Home Vacation Rentals By Owner In Sister Bay, WI

Showing 40 Of 145 Vacation Rentals
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Exceptional(10)

$1035.11

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Private Vacation Home

Perfect for Families: Three Ensuites, Game Room & Unique Kids Outdoor Play Area

Sister Bay, Wisconsin, United States

Welcome to Chicory Hill – a luxurious and authentic Door County retreat designed for family fun and relaxation.brbrEscape to the beauty and charm of Door County, Wisconsin! At Chicory Hill, we invite you to relax and recharge. Whether you are friends coming together to celebrate a long-lasting bond, or a family uniting across generations to create unforgettable moments, we offer the ideal vacation retreat for meaningful connection. Experience meticulous attention to detail and thoughtfully curated spaces designed to make you feel at home. Let us be the backdrop to your next adventure and the place where memories are made. brbrWe've designed Chicory Hill for those who want to be conveniently located near Door County’s many attractions while enjoying an exceptional guest experience in a private, modern escape. Revel in the comfort of ensuite bathrooms in every bedroom, a cozy indoor fireplace, a game room for all ages, and thoughtfully curated outdoor amenities.brbr★OUR CLEANING PROTOCOLS SET US APART★brChicory Hill is proudly family-managed and personally cared for. Because we oversee every stay ourselves, we maintain the highest standard of cleanliness. We understand how much cleanliness impacts your vacation experience. At Chicory Hill, we go beyond standard turnover practices by laundering all duvet covers, living room throw blankets, and throw pillow covers between every guest, along with all bed linens and pillowcases. Our goal is to provide a welcoming, meticulously maintained home where you can truly relax and enjoy your stay with confidence and peace of mind.brbrWHY STAY AT CHICORY HILL brDoor County is a world-class vacation destination, and we truly believe that Chicory Hill has every ingredient necessary to make lasting, generational vacation memories. Attention to detail is our calling card at ChicoryDoorCounty. At Chicory Hill, you'll find recliners and reclining sofas in our living room, because we furnish our homes for people, not for social media photos. Relax together with a few glasses of wine and listen to some vinyl records. Have breakfast or read a good book on our classic farmhouse porch. Enjoy some friendly competition in our game room. Watch your little ones discover the whimsy of our outdoor natural play area. Chat and reminisce next to our fire table or spend precious family evenings cozying up to a roaring bonfire. With an indoor gas fireplace, a private outdoor entertaining space, and a game room complete with children's toys, bumper pool, and classic video games, Chicory Hill is the perfect place to relax and make memories for all ages and seasons.brbrENJOY AN ENSUITE BATHROOM IN ALL THREE BEDROOMSbrOur home has three suites – each with a new, luxurious ensuite bathroom.br•The primary, main-floor bedroom has a King bed, a stunning walk-in shower with a tile surround and rain shower head, and a double vanity.br•The large, second-floor King suite has a King bed and a full-sized daybed. This suite also features a brand-new tile shower with a rain showerhead and a double vanity.br•The second-floor Queen suite has a Queen bed and a newly remodeled bathroom with a tub/shower combination and a gorgeous single vanity.br•The main floor also has a powder room.brbrGAME ROOM AMENITIESbrYoung or young-at-heart, there’s something for everyone at Chicory Hill! The amenities for you to enjoy in our game room include:br•65 Roku TV with a comfortable seating areabr•Table with seating for sevenbr•Children’s play area, table, toys, games, and booksbr•Bumper poolbr•Dutch Shuffleboardbr•One-Up Pac-Mania and Marvel Video gamesbr•Board games, cards, and cribbagebrbrYOUR LITTLE TRAVELERS WILL LOVE THE ONE-OF-A-KIND, WISCONSIN-THEMED, NATURAL PLAY AREAbrAt ChicoryDoorCounty, we believe vacationing with kids should be fun, not stressful. We’ve created a unique, natural outdoor play area including a real sunken rowboat for pretend play, a dry riverbed, a pea-gravel truck/digging area, and an adorable barn playhouse with hand-carved wooden farm animals to “feed”.brbrOUTDOOR AMENITIESbrChicory Hill has a large backyard with an amazing outdoor space for your enjoyment:br•A large wood-burning fire pit with seven Adirondack chairs and complimentary firewoodbr•An original farmhouse covered (open) back porch with a bistro table and seatingbr•Patio dining table with seven chairs located under our covered, open-air gazebobr•Propane fire table with patio seating - propane providedbr•Gas grill with propane providedbr•Access to detached garage, which contains marshmallow forks and outdoor games, including Corn hole, Ladder golf, and Yardzee. (Our garage is old and small. It is not suitable for vehicle parking.)brbrMORE DETAILS ABOUT CHICORY HILLbrChicory Hill is a classic Door County farmhouse that underwent complete restoration and remodel in 2024. Our home is two stories and 2,200 feet.br•Seven guests maximum - due to one of our beds being a daybed, a maximum of six adults is permitted.br•Our new kitchen is gorgeous, modern, and fully equipped with a dishwasher, induction stove, and refrigerator/freezer with ice maker. We also provide a traditional coffee maker, a Keurig, a coffee bean grinder, and an electric tea kettle. Also available are induction pots and pans, a toaster, a crock pot, a blender, kitchen towels, hot pads, baking pans, baking sheets, and BBQ utensils. Dishes, utensils, children’s dishes, glassware, wine glasses, and additional barware are also on site.br•Large dining table with seating for seven guestsbr•Indoor gas fireplacebr•Central heating and air conditioningbr•Washer and dryer on main level (free)br•Record player and vinyl music librarybr•Five Roku smart TVs (One in each bedroom, one in the living room, and one in the basement game room)br•Complimentary streaming app for live, local television, cable channels, and sports br• High-speed internet. (Due to the rural nature of Door County, Wi-Fi and cell phone coverage and service can vary)br•Three parking spots in driveway maximum (Village-controlled and enforced). No garage access for vehicles.br•No pets, fireworks, firearms, smoking, tobacco, or vaping allowed on property.brbrbrIMPORTANT DETAILS WE’D LIKE TO MENTIONbr•Chicory Hill is located on the south end of Sister Bay, not far from Pirates Cove Adventure Golf. Guests may hear laughter, joy, and music while using the outdoor spaces of our home. We are also conveniently located one lot removed from South Bayshore Drive (State Trunk 42). Like most locations on our peninsula, some vehicle noise will be heard outside. We have a six-foot privacy fence and a tree line in our backyard, adjacent to our outdoor entertainment space. We have a couple of reviews in which guests mention that our home is walkable to downtown Sister Bay. While this is technically true, guests should be aware that there is a large, long hill leading into downtown from our home. This may present difficulty when walking back to Chicory Hill for some of our guests. South Sister Bay locations, including Peach Barn Brewery, Johnson's Fun Park, Pirates Cove mini-golf and Piggly Wiggly Grocery Store, are an easy walk from Chicory Hill. brbr•Please note that Chicory Hill is a remodelled classic farmhouse. We have slanted ceilings around our upstairs beds. At the end of our basement stairwell, there is a small section with a slightly low ceiling height, requiring guests to duck their heads. Because we added central heating and cooling during restoration, our basement ceiling has areas that are slightly lower than modern basements. Guests taller than 6'3 may need to slightly duck in some areas.brbrbr★WE GENUINELY LOOK FORWARD TO HOSTING YOU★brChicoryDoorCounty is run by our family, and we truly care about your experience while staying with us. Please let us know if there's anything we can do to help you have a terrific Door County getaway. Many of the requirements in our house rules are dictated by our local village’s short-term rental ordinance and are beyond our control. Our standard check-in time is 4:00 p.m., and our standard check-out time is 10:00 a.m.brPlease read our entire listing, including our house rules and the description of our home's location. We require a signed rental agreement and a $300 credit card security deposit hold for all bookings. To finalize the booking and prevent cancellation, we require that our guests read and sign the agreement before their free cancellation period expires. Furniture and decor may differ from the listing photos, as we strive to maintain the comfort, quality, and cleanliness of our home's furnishings.
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Bath 3

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Sleep 7

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$834.24

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Private Vacation Home

Contemporary Northwoods Retreat- In the Heart of Sister Bay

Sister Bay, Wisconsin, United States

Welcome to Trillium Timbers, a thoughtfully designed Contemporary Northwoods–style home tucked into the trees just moments from the heart of Sister Bay. Elevated among a wooded lot, this inviting retreat blends modern comfort with the natural beauty that makes Door County unforgettable.brbrStep out onto the second-story deck and take in peaceful views overlooking the yard and surrounding woods—your own private perch for morning coffee or unwinding after a day of exploring. A short walk down the hill brings you to Highway 42, and you’re just a 2-minute drive to the Sister Bay Marina, beach, dining, and shops..brbrTHE SPACEbr-Comfortably Sleeps 10br-3 private bedrooms + bonus bunk roombr-2.5 bathroomsbr-Kid`s Recreating Room with Smart TV and Video Gamesbr-Ideal for families or multiple couples traveling togetherbr-Each bedroom is equipped with a large Smart TV, offering a comfortable and private space to relax at the end of the day.brbrBEDROOM LAYOUT.br-Bedroom 1- Kingbr-Bedroom 2- Queenbr-Bedroom 3- Queenbr-Bedroom 4/Room off the Master- Two sets of Twin Bunk Beds (4 twin`s total) brbrOUTDOOR LIVINGbr-Private Fire Pit with Adirondack Chairsbr-Two Verandas with Wooded ViewsbrbrWHY TRILLIUM TIMBERSbr-Contemporary Northwoods design with warm, modern finishesbr-Elevated deck with serene wooded viewsbr-Rec room for kids and family downtimebr-Walkable access to Hwy 42br-Minutes from Sister Bay Marina, waterfront, dining & attractionsbrbrWhether you’re planning a summer getaway, fall color escape, or a cozy off-season retreat, Trillium Timbers offers the space, location, and comfort to make your Door County stay feel effortless and memorable.brbrYOUR HOSTSbr-When you stay with Northern Door Vacations, you’ll enjoy truly personalized, local service—no call centers, no robots—just a real Door County team who answers every call and text, before and during your stay. NDV — where vacations feel personal.brbrNOTESbr-To ensure a seamless check-in experience, guests are required to review and sign our standard rental agreement and complete a quick check-in form prior to arrival. This helps us comply with local regulations and provide the best possible stay.br-In an effort to keep the entire property more secure, the house is equipped with a ring doorbell camera to monitor the driveway and the front entry.br-Although we have a relaxed cancellation policy, we still incur the 4% cc fee. Your refund will be in full, minus the 4% cc fee. This is detailed in the guest contract.brNOTESbr-To ensure a seamless check-in experience, guests are required to review and sign our standard rental agreement and complete a quick check-in form prior to arrival. This helps us comply with local regulations and provide the best possible stay.br-Although we have a relaxed cancellation policy, we still incur the 4% cc fee. Your refund will be in full, minus the 4% cc fee. This is detailed in the guest contract.br-The primary renter must be 25 years or older.
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Bath 3

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Exceptional(2)

$785.13

/ Nightly
Private Vacation Home

The Best Kept Secret ! SisterBay

Sister Bay, Wisconsin, United States

pLocation! Location! Location! This Best Kept Secret is located in the heart of Sister Bay within walking distance to the beach, restaurants, ice cream, shops, breweries and more. If you love to fish or boat, there's a public boat ramp right around the corner and if you don’t have a boat you can sign up for a boat tour! Single story home, beautifully designed and decorated. Offers spacious bedrooms and living areas with great attention given to comfort and style. This 3 bedroom (5 beds) and 2 full baths, single story home, beautifully designed and decorated. Offers spacious bedrooms and living areas with great attention given to comfort and style.br- A fully equipped kitchen with stainless steel appliances br- 1 king bed, 3 queen beds, 1 twin bedbr- Full-size washer and dryer are inside the home.br- Smart TVs, ready to use with your own Netflix. etcbr- Outside patio with table and seating for 6br- Grill with grilling utensilsbr- Outdoor lawn gamesbr- Beach chairs, towels, beach bag, sand toys, and wagon to haul your goodies to the beachbr/pbrbrpEnjoy the modern amenities with a little cherry flair! This Door county home is the perfect getaway spot for families or small groups of friends looking to relax and unwind. It offers backyard privacy for a cookout or a game of bean bag toss. Settle down after a long day exploring Door County by streaming your favorite shows, breaking out the board games or snuggling up with a cherry blanket to read a good book. br/p
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Bath 2

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Sleep 9

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Exceptional(17)

$909.55

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Chalet

Modern Chalet With Stunning Forest Views

Sister Bay, Wisconsin, United States

Lakewood Lodge is a striking modern chalet set on five private wooded acres just outside Sister Bay. The architecture is truly stunning, with soaring floor to ceiling windows that rise nearly 30 feet tall and frame uninterrupted views of the surrounding woods and on site pond. Natural light fills the home throughout the day, creating a dramatic yet peaceful space that feels elevated and deeply connected to nature. Despite the sense of seclusion, the home is located just minutes from dining, shops, and the waterfront.brbrLakewood Lodge Highlightsbr• 3 spacious bedrooms with 2 Kings and 1 Queenbr• 3 full bathrooms including walk in showers and a jacuzzi whirlpool tubbr• Central air conditioning and heating for year round comfortbr• Fully equipped kitchen with modern appliancesbr• Cozy living room with gas fireplace and chalet style bay windowsbr• Two season sunroom with wood burning fireplacebr• Dedicated workspace with reliable high speed Wi Fibr• Expansive back deck with gas grill and Adirondack seatingbr• Fire pit area for evenings under the starsbr• Five private wooded acres with a small on site pondbr• Pet friendly. One time pet fee appliesbr• Full size washer and dryer and ample off street parkingbrbrBedrooms and BathroomsbrThe primary bedroom is a peaceful retreat featuring a king bed, bay windows overlooking the woods, and a private balcony for morning coffee. It includes a 65 inch Smart TV and a private en suite bathroom with walk in shower, jacuzzi whirlpool tub, and vanity.brbrThe second upstairs bedroom also features a king bed, a private balcony with wooded views, and its own en suite bathroom with walk in shower and vanity. A 65 inch Smart TV and spacious closet add extra comfort.brbrThe third bedroom, located on the main floor, offers a comfortable queen bed, a closet, and a private patio door leading outside. A full bathroom with walk in shower and vanity is located just down the hall.brbrAll bedrooms feature hospitality grade mattresses, luxury linens, and king size pillows for restful nights. Bathrooms are stocked with allergy free, eco friendly toiletries including shampoo, conditioner, body wash, lotion, and hand soap. Hairdryers are provided for guest use.brbrKitchen and Living SpacesbrThe open concept kitchen is fully stocked with everything needed for home cooked meals, including an oven and stove, microwave, dishwasher, toaster, and a 12 cup coffee maker. Expansive counter space and essential cookware make it easy to gather around the dining table and enjoy meals together.brbrThe main living room showcases chalet style bay windows and dramatic ceiling height with beautiful views of the surrounding woods and pond. Comfortable seating, a Smart TV, and a gas fireplace make it the perfect space for relaxing after a day exploring Door County.brbrOutdoor LivingbrThe two season sunroom offers a peaceful place to unwind with a stone wood burning fireplace, soft seating, and screened windows that let in the sounds of nature. Step out onto the expansive back deck to grill dinner, relax in Adirondack chairs, or head down to the fire pit for a cozy night under the stars.brbrThe property’s five private acres include a small, shallow pond that adds to the tranquil setting. This pond is not intended for swimming, but provides a beautiful natural backdrop and a sense of true seclusion.brbrGatherings at the PropertybrPlease note that parties, gatherings, and events are not permitted at the property. This includes picnics, family reunions, rehearsal dinners, and any event exceeding the home’s maximum occupancy, as it's prohibited by local short-term rental ordinances.brbrSafety and ComfortbrLakewood Lodge is equipped with smoke alarms, carbon monoxide detectors, and fire extinguishers for guest safety. Exterior cameras monitor the driveway and back deck for security purposes only.brbrLocation NotesbrLakewood Lodge is located approximately seven minutes from downtown Sister Bay. Due to the rural setting, driving is required, and walking or biking along County Road ZZ is not recommended.brbrBooking and Stay InformationbrGuests enjoy full access to the entire home and property. Entry is via a smart lock with a unique access code generated for each stay, allowing for easy self check in. There is no lengthy checkout list. Simply pack up and head out when your stay concludes.brbrAfter booking, guests will be guided through a secure process to sign a rental agreement and upload a photo ID to confirm age requirements. Accidental damage protection is included in place of a traditional security deposit. All payments remain on Airbnb.
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Bath 3

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Sleep 6

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Exceptional(25)

$844.35

/ Nightly
Cabin

Newly Updated Log Home on 5 acres - Gorgeous Decor and Family Friendly

Sister Bay, Wisconsin, United States

Welcome to The Great Escape, hosted by Simple Life Rentals! This custom-built log home has been updated throughout and offers private land, views of the bay and is just minutes from downtown Sister Bay. Enjoy sitting on the front porch or overlook the expansive view from the two balconies this home offers. The sun-filled property offers an open concept great room with vaulted ceilings, wood beams, exposed log wall and beautiful stone floor-to-ceiling fireplace. Additionally, the home includes first and second floor bedrooms and bathrooms, a second-floor loft area with a sectional sofa that opens to a full size bed, a full kitchen with snack bar, dining area and work desk as well as first floor laundry. The 5 acres of land provides guests a private retreat as they enjoy the central location to explore all the beauty and adventure Door County has to offer.brbrUpdates:brUpdated kitchen counters, backsplash, appliances, flooring, and new furniture.brAll new exterior paint showcasing this gorgeous log home.brNew windows, new roof, and more!brAir conditioning (mini split units)brNew driveway and landscaping coming in 2024.brbrProperty Features: br+ Snack bar (seating for 3)br+ Desk and chair (main great room)br+ 2 balconies (one off living room and one off second floor bedroom)br+ Front porch includes 2 rocking chairs and small tablebr+ 2 TVs (1 Smart TV includes DVD player), Owner offers Netflix and Amazon Prime for guestsbr+ Portable fanbr+ Patio table and 4 chairsbr+ Charcoal grill (guests supply own charcoal)br+ Iron, ironing board and drying rackbr+ Wi-Fi Starlink, supports virtual meetingsbr+ Pack 'n play and child's bedbr+ 2 strollersbr+ 2 baby safety gatesbr+ Games, DVDs, books, and children's beach toys for your enjoymentbr+ Central heat, Air-conditioning split units br+ Washer/ dryer combobr+ Fully equipped kitchenbrbrSleeping Accommodations:brBedroom 1: (main level): 1 Queen and 1 Twin bed, Smart TV with DVD player, Pack 'n Play and child's bed (in closet)brBedroom 2: (upper level): Queen bed, ensuite bathroom, adjoining loft separated by pocket door, escape ladder and private balconybrbrLoft: Second floor, sofa sleeper opens into a full bed, adjoins to bedroom #2 and is separated by pocket door, open to the first-floor great roombrbrBathrooms:brBathroom 1: (main level): Full bathroom with walk-in shower, hair dryerbrBathroom 2: (upper level) Full bathroom with walk-in shower, hair dryer, connected to bedroom #2brbrOutdoor Space:brFront porch includes 2 rocking chairs and small tablebrBalcony off living room includes table and 4 chairsbrBalcony off second floor bedroombrCharcoal grill (guests supply own charcoal)brAlmost 5 acres of landbrbr Amenity + damage protection waiver includes:br• Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels) br• A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom. br• PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).brbrHome truths: brOutdoor cameras: Ring camera door bell, second camera facing the driveway with motion-controlled spotlight, and a backyard camera.brDriveway gate to secure property when vacant.brbrThis home is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors and municipal restrictions, we cannot accommodate parties at the property including bachelor or bachelorette parties, reunions, weddings, or other gatherings. br brProperty is equipped with a decibel and smoking monitoring sensor located inside and outside of the home. br brDoor County Tourism Zone Commission Permit #32-56-2738-07brbrPlease be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.
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Bath 2

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Sleep 7

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Exceptional(26)

$1133.36

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Cabin

A Classic Waterfront A-Frame on Rowley’s Bay

Sister Bay, Wisconsin, United States

This Door County a-frame is perfect for hosting 2 to 3 families. Enjoy 3 bedrooms each with a queen bed as well as a loft featuring 4 twin trundle beds offering 11 beds total in the cabin. There are 1.5 bathrooms, a fully equipped kitchen, air conditioning, fireplace, sheets, towels, wifi, grill, stocked with family games, a washer and dryer, smart tvs, firepit, kayaks, and the best part: dogs welcome — everything you could ever need or want for the perfect Door County getaway.brbrYou’ll find shallow swimming and sandy shores for kids and a spacious deck to enjoy watching your kids make memories looking out on one of Door County’s most epic view of Rowleys Bay. Enjoy coffee and a stunning sunrise each morning as you start your day.brbrBuilt in 1969, this waterfront a-frame is not short on charm from the wood-burning fireplace, to the lofted a-frame ceiling, there’s just something extra cozy about this cabin you need to experience to understand.brbr*Dogs welcome for $150/dog (up to 3 - we wouldn’t leave our buddy home from a trip to the lake and wouldn’t ask you to, either!)br*Maximum of 10 people (Children under 3 are FREE)br*Fully equipped kitchen br*Fireplacebr*1.5 bathsbr*Washer + dryerbr*Sheets + towelsbr*Fire pit + adirondacksbr*Grillbr*Smart tv'sbr*Wifibr*DeckbrbrInterested in checking out our other properties Check out our other cabins from our profile: brbrThe Point: Our first cabin on Clark Lake that started it all.brWhen the best Clark Lake property on its own peninsula became available, we knew we had to find a way to make it ours! We couldn't be prouder to be the owners of The Point and share this slice of heaven with you. Think of it as high-end cabin comfort, with more than 1,200 feet of lakefront land and plenty of room for larger groups. Sleeps up to 15.brbrPorte Haven: Luxury waterfront cabin in northern Door CountybrSet on a Lake Michigan bluff at the very tip of the Door County Peninsula, Porte Haven feels like you're actually on a boat with views that are beyond spectacular: you see 4 islands, and the Washington Island Ferry goes by every hour. Enjoy an upscale cabin built on top of an old boathouse and hosts groups with a maximum of 6 adults (kids welcome too) and feels very private, but there's also an energy and vastness to all that's happening on the water surrounding it.brbrThe Bay: A modern-eclectic cabin with full views of Clark Lake.brJust 10 doors down from The Point, The Bay is warm and inviting, with cozy-chic interiors, a pellet stove and fire pit, shallow swimming for kids by the dock, and an amazing and spacious deck with a farm table and patio furniture to enjoy one of Door County's unbelievable sunsets. It has everything you could want for an unforgettable lake getaway. Sleeps up to 8, maximum of 6 adults.brbrWe can't wait to host your next family getaway!brJeremy and Caitlyn JefferybrDoor County Cabin Collective
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$253.58

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Apartment

Perfect Retreat for 2 | Studio Above Bakery, Dogs!

Sister Bay, Wisconsin, United States

Bird's Nest by Getaway and StaybrbrRelax in this cozy second-floor studio near downtown Sister Bay, in the heart of Door County, Wisconsin. Enjoy a private entrance, spacious balcony, and peaceful setting perfect for morning coffee or snowy sunset views. Located above Cultured sourdough bakery, wake to the comforting aroma of fresh bread. A noise machine ensures restful sleep. Walk to shops, dining, and Sister Bay Beach, and enjoy a quiet winter getaway with true local charm.brbr● 4 min drive to Downtown Sister Baybr● 4 min drive to Sister Bay Marinabr● 4 min drive to Al Johnsons’s Swedish Restaurant & Butikbr● 4 min drive to Sister Bay Beachbr● 9 min drive to Seaquist Orchards Farm MarketbrbrPROPERTY HIGHLIGHTSbr● Sleeps 4, 572 sq ft Cozy Studiobr● Just a 4-minute drive to downtown!br● Dogs allowed—bring your furry friends!br● 1 Bedroom and 1 Sleeper Sofabr● 1 Full-size bathroombr● Modern open living space for family funbr● Fully equipped kitchen br● Free high-speed internet br● Charcoal Grillbr● Fire PitbrbrExpect a five-star stay with us. We have a full digital concierge to assist with booking activities, reservations, and more.brbrCurious about our cleaning fee While ours might be slightly higher than others, we believe it's worth it for the quality experience we provide. Take a moment to read through and learn how it contributes to an exceptional stay! brbr★ MAIN STUDIO ★brbrOnce you open the upper floor doors, you'll enter immediately into this studio's core - we've got our washer and dryer here in an enclosed space, then next is our fully stocked kitchen including a sink, stove, and oven, full-size refrigerator, coffee machine; all for use when inside. This place also includes dishes (including silverware) and cookware to make breakfast or dinner for yourself during your stay. brbrWalk right past the kitchen, there sits a spacious dining table by windows looking out over trees - perfect for eating while taking in nature! Past the dining area is our bright bedroom space configured with a large King bed. On the other side of this space, there you'll find the living area with a full size sleeper sofa & flat screen TV tucked away in one corner; what comes next Well just beyond it all is our full-size bathroom just waiting for its next guest.brbrThis unique and tranquil home in the heart of Door County is designed especially for couples, or perhaps a couple with 1-2 young children. With its unique design, this studio provides an open space living and dining area and a fully-equipped kitchen perfect for your intimate relaxation. It is a wonderful place to be alone and unwind, and yet a short distance to all that Northern Door County has to offer! brbrPlease note that our vacation rental is located above a live bakery, which may result in some delicious aromas wafting into the space. While we hope that you enjoy the scent of fresh-baked goods, we also understand that it may not be for everyone. Therefore, we have taken measures to minimize any potential disruptions to your stay. We have provided an air purifier to help with any lingering bakery smells, as well as a white noise machine to mitigate any early morning noise. We hope that these amenities will ensure that you have a comfortable and enjoyable stay with us. brbrOUTDOORSbrEnjoy a relaxing evening in our backyard with a cozy fire pit. It's perfect for roasting marshmallows, sharing stories, or simply unwinding under the stars. A great addition to your stay, offering a warm and inviting space to gather with family and friends.brbrCULTURED (Sourdough Bakery)brIndulge in specialty sourdough bakery, where mouthwatering bagels, bread, and a delightful selection of fermented goodies like sauerkraut and kimchi are crafted. Visit their newly opened storefront every Friday to Sunday for a delicious experience (Please check their Social Media Pages for updated hours). Enjoy tempting bagel sandwiches, paired with aromatic drip coffee, while relaxing in our inviting outdoor seating area.brbr★ HOUSE RULES & OTHER POLICIES ★brbrPETS brWe warmly welcome up to 2 dogs to join your stay! There is a $75 fee per dog. If you're bringing more than one, please let us know in advance. To ensure a pleasant experience for everyone, we kindly ask that you bring waste bags and clean up after your pets, helping us keep the property in great shape for all guests. brbrPARKINGbrThis property features a spacious driveway that comfortably accommodates up to 2 cars or trucks, ensuring your family has plenty of parking options. Please remember to keep the grass pristine by parking only on the driveway. brbrSECURITY FEATURESbrTo ensure the safety and peace of mind of our guests, we have several security features in place, including multiple locks, loud audible alarms that are easy to activate, and an exterior security camera. These measures are designed to enhance security and provide a worry-free stay.brbrNEIGHBORHOOD brThis home is in a residential neighborhood. The neighborhood and backyard are perfect for grilling out, enjoying a fire, and laughing with your friends and family. Please respect our friends and neighbors and avoid loud, large parties. Please treat the neighbors like you live there. brbrSMART STAY AND EASY CHECK-INbrTo make your arrival as smooth and stress-free as possible, we use a secure digital guest portal powered by SuiteOp—no app needed. Before your stay, you’ll receive a simple link to complete a quick ID verification, choose between a refundable security deposit or a low-cost damage waiver, and sign the rental agreement.brbrThis helps us keep everything safe and secure while giving you a faster, contactless check-in experience. Once you’re set, you’ll have everything you need in one place—your door code, check-in details, house guide, local tips, and even options like early check-in or late checkout. Easy, convenient, and all at your fingertips.brbrCANCELLATION POLICYbrWe understand that plans can change unexpectedly, which is why we have a flexible cancellation policy in place. If you cancel your booking more than 14 days before your scheduled arrival date, you will receive a full refund of the total booking amount. If you cancel more than 7 days before arrival, you will receive a 50% refund. Unfortunately, cancellations made within 7 days of arrival are non-refundable. However, we will do our best to accommodate any change requests, subject to availability and applicable fees.brbrCLEANING FEEbrOur cleaning fee is designed to ensure transparency and support our dedicated cleaning team, who are compensated with living wages to maintain high standards of cleanliness and service throughout your stay. This fee also includes a unique damage protection policy, providing peace of mind during your visit. It’s not a profit-driven charge, but one that helps maintain the quality of your experience. Guests often praise our attention to cleanliness, and we’re committed to making sure every detail of your stay is perfect. We're always available to promptly address any concerns, ensuring you can relax and enjoy your time in our home.brbrYour perfect Getaway & Stay awaits—can't wait to host you!
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Sleep 4

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Exceptional(68)

$1789.8

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Condo

101 | Luxury | Downtown Sister Bay

Sister Bay, Wisconsin, United States

Please follow on “Instagram” “@101sisterbay” for virtual tour.brbr101 is a seventeen-hundred square foot, three-bedroom, vacation rental located in downtown Sister Bay directly across from the marina. brbrWalk to everything Sister Bay has to offer! brAfter pulling up and utilizing 101’s coveted downtown parking spot and garage, you will walk through the private entrance and be amazed. Every detail has been thought of in this luxury condominium.brbrFully equipped kitchen includes custom cabinetry, quartz countertops, stainless steel GE cafe appliances, premium lighting, decorative tile, wet bar, counter seating, and more. Make yourself a latte on the DeLonghi espresso machine at the coffee bar, sit out on your private patio, and take in the beautiful views.brbrLiving room has a giant marina viewing window, access to the patio, coffered ceilings, and a thin LG OLED television mounted above the gas fireplace. Relax on the comfortable sofa, play board games, do a puzzle or get some work done on the 17th century desk.brbrAfter spending the day exploring the beach, shops and restaurants, watch the sunset from the private patio, while listening to live music from Boathouse on the Bay. brbrIn the evening, retire to the master suite through a sliding barn door and relax on your luxury pillow top mattress. Lift your head up with the Serenade comfort base to make reading or watching tv more comfortable.brbrAll beds have Standard Textile Hotel Luxury sheets, 1200 count down duvets, and touches from our favorite Door County shops, like Jack and Joie and Sister Golden.brbrAll bedrooms are equipped with a flat-screen tvs, cable, and Rokus. Log-in to your Hulu, Netflix, Amazon accounts and enjoy your favorite programming. brbrCondo is fully stocked with everything you need to have a great Door County vacation. Yard games, beach towels, coolers, beach chairs, blankets, volleyballs, tennis equipment. You name it, we’ve thought of it. brbrThis rental puts you right in the heart of Sister Bay, but also allows you to hop in your car and explore other parts of Door County. 5-miles to Ellison Bay and Ephraim, 10-miles to Bailey’s Harbor and Fish Creek, and 15-miles to the Washington Island ferry. brbrDogs are not only welcome but encouraged. *Two dogs maximum. Total weight of both dogs must be under 50 lbs. No Rottweilers or Pit Bulls. While we love all dogs, we must abide and respect condominium rules. All dogs must be approved within 5 days of check-in and a dog agreement must be signed. Pet fee of $50 will apply for breeds whose shedding requires extra cleaning. brbrPlease message us ahead of time if there is anything that can be provided to make your stay more comfortable. We will do our best to provide what you need.brbr2-night minimum in winter and early springbrbr3-night minimum Memorial Day weekend, Labor Day weekend, Fallfest, Thanksgiving, Christmas, New Years, the first half of June and the fall season. brbr7-night minimum in summer. brbrMonthly and seasonal rental also available.brbrComplimentary basic party planning available (bachelor/bachelorette, birthday, anniversary, etc.). For more complex events, we are happy to connect you to several local party planners who can help bring your vision to life.brbrWINTER GUESTS: Garage parking! We are the only lodging in Door County to offer kicksledding for guest use. In addition, snow shoes (6 adult/4 children), sleds (4 double), snowman building kit, and lots of unique games and puzzles are all provided. Please direct message for 2-night minimums in winter!brbrDCTZC permit number: 34-53-2150-00u
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Exceptional(83)

$825.07

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Private Vacation Home

Modern Dörr, Retreat Downtown Sister Bay

Sister Bay, Wisconsin, United States

Downtown Sister Bay, 5 minute walk to beach. Tucked away in an unbeatable location, this gorgeous cottage is just steps from downtown Sister Bay and waterfront! brbrModern Dörr is located on a tranquil wooded lot offering wonderful privacy and natural beauty. Walk to the beach, marina, and Sister Bay’s many fine shops, restaurants and coffee bars. Or choose to stay in and relax with a woodland view on the spacious backyard patio. The outdoor space also serves as a great place to gather with friends and family around the campfire. Step inside and the Scandinavian modern decor and open concept floor plan offers great flexibility and ideal entertaining space for your Door County getaway.brbrGuests will enjoy modern and updated furnishings throughout for 2026 season.brbrModern Dörr is the perfect centralized location to explore the Door County Peninsula. br___________br• 4 mi to Ephraim--Isely Coffee * Wilsons * Chefs Hat * Pearl Wine Bar * Bad Moravian br• 5 mi to Ellison Bay--Island Cider Company * Newport State Park * Mink River * Blue Bear * Della Portabr• 9 mi to Baileys Harbor-- DC Brewing * Sway Brewing * Inland Pizza * Stones Throw Winery br• 9 mi to Fish Creek--Peninsula State Park * Blue Horse * Bayside Tavern * White Gull Innbr• 15 mi to Egg Harbor-- Hatch Distillery * One Barrel Brewing * Pizza Bros * Macready Artisan Bread Co * Fika Bakerybr___________brbr4 cruiser bikes, paddle board, & a kayak available for guests use brbrGas Webber Grill on patio -- Fire Pit w/Chairs -- Many Indoor/Outdoor Gamesbr___________brbr3 night minimum Shoulder season * May 21st - Jun 18th & Aug 30th - Oct 13th * 4 night minimum Fall Fest Weekend. brbr6 night minimum Peak Season with check in at 4pm and and check out at 10am. Jun 26th - Aug 31st. br___________brOutdoor security cameras are placed outside the home for the safety of the guests & home
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Exceptional(36)

$1339.66

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Lodge

Stunning home in Sister Bay- Dog Friendly with fenced in yard!

Sister Bay, Wisconsin, United States

Welcome to King's Landing, hosted by Simple Life Rentals! We invite you, your family, friends, and dogs to stay in this renovated home with a fully fenced-in backyard. We fell in love with this property located in the heart of Sister Bay and put a ton of work into it to make it the ultimate hang-out home. We are honored for you to experience the utmost in comfort and quality time.brbrThis 4-bedroom, 4 bathroom home is four levels and includes a fully stocked kitchen and two separate living spaces. The upstairs bedrooms provide quiet, comfortable rooms to rest and relax, including a bunk room at the very top level in the finished attic. Put the kids to bed and head on downstairs where you will find the finished basement. The basement includes an electronic dart board, pool table, large smart TV, wet bar, and mini fridge. The huge, private backyard features a deck, fire pit, and space to play in the grass.brbrThe home is located along desirable Bay Shore Drive, a short walk to downtown Sister Bay where you can enjoy the beautiful waterfront, beach, and many wonderful restaurants.brbrYour well-behaved dogs are allowed. This property has a fenced-in backyard and allows up to 4 dogs. There is an additional fee collected at booking.brbrProperty Features:br+ Downtown Sister Baybr+ Fully fenced in yardbr+ Dog friendly - 4 maximum dogs per stay br+ Wi-Fi (due to the rural nature of the property, Wi-Fi and cell phone coverage and service can vary) br+ 2 Smart TVs (in each living room) with streaming devices. Guests may log in using their own accounts.br+ Central A/C and Heatbr+ Gas fireplacebr+ Basement includes a second living space, large wet bar, mini-fridge and seating for 6br+ Pool table, commercial dart board with darts, and games for guest’s enjoymentbr+ Bikes and a tandem bike are providedbr+ Fully equipped kitchen (see amenities) including an ice maker and wine fridgebrbrOutdoor Space:br+ Firepit (please bring local firewood)br+ Outdoor seating for up to 12br+ Deck with seating for 6br+ Gas grill with propane providedbrbrSleeping Accommodations:brBedroom 1 (main level): King bed and room darkening shadesbrBedroom 2 (second floor): Queen bed, ceiling fan and room darkening shadesbrBedroom 3 (finished attic): 4 Twin bedsbrBedroom 4 (second floor, above garage, has mini split heating unit): 2 Twin beds and a Queen bedbrbrBathrooms:brBathroom 1 (main level): Full bathroom ensuite with jetted tub and separate walk-in shower brBathroom 2 (second floor): Full bathroom with tub shower combobrBathroom 3 (finished attic): Full bathroom with shower brBathroom 4 (basement): Full bathroom with showerbrbrParking:brThere are spots for 2 cars in the garage and a maximum rule of 4 cars in the driveway. This is strictly enforced by the Village of Sister Bay. brbrAmenity + damage protection waiver includes:br-Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels) br-A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom. br-PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).brbrHome Truths:br**This home bedroom count has been reduced from 5 to 4 due to a Village of Sister Bay restriction**brbrSecurity (Ring) camera located by front door facing the driveway.brbrThis home is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors, we cannot accommodate parties at the property including bachelor or bachelorette parties, reunions, or other rowdy gatherings.brbrDoor County Tourism Zone Commission Permit #34-56-1602-07brbrPlease be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.
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Exceptional(19)

$1153.71

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Private Vacation Home

Renovated Home with Retro Charm and proximity to Downtown Sister Bay

Sister Bay, Wisconsin, United States

Welcome to High Garden, hosted by Simple Life Rentals! A Door County family home for generations, this one-story house was completely renovated in 2017. The spacious kitchen is fully modernized with stainless-steel appliances and a stone countertop for a wonderful space to prepare meals. The nearby dining room comfortably seats 8. The living room boasts a large sectional couch perfect for watching a movie on the 50″ LED HD TV or getting cozy with your laptop, tablet, or smartphone. The master bedroom has a king-size bed, 42″ LED HD TV, and an ensuite bathroom. The shower has a low entry threshold making it easy to get in and out. The 2nd and 3rd bedrooms spaciously accommodate queens and LED TVs. brbrThis property allows up to 3 well-behaved dogs. There is an additional fee collected at booking.brbrProperty Features:br+ Dog friendly - 3 maximum dogsbr+ Fenced-in yardbr+ 4 LED HD Smart TV's (located in living room and each bedroom)br+ Fire pitbr+ Downtown Sister Baybr+ Central A/C and Heatbr+ Wi-Fi (due to the rural nature of the property, Wi-Fi and cell phone coverage and service can vary)brbrSleeping Accommodations:brBedroom 1 (main level): King size bed, TV, and ensuite bathroom with stand-up shower. brBedroom 2 (main level): Queen bed and TV brBedroom 3 (main level): Queen bed and TVbrbrBathrooms:brBathroom 1 (main level): Full bathroom with shower onlybrBathroom 2 (main level): Full bathroom with shower tub combobrbrOutdoor Space:brDeck includes seating for 6brFirepit with 6 chairs (please bring local firewood)brGas grill with propane providedbrFenced-in backyardbrbrParking:brParking available for 2 cars.brbrAmenity + damage protection waiver includes:br-Bed linens, pillows, blankets, and bathroom towels. (Please bring your own beach towels) br-A starter pack of essentials which includes toilet paper, paper towel, dish soap, dishwasher soap, hand soap, and garbage bags. Due to septic systems, we do not provide facial tissue. One each of travel size shampoo, conditioner, and body wash per full bathroom. br-PEACE OF MIND Damage protection covers up to $1000 per stay for accidental damage that is reported prior to departure (excludes any pet damage).brbrHome Truths:brFireplace is not for guest usebrbrThis property is located in a quiet community with neighbors and is geared towards quiet family vacations. Due to the proximity of neighbors and municipal restrictions, we cannot accommodate parties at the property including bachelor or bachelorette parties, reunions, weddings, or other gatherings.brbrDoor County Tourism Zone Commission Permit #34-56-1888-07brbrPlease be aware that you must sign a terms and conditions agreement, which will be sent to you separately, to finalize your reservation.
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Exceptional(26)

$296.38

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Cottage

Charming Cottage On The Shore Of Lake Michigan!

Sister Bay, Wisconsin, United States

2019 Update: Over the winter work was done int the crawl space to address the musty smell. We are also providing a dehumidifier for those damp, chilly days. The master bedroom has been completely renovated.brbr2 Bedrooms, 1 Bathroom, Sleeps 6brAppleport Sunrise is a charming, cozy, and comfortably furnished two-bedroom, one-bath seasonal cottage on the rocky shore (bring your beach shoes) of Lake Michigan that affords spectacular views and a quiet retreat. Located at 10372 South Appleport Lane, just a few minutes east of Sister Bay, and on Rowley’s Bay, the cabin’s open floor plan (kitchen-dining-great room) also features a deck overlooking the lake, a stone mantel gas fireplace, and ceiling fan. The kitchen is fully equipped with electric stove, refrigerator, and microwave. The great room provides internet, DVD player, games, and puzzles.brThe master bedroom has a king bed. The guest bedroom has a bunk bed with a full size bed on bottom, twin bed on top and a twin trundle. The bathroom has a standup shower.brA charcoal grill can be found on the concrete patio outside the kitchen. The fire pit overlooking the lake is the perfect place for grilling hot dogs and marshmallows, or warming up on chilly evenings.brbr*Cannot be turned over during peak season*brbr** No Camper or Boat parking at any time. Contact the local township for information on public overnight parking **brbrAccommodationsbrFully stocked kitchen, microwave, toaster, coffee makerbrLarge deckbrCharcoal grillbr37 Flat-screen TV (no cable)brInternetbrDVD playerbrCeiling fan (family room & guest bedroom)brOther fans (3)br3 electric heatersbrStone- gas fireplace brFire pit brWasher & dryerbr
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