for 4 br- High-speed wifi & smart TVbr-Sweet front porch from which to enjoy your morning coffee or evening cocktails from.br- Perfect location for exploring everything Bayfield has to offer!br As much as we love dogs, canine guests are NOT allowed at this property. We're happy to help you locate a dog-friendly rental should you require one.

Woodland Lodging | 5 minutes to Downtown Bayfield

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$701.1

Our 4 bedroom, 2 bathroom (1,800 sq. ft) cottage home is a wonderful place to call home while visiting the Apostle Islands National Lakeshore and the Bayfield, WI area. We are located in the historic district of Bayfield and a 5 - 6 minute walk (hills included) to the downtown area which hosts many quaint shops, restaurants, grocery store, city park with gazebo, city marina, and a 20 minute ferry service to the pearls of Madeline Island. The Big Top Chautauqua, a summer must for lively entertainment, is only 2 miles south of town. Blueberry, strawberry, apple and raspberry picking, a favorite family activity from local farms, is only minutes away (during appropriate seasons). We can host up to 8 people. br brOur first level of the home features a bedroom with a double bed, full bath with shower/tub combo immediately across the hall, living room, kitchen, dining room, laundry room and a large exterior deck.brbrOn the second level you will find a Master bedroom with a queen bed, 3rd bedroom with 2 twin beds, a 4th bedroom with a full size bed along with a shared bathroom with a walk-in shower.brbrOur large deck is the perfect place to enjoy our flower gardens and a cup of coffee before heading out to explore what the Bayfield area has to offer. Sit down for dinner on the deck where friends and family can build wonderful memories to take home. brbrWalk out our front door and across the street to the iconic, brownstone building which hosts the Apostle Islands National Lakeshore Headquarters. The center offers orientation and information, camping permits, museum exhibits, a park film and the America’s National Parks bookstore.brbrWhile staying at the Gichi Gami House, you are in the land of the Red Cliff Band of Lake Superior Chippewa, the hub of the Chippewa nation. The Red Cliff Reservation is conveniently located 2 miles north of Bayfield on Hwy 2. There, you’ll find Legendary Waters Resort & Casino and the Copper Crow Distillery, the only native run distillery in the country. Share stories with others over a shot of gin or vodka. On Madeline Island in the town of La Pointe, an easy 20 minute ferry ride from Bayfield, is the Madeline Island Museum which features artifacts of local native tribes, relics of French fur traders dating back to 1693, and early missionaries who with local natives established the fur post. People of the Chippewa nation refer to the lake as Gichi Gami, the “Great Sea”.brbrSome of the amenities you will find at our home include: Gas fireplace in living room, grill, Smart TV (bring your login credentials for Netflix, Prime, Hulu, etc), internet, WiFi, washer/dryer, dishwasher, microwave, heating, air conditioning, towels, linens and two parking spaces in front of the garage (more street parking available in front of the home).brbrPlease note that there are 3 steps to enter the front entry and approximately 6 to enter onto the deck from the back. Note, access to the upstairs bedrooms is from a 16 step staircase. brAll guests will be required to sign a Short Term Rental agreement once they have booked our home.brbrThe house and outdoor spaces are yours to enjoy. Please note that the garage is off limits. Only registered guests are allowed in the home and on the property. brbrSecurity Cameras:brSimilar to other vacation rental homes, we have Ring doorbell cameras located at the front door and back door of the home. As you would expect, the audio recording has been turned off.brbrMilitary Personnel Discount:brWe offer a 10% discount on the nightly rate (not including fees and taxes) for active, retired, and reserve military personnel. Please contact us prior to reservation and present your current military ID or DD214 for the discount.brbr7 night minimum rental per city of Bayfield short term rental ordinance

Entire Home located in historical district

Bayfield, Wisconsin, United States

4

Bed

Bath

8

Sleeps

$389.1

NEWLY UPDATED 2026!brbrThis cozy one-bedroom condominium in the heart of Downtown Bayfield is getting a fresh facelift, with updated photos coming soon. Perfectly located just steps from shopping, dining, the waterfront, and the Madeline Island ferry, this unit offers both comfort and convenience for your Bayfield getaway.brbrThe open-concept living, dining, and kitchen area is warm and welcoming, featuring hardwood floors, comfortable furnishings, and plenty of natural light. The living room includes a sleeper sofa, providing additional sleeping space, and is ideal for relaxing after a day of exploring. Enjoy meals together at the dining table or unwind with a movie in the evening. The kitchen is well-equipped for preparing everything from quick breakfasts to full dinners.brbrStep outside to your private exterior deck, where you can take in views of Lake Superior and Memorial Park—perfect for morning coffee, afternoon reading, or watching the sunrise. The King bedroom offers a peaceful retreat, and thoughtful touches throughout the unit make your stay easy and relaxing.brbrWhether you’re visiting for a weekend escape or a longer stay, this downtown condo is an ideal home base while enjoying all that Bayfield has to offer. Check back soon for updated photos showcasing the latest improvements.brbrAll linens, towels and toiletries provided. (Beach towels not included). $25/guest/night after 2.brProperty Name: #200-Historic Tate Building brAddress: 10 1st. Street #200 Bayfield, WI 54814brbrWELCOME!brThank you for choosing our cozy vacation property in beautiful Bayfield, Wisconsin — the gateway to the Apostle Islands! We’re thrilled you are here and we want your stay to be relaxing, enjoyable, and full of wonderful memories.brPlease treat this property like your own home (or like grandma is watching). These house rules could be summed up by simply saying: Take care of your friends and family. Clean up after yourself. Don’t break things. Be safe. Appreciate the amazing world around you.brbrUnfortunately, humanity has repeatedly proven that in order to keep everyone safe, protect the home for future guests, respect our neighbors, and ensure we stay in compliance with our governmental overlords (Wisconsin State Lodging Code (ATCP 72), Bayfield County Short-Term Rental Ordinance, and the local fire/municipal codes), we are legally required to put the following in writing:brbr1. Check-In & Check-OutbrCheck-in: After 4:00 PMbrCheck-out: By 10:00 AMbrbrA detailed welcome guide with codes, WiFi information, and helpful instructions will be available in your guest portal. If you’re arriving late, please let us know through the portal when you complete your online check-in form - we want to make sure you arrive and get into the unit without issue. brbrCheckout ProceduresbrThank you for helping us get the home ready for the next guests! Here’s what we ask:br- Leave by 10:00 AM so our cleaning team has enough time to prepare the property. If you need a late checkout please reach out the day before you checkout for approval - we will do our best to accommodate all requests. Late check-out fees may apply. br- Start the dishwasher before departure. br- Take all trash and recycling to the onsite dumpster (recycling should all be free / loose and cardboard broken down - pizza boxes do not go in recycling)br- Check inside all drawers, check under the bed, check inside fridge, etc. to ensure you have all your belongingsbr- Unplug any counter appliances (i.e. coffee maker, toaster, etc.)br- Turn off all lightsbr- Leave fans on lowbr- COLD Season: Sept/Oct through April: Set heat to 65. br- WARM Season: May through Sept: Set air conditioning to 72. br- Close and lock all windows and doors. Front door - touch bottom of the keypad to lock upon departurebrbrA quick final walk-through helps us a lot — we truly appreciate it!brbr2. Maximum Occupancy & GuestsbrMaximum overnight guests: 4 (based on bedding and local ordinances).brDay visitors are welcome but limited to no more than 2 at any time and must follow all house rules.brNo recreational vehicles, campers, tents, trailers, or additional lodging on the property.brbr3. Quiet Hours & Respect for NeighborsbrQuiet hours: 10:00 PM – 8:00 AM daily (including weekends and holidays).brPlease keep noise to a respectful minimum at all times — no loud music, shouting, or gatherings that might disturb our neighbors.brFireworks are not permitted at any time.brbr4. Smoking & VapingbrThis is a 100% smoke-free and vape-free property — inside and outside (including porches, decks, and yard).brViolation will result in a minimum $300 deep-cleaning fee.brbr5. No PetsbrNo pets of any kind are allowed - this unit is in a condo association with multiple unitsbrIf you have a service animal, please contact us in advance so we can make appropriate accommodations.brbr6. Parties & GatheringsbrNo parties(including togas), events, weddings, receptions, or large gatherings.brSmall, quiet family gatherings are fine as long as they stay within occupancy limits and quiet hours.brbr7. ParkingbrParking is available for up to 1 vehicle in the shared parking lot. Please use the designated parking pass in your car and return to the unit before departurebrLimited street parking is also available, please be mindful of timed parking or snow removal routes with the City of Bayfieldbrbr8. Bikes, Motorized Items & EV ChargingbrNo bikes or motorized items (including e-bikes, scooters, motorcycles, etc.) are permitted inside the condo or the building. brEV Charging Policy: We do not have a dedicated EV charger on the property. Plugging electric vehicles into any household outlets is not permitted due to safety and insurance reasons. Public EV charging stations are available across the street. brbr9. ATVs, UTVs & SnowmobilesbrThese vehicles are not allowed at this property. We certainly welcome these vehicles, but the parking lot would not accommodate trailers and most of the side streets around need to be clear from 2am to 6am. brbr10. Trash, Recycling & Septic SystembrUse the provided trash bins inside the unit during your stay.brPlease do not flush wipes, feminine products, diapers, paper towels, grease, or food scraps down the toilets or drains (our septic/sewer system thanks you!).brAt the end of your stay, please take all trash to the onsite dumpster.brbr11. Kitchen, Grill & Appliances.brClean up after every use.brUse appliances for their intended purpose.brGrills are not permitted at this property. brbr12. Fireplaces & Fire PitbrThe gas fireplace in the unit is controlled by the thermostat. Please make sure you set it back to the above listed temperature when departing. brThere is no firepit at this property. brbr13. General House RulesbrPlease remove shoes at the door.brDo not move furniture.brPlease do not bring linens or towels outside (especially to the beach.)brPlease don’t climb on roofs, railings, trees etc.brPlease don’t be the reason we need to make new rulesbrbr14. Safety & EmergenciesbrSmoke detectors and carbon monoxide alarms are installed and functioning — please do not disable them. If they are chirping due to a low battery, please notify us immediately (no one wants to listen to this all night). brA fire extinguisher is located in the front entry closet.brAn evacuation map is posted on the front door in the unit. brbrIn case of emergency: Call 911 first, then contact us.brbr15. Damage, Breakages & CleaningbrWe know accidents happen, especially when we’re having fun. Please report any damage, spills, or issues to us immediately (before checkout). This allows us to properly prepare to fix issues before the next guest checks in. brPlease use appliances and amenities as they are intended. We are certain that you are intelligent enough to know that toaster ovens shouldn’t be used as stepstools and vacuum cleaners shouldn’t be used to split firewood. Please don’t prove us wrong. You are responsible for any damage beyond normal wear and tear. brWe include professional cleaning in your rate, but excessive mess may result in additional fees.brbrFinal NotebrBy booking and staying with us, you and your party agree to these house rules, the rental agreement, and all applicable local and state regulations.brbrWe truly appreciate you helping us keep this special place beautiful for everyone who visits. If you have any questions at all, please don’t hesitate to reach out!brWishing you a fantastic Bayfield adventure — enjoy the hiking, kayaking, orchards, and the stunning Apostle Islands!brbrWarmly,brWindseeker Rentals Team

Downtown Lodging in Historic Building

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$255.41

Newly updated unit! Welcome to Brookside Hide-A-Way at the Port Superior Marina! This one-bedroom, one-bathroom apartment is situated just 2 miles from Bayfield and offers convenient access to the Brownstone walking/biking trail, located alongside Lake Superior. This comfortable space sleeps 2-4, featuring a king bed, private bathroom, queen sleeper sofa, full kitchen, smart TV, and high-speed Wi-Fi. You are just a one-minute walk to two full-service marinas, the Portside Bar and Restaurant, a shared outdoor fire pit, and more walking trails nearby. This condo is a main-level unit, walk-in with two small stairs. brbrSleeps 4. Extra guest fee ($25/night per person) after 2 people.brbr**Pets are not permitted at this property, NO exceptions**

Brookside Hide-A-Way #2, Port Superior, Bayfield

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$1177.2

- Family Friendly Vacation Rental by Owners w/ Glowing Reviews!br-Prime location in Bayfield, very near to the Marina and Ferry to Madeline Island. br-4 BR & 3.5 BA; 3 bedrooms have en-suite. br-Right across from the historic Rittenhousebr-Walkable to Park, downtown Bayfield shops, restaurantsbr-Whole basement for getting together with a pool table, giant connect 4 and a large smart TV.br-Spacious and comfortable 4-bedroom, 3.5-bath home – perfect for families or groupsbr-Two living areas for relaxing, socializing, or spreading outbr-Stunning Lake Superior views from the upstairs living room and primary bedroombr-Fully equipped kitchen with everything you need for dining inbr-Wi-Fi, TV, and other modern comfortsbrbrbrWelcome to your Bayfield Lakeview Getaway, a spacious and light-filled home just three blocks from the Bayfield Marina and Madeline Island Ferry. Located directly across from the iconic Rittenhouse Inn, this home offers a rare combination of convenience, comfort, and scenic beauty—all within easy walking distance to downtown Bayfield’s shops, restaurants, and lakefront activities.brbrThis two-level, 4-bedroom, 3.5-bath home is perfect for families, couples traveling together, or small groups looking to relax in a peaceful setting with plenty of room to spread out.brbrMain Floor Features:br-Two well-appointed bedrooms, each with a private en suite full bathroombr-Open-concept living space with comfortable seating and large windows that frame beautiful greenery and Lake Superior viewsbr-Fully equipped kitchen ideal for cooking meals at homebr-Dining area with ample seating for your groupbr-Easy entry with just six steps leading up to the front porchbr-Lockbox check-in for convenient and secure accessbrbrUpstairs:brbr-Two large bedrooms with plenty of space and storagebr-The primary upstairs bedroom includes a private half bath and sweeping views of Lake Superiorbr-A spacious full bathroom on the upper level for added conveniencebr-A second cozy living space—great for reading, games, or quiet conversationbrbrbrAdditional Highlights:br-Abundant natural light throughout the home with large windows and views of the surrounding trees and lakebr-Two living rooms, one on each level, offering plenty of seating and room for everyone to relaxbr-One off-street parking space and more street parking. br-Wi-Fi, smart TV, and all the essentials for a comfortable staybr-Ideal location for Twin Cities visitors, just a few hours’ drive from Minneapolis–St. PaulbrbrWhether you’re here for a summer getaway, a fall color tour, or apple fest, this Bayfield home offers a welcoming and comfortable basecamp in one of Wisconsin’s most charming lakeside towns.

Downtown Bayfield Home W/ Lake Views, Near Ferry & Marina

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$947.54

Enjoy Lake Superior views for days from this beautifully appointed home just south of downtown Bayfield, complete with expansive wraparound deck. The main level features a full kitchen that overlooks a formal dining room and a sprawling living room. Second level features a king lakeside bedroom, full bedroom, full bathroom, office/den and a twin trundle bedroom. Third level for a lofted style king suite overlooking the lake and its own en suite bathroom with shower. brbrDue to safety concerns, indoor fireplace is off limits. Guests are permitted to have outdoor campfire, but must provide their own firewood and adhere to local fire laws and bans and make sure fires are fully extinguished. brbr*NO pets permitted, no exceptions*brParking is available in front of the garage. Please do not block the neighbor`s driveway and access to their property.

Lakeshore Retreat on Lake Superior, Bayfield

Bayfield, Wisconsin, United States

4

Bed

Bath

8

Sleeps

$885.22

Welcome to your perfect Bayfield getaway! This charming home in the heart of downtown Bayfield, Wisconsin, offers comfort, style, and unbeatable convenience just steps from local shops, dining, and the Lake Superior waterfront.brbrThe property features 2 bedrooms, 3 bathrooms, and fully stocked kitchens, providing everything you need for a relaxing stay. With space to sleep up to 10 guests, it’s ideal for families, groups, or extended weekend escapes. Both sides of the home are thoughtfully furnished with a warm coastal feel, filled with natural light, inviting living spaces, and relaxing amenities. Unwind in the soaking tub with views of Lake Superior after a day exploring the Apostle Islands.brbrMain Unit: King ensuite upstairs, Queen murphy bed and Full pullout sofa bed in the dining/living room. brCarriage Unit: Queen bed and Full futon sleeper. brbrAll towels and linens included. Sleeps up to 10. $25 / night / person after 6.brProperty Name: Hendrickson House (Entire Unit)brbrWELCOME!brThank you for choosing our cozy vacation property in beautiful Bayfield, Wisconsin — the gateway to the Apostle Islands! We’re thrilled you are here and we want your stay to be relaxing, enjoyable, and full of wonderful memories.brPlease treat this property like your own home (or like grandma is watching). These house rules could be summed up by simply saying: Take care of your friends and family. Clean up after yourself. Don’t break things. Be safe. Appreciate the amazing world around you.brbrUnfortunately, humanity has repeatedly proven that in order to keep everyone safe, protect the home for future guests, respect our neighbors, and ensure we stay in compliance with our governmental overlords (Wisconsin State Lodging Code (ATCP 72), Bayfield County Short-Term Rental Ordinance, and the local fire/municipal codes), we are legally required to put the following in writing.brbr1. Check-In & Check-OutbrCheck-in: After 4:00 PMbrCheck-out: By 10:00 AMbrbrA detailed welcome guide with codes, WiFi information, and helpful instructions will be available in your guest portal. If you’re arriving late, please let us know through the portal when you complete your online check-in form - we want to make sure you arrive and get into the unit without issue. brbrCheckout ProceduresbrThank you for helping us get the home ready for the next guests! Here’s what we ask:br- Leave by 10:00 AM so our cleaning team has enough time to prepare the property. - If you need a late checkout please reach out the day before you checkout for approval - we will do our best to accommodate all requests. Late check-out fees may apply. br- Wash any used dishes. Run dishwashers upon checkout. br- Please tie up all trash and set it together for housekeeping to remove after departure. br- Check inside all drawers, check under the bed, check inside fridge, etc. to ensure you have all your belongingsbr- Unplug any counter appliances (i.e. coffee maker, toaster, etc.)br- Turn off all lightsbr- Leaves fans on lowbr- COLD MONTHS: Sept/Oct through April: Set Heat to 68 upon departure.br- WARM MONTHS: May through Sept: Set AC to 72br- Close and lock all windows and doors (especially the back door) - front door touch bottom of the keypad to lock upon departurebrbrA quick final walk-through helps us a lot — we truly appreciate it!brbr2. Maximum Occupancy & Guestsbr- Maximum overnight guests: 10 (based on bedding and local ordinances).br- If needed, pillows and blanket for the Murphy Bed are located in the white tote bags located in the laundry closet behind the couch. The key to unlock the bed is in that closet as well. Please read the instructions ON the bed prior to using. br- If needed, pillows and linens for the pullout couch are located in the white tote bag in the ottoman at the end of the couch. br- If needed, pillows, mattress protector and linens for the futon in the Carriage unit are in the bench seat/chestbr- If you use the Murphy bed, the pullout couch or futon, please leave the linens out (do not put away) - so we know they were used and these need to be watched. br- Day visitors are welcome but limited to no more than 4 at any time and must follow all house rules.br- No recreational vehicles, campers, tents, trailers, or additional lodging on the property.brbr3. Quiet Hours & Respect for Neighborsbr- Quiet hours: 10:00 PM – 8:00 AM daily (including weekends and holidays).br- Please keep noise to a respectful minimum at all times — no loud music, shouting, or gatherings that might disturb our neighbors.br- Fireworks are not permitted at any time.brbr4. Smoking & Vapingbr- This is a 100% smoke-free and vape-free property — inside and outside (including porches, decks, and yard).br- Violation will result in a minimum $300 deep-cleaning fee.brbr5. No Petsbr- No pets of any kind are allowed.br- If you have a service animal, please contact us in advance so we can make appropriate accommodations.brbr6. Parties & Gatheringsbr- No parties(including togas), events, weddings, receptions, or large gatherings.br- Small, quiet family gatherings are fine as long as they stay within occupancy limits and quiet hours.brbr7. Parkingbr- Parking is available for up to 2 vehicles in the Carriage House driveway. br- Please do not block the driveway or neighbors’ access.br- No parking on the grass or lawn.br- Limited street parking is also available. brbr8. Bikes, Motorized Items & EV Chargingbr- No bikes or motorized items (including e-bikes, scooters, motorcycles, etc.) are permitted inside the house or unit.br- EV Charging Policy: We do not have a dedicated EV charger on the property. Plugging electric vehicles into any household outlets is not permitted due to safety and insurance reasons. Public EV charging stations are available in downtown Bayfield (less than 1 mile away).brbr9. ATVs, UTVs & Snowmobilesbr- These vehicles are not allowed to be used onsite at this property. We welcome you to bring these and enjoy the local trails, but will require travel to the trail heads. brbr10. Trash, Recycling & Septic Systembr- Use the provided trash bins inside the unit during your stay. If you are here for an extended stay and need additional trash removal, please notify us. br- Please do not flush wipes, feminine products, diapers, paper towels, grease, or food scraps down the toilets or drains (our septic/sewer system thanks you!).br- At the end of your stay, please tie up all trash and set it together for housekeeping to remove after departure. brbr11. Kitchen, Grill & Appliancesbr- Clean up after every usebr- Use appliances for their intended purpose.br- Private cookware is not permitted on decks or within 10 ft of structures. Please see grill for additional instructions for use. brbr12. Fireplaces & Fire Pitbr- Feel free to enjoy the gas fireplace in the main unit inside during cooler months — just remember to turn it off when you’re done. (the pilot light should still remain on, even when the unit is off)br- There is not an outdoor firepit at this unit. brbr13. General House Rulesbr- Please remove shoes at the door.br- Do not move furniture.br- Please do not bring linens or towels outside (especially to the beach.)br- Please don’t climb on roofs, railings, trees etc.br- Please don’t be the reason we need to make new rulesbrbr14. Safety & Emergenciesbr- Smoke detectors and carbon monoxide alarms are installed and functioning — please do not disable them. If they are chirping due to a low battery, please notify us immediately (no one wants to listen to this all night). br- A fire extinguisher is located near the main level bathroom and near the fridge in the lower level kitchen. br- An evacuation map is posted in the unit.br- In case of emergency: Call 911 first, then contact us.brbr15. Damage, Breakages & Cleaningbr- We know accidents happen, especially when we’re having fun. Please report any damage, spills, or issues to us immediately (before checkout). This allows us to properly prepare to fix issues before the next guest checks in)br- Please use appliances and amenities as they are intended. We are certain that you are intelligent enough to know that toaster ovens shouldn’t be used as stepstools and vacuum cleaners shouldn’t be used to split firewood. Please don’t prove us wrong. You are responsible for any damage beyond normal wear and tear. br- We include professional cleaning in your rate, but excessive mess may result in additional fees.brbrFinal NotebrBy booking and staying with us, you and your party agree to these house rules, the rental agreement, and all applicable local and state regulations.brWe truly appreciate you helping us keep this special place beautiful for everyone who visits. If you have any questions at all, please don’t hesitate to reach out!brWishing you a fantastic Bayfield adventure — enjoy the hiking, kayaking, orchards, and the stunning Apostle Islands!brWarmly,brWindseeker Rentals Team

Hendrickson House - Downtown Bayfield, WI

Bayfield, Wisconsin, United States

Bed

3

Bath

10

Sleeps

$497.43

Enjoy a relaxing stay in this beautifully furnished vacation stay, part of a charming two-unit home in downtown Bayfield, WI. brbrThis cozy retreat features inviting living spaces, a fully stocked kitchen, and comfortable sleeping accommodations for up to 6 guests. Home features 2nd floor King bedroom, jacuzzi tub with Lake Superior views, and ensuite bathroom. Open concept main floor with dining room, living room, full bathroom, kitchen and great deck with Lake Superior views. Main floor sleeping includes Queen murphy bed (next to dining table) and full sleeper sofa. brbrJust steps from local shops, dining, and Bayfield’s waterfront attractions, it’s the perfect home base for exploring the Apostle Islands and everything this lakeside town has to offer. This unit can be rented along with the Carriage @ Hendrickson House (together in the Hendrickson House listing) to accommodate larger groups. brbrAll towels and linens included (please bring beach towels to enjoy the Big Lake). Sleeps up to 6. $25 / night / person after 4.brProperty Name: Main @ Hendrickson HousebrbrWELCOME!brThank you for choosing our cozy vacation property in beautiful Bayfield, Wisconsin — the gateway to the Apostle Islands! We’re thrilled you are here and we want your stay to be relaxing, enjoyable, and full of wonderful memories.brbrPlease treat this property like your own home (or like grandma is watching). These house rules could be summed up by simply saying: Take care of your friends and family. Clean up after yourself. Don’t break things. Be safe. Appreciate the amazing world around you.brbrUnfortunately, humanity has repeatedly proven that in order to keep everyone safe, protect the home for future guests, respect our neighbors, and ensure we stay in compliance with our governmental overlords (Wisconsin State Lodging Code (ATCP 72), Bayfield County Short-Term Rental Ordinance, and the local fire/municipal codes), we are legally required to put the following in writing.brbr1. Check-In & Check-OutbrCheck-in: After 4:00 PMbrCheck-out: By 10:00 AMbrbrA detailed welcome guide with codes, WiFi information, and helpful instructions will be available in your guest portal. If you’re arriving late, please let us know through the portal when you complete your online check-in form - we want to make sure you arrive and get into the unit without issue. brbrCheckout ProceduresbrThank you for helping us get the home ready for the next guests! Here’s what we ask:br- Leave by 10:00 AM so our cleaning team has enough time to prepare the property. - If you need a late checkout please reach out the day before you checkout for approval - we will do our best to accommodate all requests. Late check-out fees may apply. br- Wash any used dishes. Run the dishwasher upon departure. br- Tie up any trash and set out for housekeeping to remove after checkout. br- Check inside all drawers, check under the bed, check inside fridge, etc. to ensure you have all your belongingsbr- Unplug any counter appliances (i.e. coffee maker, toaster, etc.)br- Turn off all lightsbr- Leaves fans on lowbr- COLD MONTHS: Sept/Oct through April: Set Heat to 68 upon departure.br- WARM MONTHS: May through Sept: Set AC to 72br- Close and lock all windows and doors (especially the back door) - front door touch bottom of the keypad to lock upon departurebrbrA quick final walk-through helps us a lot — we truly appreciate it!brbr2. Maximum Occupancy & Guestsbr- Maximum overnight guests: 6 (based on bedding and local ordinances).br- If needed, pillows and blanket for the Murphy Bed are located in the white tote bags located in the laundry closet behind the couch. The key to unlock the bed is in that closet as well. Please read the instructions ON the bed prior to using. br- If needed, pillows and linens for the pullout couch are located in the white tote bag in the ottoman at the end of the couch. br- If you use the Murphy bed and/or the pullout couch, please leave the linens out (do not put away) - so we know they were used and these need to be watched. br- Day visitors are welcome but limited to no more than 4 at any time and must follow all house rules.br- No recreational vehicles, campers, tents, trailers, or additional lodging on the property.brbr3. Quiet Hours & Respect for Neighborsbr- Quiet hours: 10:00 PM – 8:00 AM daily (including weekends and holidays).br- Please keep noise to a respectful minimum at all times — no loud music, shouting, or gatherings that might disturb our neighbors.br- Fireworks are not permitted at any time.brbr4. Smoking & Vapingbr- This is a 100% smoke-free and vape-free property — inside and outside (including porches, decks, and yard).br- Violation will result in a minimum $300 deep-cleaning fee.brbr5. No Petsbr- No pets of any kind are allowed.br- If you have a service animal, please contact us in advance so we can make appropriate accommodations.brbr6. Parties & Gatheringsbr- No parties (including togas), events, weddings, receptions, or large gatherings.br- Small, quiet family gatherings are fine as long as they stay within occupancy limits and quiet hours.brbr7. Parkingbr- This unit is street parking only. br- Do not block neighbor driveways. br- Do not park on the lawn. brbr8. Bikes, Motorized Items & EV Chargingbr- No bikes or motorized items (including e-bikes, scooters, motorcycles, etc.) are permitted inside the house or unit.br- EV Charging Policy: We do not have a dedicated EV charger on the property. Plugging electric vehicles into any household outlets is not permitted due to safety and insurance reasons. Public EV charging stations are available in downtown Bayfield (less than 1 mile away).brbr9. ATVs, UTVs & Snowmobilesbr- These vehicles are not allowed to be used onsite at this property. We welcome you to bring these and enjoy the local trails, but will require travel to the trail heads. brbr10. Trash, Recycling & Septic Systembr- Use the provided trash bins inside the unit during your stay. If you are here for an extended stay and need additional trash removal, please notify us. br- Please do not flush wipes, feminine products, diapers, paper towels, grease, or food scraps down the toilets or drains (our septic/sewer system thanks you!).br- At the end of your stay, please tie up all trash and set it together for housekeeping to remove after departure. brbr11. Kitchen, Grill & Appliancesbr- Clean up after every usebr- Use appliances for their intended purpose.br- Private cookware is not permitted on decks or within 10 ft of structures. Please see grill for additional instructions for use. brbr12. Fireplaces & Fire Pitbr- Feel free to enjoy the gas fireplace inside during cooler months — just remember to turn it off when you’re done. (the pilot light should still remain on, even when the unit is off)br- There is not an outdoor firepit at this unit. brbr13. General House Rulesbr- Please remove shoes at the door.br- Do not move furniture.br- Please do not bring linens or towels outside (especially to the beach.)br- Please don’t climb on roofs, railings, trees etc.br- Please don’t be the reason we need to make new rulesbrbr14. Safety & Emergenciesbr- Smoke detectors and carbon monoxide alarms are installed and functioning — please do not disable them. If they are chirping due to a low battery, please notify us immediately (no one wants to listen to this all night). br- A fire extinguisher is located on the main floor near the bathroom. br- An evacuation map is posted in the unit.br- In case of emergency: Call 911 first, then contact us.brbr15. Damage, Breakages & Cleaningbr- We know accidents happen, especially when we’re having fun. Please report any damage, spills, or issues to us immediately (before checkout). This allows us to properly prepare to fix issues before the next guest checks in)br- Please use appliances and amenities as they are intended. We are certain that you are intelligent enough to know that toaster ovens shouldn’t be used as stepstools and vacuum cleaners shouldn’t be used to split firewood. Please don’t prove us wrong. You are responsible for any damage beyond normal wear and tear. br- We include professional cleaning in your rate, but excessive mess may result in additional fees.brbrFinal NotebrBy booking and staying with us, you and your party agree to these house rules, the rental agreement, and all applicable local and state regulations.brWe truly appreciate you helping us keep this special place beautiful for everyone who visits. If you have any questions at all, please don’t hesitate to reach out!brWishing you a fantastic Bayfield adventure — enjoy the hiking, kayaking, orchards, and the stunning Apostle Islands!brWarmly,brWindseeker Rentals Team

Main @ Hendrickson House

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$256.91

Looking for the perfect home base for your visit to Bayfield Look no further: this awesome ground floor condo has everything you could need for a truly memorable (and comfortable) vacation! This newly-remodeled one-bed condo features an open plan kitchen-dining-living space, plus a private balcony overlooking the lake (perfect for morning coffee or evening cocktails). The bathroom is clean and bright, and the kitchen is outfitted for all your culinary adventures!brbrYour host runs Bark Point Ventures, a vacation rental management & concierge company that specializes in properties all along Lake Superior's South Shore. We live nearby and is available whenever needed to assist our guests. Our passion is ensuring guests experience the magic of what we feel is one of the most amazing places in the world.brbrLocated on the beach right in downtown Bayfield. You can walk to a wide range of locally-owned shops, restaurants, galleries, and museums. And yet the condo is set far enough away from the main drag to not feel like you're too in the middle of everything. brbrOne parking space per unit is provided in the parking lot. Street parking is also readily available except during the fall Applefest celebration. brbrBayfield is a very walkable city, so your best bet is on foot. We are just a couple blocks from all the shops and restaurants in downtown Bayfield.brbrThe following shuttles and ferries are also accessible on foot from Reiten Boatyard:brbr - The Madeline Island Ferry will take you out to Madeline Island and runs regularly during the late spring, summer, fall, and much of the winter. brbr- The BART Bus runs regularly from through Bayfield and around Chequamegon Bay for a modest fee.brbr- Big Top Chautauqua runs shuttles for most of for their concerts and events.brbrThis ground level, one bedroom unit features an open plan kitchen-dining-living space that opens up to your own private balcony overlooking the lake (perfect for morning coffee or evening cocktails). You'll find the kitchen has the basics for your stay, but please note that the fridge is dorm-sized and while there is a stovetop, there is no full-size oven. The owners have provided a good-sized toaster oven as an alternative. The bathroom is updated and spacious. brbrThe unit also features a rarity in the area: air conditioning, as well as high-speed wifi. brbrDue to the lack of public transportation and the distance between towns/amenities, a car is pretty much essential. But, on the plus side, traffic is not a concept we have up here!brbrWalk to downtown shops and restaurants, ferry terminal and recreation center. brOff street parking in lot for one car. Plenty of street parking available, except during Applefest weekend in October. Less than 15 minute drive to Mt. Ashwabay ski hill, Big Top Chautauqua, hiking trails, beaches, and more.brbrPublic transportation on the peninsula is provided by the Bay Area Rural Transit (BART), more information can be found on their website.brbrAn EV charging station is located in the parking lot on the corner of Washington Ave. and E. 6th St. in Washburn.brbrBe aware that sound and vibration travel easily in this building. Please be considerate of your neighbors and keep voices and TV levels down and please walk softly on stairway as well as inside the condo. brThere are 2 picnic tables and 2 weber grills available for use by guests and residents of all units. brBike racks are also available by the parking lot.brSmoking of any kind, including e-cigs, is strictly prohibited either in or outside the condos or anywhere on the premises.br As much as we love dogs, canine guests are NOT allowed at this property. We're happy to help you locate a dog-friendly rental should you require one.

New Remodel Condo | Bayfield Harborside

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$209.44

If you love the peace and serenity of the woods but still appreciate having convenient access to town, then Woodland Lodging is the place to be! This charming & clean main floor apartment is nestled up in the woods on a quiet dead-end road just short a 5-minute drive to downtown Bayfield. Head down the hill into Bayfield for dining, shopping, beaches, and hiking. If golfing is your thing, just a 3-minute drive up the hill and you’ll find the gorgeous Apostle Highland Golf Course. brbrYour host runs Bark Point Ventures, a vacation rental management & concierge company that specializes in properties all along Lake Superior's South Shore. We live nearby and are available whenever needed to assist our guests. Our passion is ensuring guests experience the magic of what we feel is one of the most amazing places in the world.brbrNeighborhoodbrWoodland Lodging is located on a peaceful wooded lot, just a 5 minute drive to Bayfield's commercial district with a wide range of shops, restaurants, galleries, beaches and the ferry landing. The home sits on a quiet dead-end road and offers a peaceful escape with the convenience of being close to town. brbrSpace OverviewbrIf you love the peace and serenity of the woods but still appreciate having convenient access to town, then Woodland Lodging is the place to be! This charming property is nestled up in the woods on a quiet dead-end road just short a 5-minute drive to downtown Bayfield. Head down the hill into Bayfield for dining, shopping, beaches, and hiking. If golfing is your thing, just a 3-minute drive up the hill and you’ll find the gorgeous Apostle Highland Golf Course. brbrThis main floor unit of the duplex features an open plan living/dining/kitchen area with a comfy couch, 2 chairs, a dining table with seating for four, a fully-outfitted kitchen, and high-speed wifi that makes streaming your favorite content on the smart tv with Roku or your preferred device a breeze. The primary bedroom has a queen bed and the living room has a newer full-sized futon. The full bath has a combo tub/shower. The apartment is set up perfectly for 2 but can comfortably accommodate 2 additional small children or single adult on the futon in the living room. brIn the summer months there is an herb garden right off the front deck that guests are welcome to pick from. brbrTransitbrDue to the lack of public transportation and the distance between towns/amenities, a car is pretty much essential. But, on the plus side, traffic is not a concept we have up here!brbrCabin & Property Amenitiesbr-This unit is located on the main floor of Woodland Lodging- no steps makes for easy access! br-1 bedroom with a king-sized bed, a full-sized futon in the living room, and a full kitchen & bath.br- Dining seating for 4 br- High-speed wifi & smart TVbr-Sweet front porch from which to enjoy your morning coffee or evening cocktails from.br- Perfect location for exploring everything Bayfield has to offer!br As much as we love dogs, canine guests are NOT allowed at this property. We're happy to help you locate a dog-friendly rental should you require one.

Woodland Lodging | Apartment near Bayfield

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$214.21

Steeple Hill Flats offers two modern hotel-style suites nestled into the Bayfield hillside overlooking downtown and the breathtaking Lake Superior, Apostle Islands, and the Madeline Island Ferry. The Lower Flat is on the main level with gorgeous views and a walkout private balcony. Abundant in windows and natural light, this airy suite offer guests a chance to relax and rewind. Steeple Hill Flats is located in a quiet residential area, a short walk from everything downtown Bayfield has to offer. brbrUnit has Queen bed. Spalike amenities with large soaking tubs, luxurious robes, bath salts and Lake Superior views. Eating area offers a mini fridge with freezer, microwave, standard drip coffee maker, and a small table and chairs. Linens, towels and basic toiletries provided. Beach towels NOT included. There is a SmartTV and internet in the unit allowing accessibility to login to your own streaming channels, there is no cable. brbr*No pets, no exceptions.*brProperty Name: Steeple Hill Flats-Lower FlatbrbrWELCOME!brThank you for choosing our cozy vacation property in beautiful Bayfield, Wisconsin — the gateway to the Apostle Islands! We’re thrilled you are here and we want your stay to be relaxing, enjoyable, and full of wonderful memories.brbrPlease treat this property like your own home (or like grandma is watching). These house rules could be summed up by simply saying: Take care of your friends and family. Clean up after yourself. Don’t break things. Be safe. Appreciate the amazing world around you.brbrUnfortunately, humanity has repeatedly proven that in order to keep everyone safe, protect the home for future guests, respect our neighbors, and ensure we stay in compliance with our governmental overlords (Wisconsin State Lodging Code (ATCP 72), Bayfield County Short-Term Rental Ordinance, and the local fire/municipal codes), we are legally required to put the following in writing.brbr1. Check-In & Check-OutbrCheck-in: After 4:00 PMbrCheck-out: By 10:00 AMbrbrA detailed welcome guide with codes, WiFi information, and helpful instructions will be available in your guest portal. If you’re arriving late, please let us know through the portal when you complete your online check-in form - we want to make sure you arrive and get into the unit without issue. brbrCheckout ProceduresbrbrThank you for helping us get the home ready for the next guests! Here’s what we ask:br- Leave by 10:00 AM so our cleaning team has enough time to prepare the property. If you need a late checkout please reach out the day before you checkout for approval - we will do our best to accommodate all requests. Late check-out fees may apply. br- Wash & sanitize any glassware you may have used. Supplies are under the bathroom sink (please let us know if bleach is running low)br- Take all trash and recycling to the designated canisters outside the front door of the building-near the stepsbr- Check inside all drawers, check under the bed, check inside fridge, etc. to ensure you have all your belongingsbr- Turn off all lights.br- Leaves fans on low.br- COLD MONTHS: Sept/Oct through April: Set heat to 68 using thermostat. (Do not use minisplit/remote during the cold months). br- WARM MONTHS: May through Sept: Set air conditioning to 72 with remote. br- Close and lock all windows and doors - unit and exterior door touch bottom of the keypad to lock upon departurebr- A quick final walk-through helps us a lot — we truly appreciate it!brbr2. Maximum Occupancy & Guestsbr- Maximum overnight guests: 2 (based on bedding and local ordinances).br- Day visitors are welcome but limited to no more than 2 at any time and must follow all house rules.br- No recreational vehicles, campers, tents, trailers, or additional lodging on the property.brbr3. Quiet Hours & Respect for Neighborsbr- Quiet hours: 10:00 PM – 8:00 AM daily (including weekends and holidays).br- Please keep noise to a respectful minimum at all times — no loud music, shouting, or gatherings that might disturb our neighbors.br- Fireworks are not permitted at any time.brbr4. Smoking & Vapingbr- This is a 100% smoke-free and vape-free property — inside and outside (including porches, decks, and yard).br- Violation will result in a minimum $300 deep-cleaning fee.brbr5. No Petsbr- No pets of any kind are allowed.br- If you have a service animal, please contact us in advance so we can make appropriate accommodations.brbr6. Parties & Gatheringsbr- No parties (including togas), events, weddings, receptions, or large gatherings.br- Small, quiet family gatherings are fine as long as they stay within occupancy limits and quiet hours.brbr7. Parkingbr- Spaces available for 1 vehicle in the guest parking area near the entrance to the building. brbr8. Bikes, Motorized Items & EV Chargingbr- No bikes or motorized items (including e-bikes, scooters, motorcycles, etc.) are permitted inside the house or unit.br- EV Charging Policy: We do not have a dedicated EV charger on the property. Plugging electric vehicles into any household outlets is not permitted due to safety and insurance reasons. Public EV charging stations are available in downtown Bayfield (approximately 1 mile away).brbr9. ATVs, UTVs & Snowmobilesbr- These vehicles are not allowed at this property. We certainly welcome you to bring your toys, but there is not enough space in the parking area for trailers, etc. You are welcome to park on the side streets. Check local maps and ordinances for nearest trail access. brbr10. Trash, Recycling & Septic Systembr- Use the provided trash and recycling bins inside the unit during your stay.br- Please do not flush wipes, feminine products, diapers, paper towels, grease, or food scraps down the toilets or drains (our septic/sewer system thanks you!).br- At the end of your stay, please take all trash and recycling to the designated canisters outside at the front of the building near the steps. brbr11. “Kitchennette”, Grill & Appliancesbr- Clean up after every usebr- Use appliances for their intended purpose.br- There is no grill or fire pit at this property. brbr13. General House Rulesbr- Please remove shoes at the door.br- Do not move furniture.br- Please do not bring linens or towels outside (especially to the beach.)br- Please don’t climb on roofs, railings, trees etc.br- Please don’t be the reason we need to make new rulesbrbr14. Safety & Emergenciesbr- Smoke detectors and carbon monoxide alarms are installed and functioning — please do not disable them. If they are chirping due to a low battery, please notify us immediately (no one wants to listen to this all night). br- A fire extinguisher is located in the hallway of the shared entrance to the building. br- The evacuation map is on the back of your room door. br- In case of emergency: Call 911 first, then contact us.brbr15. Damage, Breakages & Cleaningbr- We know accidents happen, especially when we’re having fun. Please report any damage, spills, or issues to us immediately (before checkout). This allows us to properly prepare to fix issues before the next guest checks in)br- Please use appliances and amenities as they are intended. We are certain that you are intelligent enough to know that toaster ovens shouldn’t be used as stepstools and vacuum cleaners shouldn’t be used to split firewood. Please don’t prove us wrong. You are responsible for any damage beyond normal wear and tear. br- We include professional cleaning in your rate, but excessive mess may result in additional fees.brbrFinal NotebrBy booking and staying with us, you and your party agree to these house rules, the rental agreement, and all applicable local and state regulations.brWe truly appreciate you helping us keep this special place beautiful for everyone who visits. If you have any questions at all, please don’t hesitate to reach out!brWishing you a fantastic Bayfield adventure — enjoy the hiking, kayaking, orchards, and the stunning Apostle Islands!brbrWarmly,brWindseeker Rentals Team

Lower Flat @ Steeple Hill Flats, Bayfield

Bayfield, Wisconsin, United States

Bed

Bath

Sleeps

$393.6

Welcome to your cozy Bayfield escape! This charming unit, part of a well-maintained two-unit home in the heart of downtown Bayfield, is the perfect retreat for couples, small families, or friends looking to explore the best of Lake Superior’s south shore.brbrThe space sleeps up to 4 guests and offers a warm, inviting atmosphere with comfortable furnishings, natural light, and thoughtful coastal touches throughout. Enjoy a fully stocked kitchen with everything you need to prepare meals at home, plus a cozy dining area for relaxing after a day of adventure.brbrLocated just steps from Bayfield’s shops, restaurants, waterfront, and ferry to Madeline Island, this unit is an ideal home base for exploring the Apostle Islands, local orchards, and year-round events.brbrWhether you`re here for a weekend getaway or a longer stay, you’ll feel right at home in downtown Bayfield. All linens and towels included. brbrSleeps up to 4. $25 / night / person after 2.brProperty Name: Carriage @ Hendrickson House brbrWELCOME!brThank you for choosing our cozy vacation property in beautiful Bayfield, Wisconsin — the gateway to the Apostle Islands! We’re thrilled you are here and we want your stay to be relaxing, enjoyable, and full of wonderful memories.brPlease treat this property like your own home (or like grandma is watching). These house rules could be summed up by simply saying: Take care of your friends and family. Clean up after yourself. Don’t break things. Be safe. Appreciate the amazing world around you.brbrUnfortunately, humanity has repeatedly proven that in order to keep everyone safe, protect the home for future guests, respect our neighbors, and ensure we stay in compliance with our governmental overlords (Wisconsin State Lodging Code (ATCP 72), Bayfield County Short-Term Rental Ordinance, and the local fire/municipal codes), we are legally required to put the following in writing.brbr1. Check-In & Check-OutbrCheck-in: After 4:00 PMbrCheck-out: By 10:00 AMbrbrA detailed welcome guide with codes, WiFi information, and helpful instructions will be available in your guest portal. If you’re arriving late, please let us know through the portal when you complete your online check-in form - we want to make sure you arrive and get into the unit without issue. brbrCheckout ProceduresbrThank you for helping us get the home ready for the next guests! Here’s what we ask:br- Leave by 10:00 AM so our cleaning team has enough time to prepare the property. - If you need a late checkout please reach out the day before you checkout for approval - we will do our best to accommodate all requests. Late check-out fees may apply. br- Wash any used dishes. Run the dishwasher upon departure. br- Please bag all garbage and set out for housekeeping to remove. br- Check inside all drawers, check under the bed, check inside fridge, etc. to ensure you have all your belongingsbr- Unplug any counter appliances (i.e. coffee maker, toaster, etc.)br- Turn off all lightsbr- Leaves fans on lowbr- COLD MONTHS: Sept/Oct through April: Set Heat to 68 upon departure.br- WARM MONTHS: May through Sept: Set AC to 72br- Close and lock all windows and doors (especially the back door) - front door touch bottom of the keypad to lock upon departurebrbrA quick final walk-through helps us a lot — we truly appreciate it!brbr2. Maximum Occupancy & Guestsbr- Maximum overnight guests: 4 (based on bedding and local ordinances).br- If needed, pillows, mattress protector and linens for the futon in the Carriage unit are in the bench seat/chest. Please put the mattress protector down first then add the fitted sheet. Upon checkout-leave used linens out for housekeeping removal. br- Day visitors are welcome but limited to no more than 2 at any time and must follow all house rules.br- No recreational vehicles, campers, tents, trailers, or additional lodging on the property.brbr3. Quiet Hours & Respect for Neighborsbr- Quiet hours: 10:00 PM – 8:00 AM daily (including weekends and holidays).br- Please keep noise to a respectful minimum at all times — no loud music, shouting, or gatherings that might disturb our neighbors.br- Fireworks are not permitted at any time.brbr4. Smoking & Vapingbr- This is a 100% smoke-free and vape-free property — inside and outside (including porches, decks, and yard).br- Violation will result in a minimum $300 deep-cleaning fee.brbr5. No Petsbr- No pets of any kind are allowed.br- If you have a service animal, please contact us in advance so we can make appropriate accommodations.brbr6. Parties & Gatheringsbr- No parties(including togas), events, weddings, receptions, or large gatherings.br- Small, quiet family gatherings are fine as long as they stay within occupancy limits and quiet hours.brbr7. Parkingbr- Parking is available for up to 2 vehicles in the designated driveway.br- Please do not block the driveway or neighbors’ access.br- No parking on the grass or lawn.br- Limited street parking is also available.brbr8. Bikes, Motorized Items & EV Chargingbr- No bikes or motorized items (including e-bikes, scooters, motorcycles, etc.) are permitted inside the house or unit.br- EV Charging Policy: We do not have a dedicated EV charger on the property. Plugging electric vehicles into any household outlets is not permitted due to safety and insurance reasons. Public EV charging stations are available in downtown Bayfield (approximately 1 mile away).brbr9. ATVs, UTVs & Snowmobilesbr- These vehicles are not allowed at this property.brbr10. Trash, Recycling & Septic Systembr- Use the provided trash bins inside the unit during your stay. If you are here for an extended stay and need additional trash removal, please notify us. br- Please do not flush wipes, feminine products, diapers, paper towels, grease, or food scraps down the toilets or drains (our septic/sewer system thanks you!).br- At the end of your stay, please tie up all trash and set it together for housekeeping to remove after departure. brbr11. Kitchen, Grill & Appliancesbr- Clean up after every usebr- Use appliances for their intended purpose.br- Private cookware is not permitted on decks or within 10 ft of structures. There is NOT a grill provided at this unit. brbr12. Fireplaces & Fire Pitbr- There is not a fire pit or fireplace in this unit. brbr13. General House Rulesbr- Please remove shoes at the door.br- Do not move furniture.br- Please do not bring linens or towels outside (especially to the beach.)br- Please don’t climb on roofs, railings, trees etc.br- Please don’t be the reason we need to make new rulesbrbr14. Safety & Emergenciesbr- Smoke detectors and carbon monoxide alarms are installed and functioning — please do not disable them. If they are chirping due to a low battery, please notify us immediately (no one wants to listen to this all night). br- A fire extinguisher is located in the kitchen next to the refrigerator.br- An evacuation map is posted in the unit.br- In case of emergency: Call 911 first, then contact us.brbr15. Damage, Breakages & Cleaningbr- We know accidents happen, especially when we’re having fun. Please report any damage, spills, or issues to us immediately (before checkout). This allows us to properly prepare to fix issues before the next guest checks in)br- Please use appliances and amenities as they are intended. We are certain that you are intelligent enough to know that toaster ovens shouldn’t be used as stepstools and vacuum cleaners shouldn’t be used to split firewood. Please don’t prove us wrong. You are responsible for any damage beyond normal wear and tear. br- We include professional cleaning in your rate, but excessive mess may result in additional fees.brbrFinal NotebrBy booking and staying with us, you and your party agree to these house rules, the rental agreement, and all applicable local and state regulations.brWe truly appreciate you helping us keep this special place beautiful for everyone who visits. If you have any questions at all, please don’t hesitate to reach out!brWishing you a fantastic Bayfield adventure — enjoy the hiking, kayaking, orchards, and the stunning Apostle Islands!brWarmly,brWindseeker Rentals Team

Carriage @ Hendrickson House

Bayfield, Wisconsin, United States

Bed