Vacation Rentals By Owner In Sheboygan, WI

$372.28

Lovely Lake Lookout - Cozy 2BR Condo Steps from Lake Michigan

Sheboygan, Wisconsin, United States

Welcome to Lovely Lake Lookout — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrUnwind at this cozy 2BR/2BA condo just moments from Lake Michigan. Enjoy evenings by the gas fireplace, dine al fresco on the private patio, and explore nearby shops and restaurants. Fully stocked kitchen, comfy spaces, and local tips for watersport adventures. Managed with care by a local team—no waterpark access, but so much more to love. Your lakeside escape starts here!brbrWelcome to your lakeside escape in the heart of Sheboygan’s South Pier neighborhood—just steps from the sandy shores of Lake Michigan. This stylish 2-bedroom, 2-bath villa is located on the main level with no stairs, offering easy access and a comfortable layout for all guests.brbrThe master suite boasts a king-size bed, smart TV, charging station, and a private bathroom. The second bedroom features a queen bed and a full-size over twin bunk bed, suitable for adults, with a smart TV and ample storage. For additional sleeping space, a pull-out sofa sleeper awaits in the living room. Enjoy a blend of relaxation and functionality in this well-appointed condo during your stay.brbr ’ :br✔ Stunning lake views from your private patiobr✔ Two well-appointed bedrooms and two full bathroomsbr✔ Cozy gas fireplace—perfect for relaxing eveningsbr✔ Fully equipped kitchen with modern appliancesbr✔ Complimentary coffee bar to start your mornings rightbr✔ Comfortable living spaces designed for connection and restbr✔ Keyless entry for seamless self check-inbr✔ Walkable to public beaches, dining, and local attractionsbrbrYou'll have the entire villa to yourself—private, peaceful, and thoughtfully designed for both relaxation and adventure. Whether you're here to unwind or explore, this is your perfect home base in Sheboygan.brbr :br* Deland Park — 0.2 milesbrEnjoy beach access, picnic spots, playgrounds, and the historic Lottie Cooper Shipwreck display. Popular for surfing and seasonal kite festivals.br* Sheboygan Marina — 0.3 milesbrOffers boat rentals, fishing, and scenic Lake Michigan views.br* North Point Park — 0.5 milesbrA peaceful park with picturesque lake views and walking trails.br* John Michael Kohler Arts Center — 1 milebrContemporary art exhibitions, interactive installations, and live performances.br* Above and Beyond Children’s Museum — 1 milebrFun, educational exhibits perfect for family visits.brbr & :br* Lino Ristorante Italiano — 0.4 milesbrUpscale Italian dining with authentic dishes and elegant ambiance.br* Weather Center Café — 0.3 milesbrCozy café specializing in specialty coffee, teas, and light meals.br* Field to Fork — 0.9 milesbrFresh, locally sourced meals with a bakery and coffee roastery — great for breakfast or lunch.brbr & :br* Sheboygan Farmers Market — 0.9 miles (Fountain Park)brWednesdays and Saturdays (June–October) with fresh produce, crafts, and live entertainment.br* Deland Park Kite Festival — 0.2 milesbrAnnual family-friendly event with vibrant kite displays.br* Sheboygan Midwest Challenge — 0.5 miles (near Sheboygan Yacht Club)brAugust powerboat racing event drawing crowds for thrilling high-speed races.brbr : br- This condo is privately owned and does not include access to the Blue Harbor Resort water park. Guests may not purchase day passes, as the unit owner has waived the Resort Amenity Fee.br- Renters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.brbrWe are excited to host you! Your satisfaction and comfort are our top priorities. Book now and experience lakeside living at its finest! Your Perfect Getaway Awaits!

2

Bed

2

Bath

8

Sleeps

$254.72

/ Nightly

Private Vacation Home

Coastal Comfort & Golfers' Paradise in Sheboygan!

Sheboygan, Wisconsin, United States

Nestled in the heart of the Historic District of Sheboygan, this 3-bedroom, 2-bathroom home is your basecamp for Lake Michigan and world-class golf. Catch a sunrise at the beach or tackle the greens at Whistling Straits — everything is within reach. Whether you’re here for a weekend of legendary fairways or just to enjoy the fresh lake air, this retreat puts the best of the city right at your doorstep. Grab your clubs and see why Sheboygan is the ultimate lakeside escape!brbr-- THE PROPERTY --brbr- Primary Suite: Features a comfortable king-sized bedbr- Guest Rooms: Two additional bedrooms each feature a queen-sized bedbr- Fully Equipped: Full kitchen, in-home washer/dryer, high-speed Wi-Fi, and a Smart TVbr- Entertainment: Unwind with tons of board games for a cozy night inbr- Total Comfort: Climate-controlled with AC and central heatingbr- Parking: Private driveway for easy, off-street parkingbr- Grill: Fire up the outdoor grill for a post-golf BBQbrbr-- THE LOCATION --brbr- Walkable: A short stroll to the Lake, and restaurants and shops of downtown Sheboyganbr- World-class golf is waiting at Whistling Straits, Black Wolf Run, and others, all nearby!brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Dog friendly w/ $50 fee (+ taxes & fees, max 2)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires exterior uneven stairs to enter (with a handrail on 1 side) and an additional interior staircase to access all bedrooms on the 2nd floor

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Select Dates for Price

Private Vacation Home

Riverfront Sheboygan Townhome w/ Grill!

Sheboygan, Wisconsin, United States

Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. This 2-story Sheboygan vacation rental is the perfect place to spend time on the water, with on-site river access and proximity to beaches lining the shores of the lake close by. Take the kayak and paddleboard out for a peaceful ride, stroll the boardwalk through the sand dunes and golden beach of Kohler-Andrae State Park, or walk downtown to explore the museums and nightlife.brbr-- THE PROPERTY --brbrFurnished Balcony | Gas Grill | Kayak & Paddle Board | 1,200 Sq FtbrbrBedroom 1: King Bed | Bedroom 2: King Bed, Queen Murphy Bed | Living Room: Sleeper Sofa | Additional Sleeping: Queen Air Mattress, Pack ‘n PlaybrbrINDOOR LIVING: Smart TVs w/ cable, Amazon Alexa, board games, breakfast bar w/ seatingbrOUTDOOR LIVING: Bicycles w/ helmets, beach chairs, beach towels & blanket, beach cart, cooler, outdoor gamesbrBABY SUPPLIES: High chair, bath seat, swing, sound machinesbrKITCHEN: Cooking basics, cooking spices, dishware/flatware, dishwasher, refrigerator, stove, microwave, cooler, coffee maker, K-cups, tea, blender, Instant Pot, air fryer, toaster, ice maker, garbage disposalbrGENERAL: Free WiFi (500 Mbps), keyless entry, central heating & air conditioning, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, clothes steamer, iron/board, hangers, hair dryer, hair straightener, sharps container, trash bags/paper towelsbrSUITABILITY: Stairs required for access, 2-story townhomebrPARKING: Street parking (first-come, first-served)brbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Kiwanis Park (0.7 miles), Bookworm Gardens (2.7 miles), Maywood (3.3 miles), Kohler-Andrae State Park (6.7 miles), Whistling Straits Golf Course (6.9 miles)brON THE WATER: River access (on-site), Deland Park (1.4 miles), Harbor Centre Marina (1.5 miles), Blue Harbor Resort & Water Park (1.5 miles), South Shore Beach (1.8 miles)brNEARBY FUN: Above & Beyond Children's Museum (0.9 miles), John Michael Kohler Arts Center (1.0 miles), Kohler Design Center (4.4 miles), Odyssey Fun Center (5.8 miles), Elkhart Lake's Road America (16.9 miles) brAIRPORT: General Mitchell International Airport (65.9 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to access

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Sleeps

$212.18

/ Nightly

Apartment

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Sheboygan, Wisconsin, United States

About this space:brRenovated 1930's home located in the historic downtown district within walking distance of breathtaking views of Lake Michigan, trails, parks, shopping, dining, Kohler Art Museum, Children's Museum and more! You will enjoy the 1200 square foot, two bedroom renovated upper unit of this historic home. Great care was taken to keep the old world charm. We know you will enjoy our Blast from the Past as you play records, tapes, and cd's. Send inquiry on big discounts on stays ore than 2 days!brbrThe space:brOur home boasts a boiler heat systembrThe major benefit to the traveler is that it's much less drying during winter months. We also include a one car garage with opener and keypad. Electronic locks for super easy access also!brbrGuest access:brYou will have access to entire upstairs apartment including upper deck, one car garage, and washer/dryer in the basement.brbrOther things to note:brDogs are okay with an additional one-time $100 fee and advance notice. No cats please.

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Sleeps

$595.88

/ Nightly

Private Vacation Home

4- Bedroom Retreat with Sauna, Game Room, Patio & Walk to Bars & Restaurants

Sheboygan, Wisconsin, United States

This newly renovated home offers the ultimate blend of comfort, fun, and convenience. Located in the heart of the city, you’ll be just steps away from the area’s best restaurants, bars, coffee shops, and nightlife. brbrInside, enjoy a spacious area ideal for relaxing or entertaining. Each bedroom has its own smart TV. Challenge your friends or family in the fully equipped game room, featuring a pool table, air hockey, and more. After a day exploring the city, unwind in your private 2 person sauna.brbrbrStep outdoor to enjoy a spacious 20 foot gazebo with dinning room seating and a sectional couch, a charcoal grill for outdoor cooking and a brand new fire pit with cozy seating- perfect for summer nights. But that’s not all: the backyard offers direct access to a park with a basketball court, giving kids even more to love.

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$378.83

/ Nightly

Private Vacation Home

BEACHVIEW GETAWAY

Sheboygan, Wisconsin, United States

Amazing location just off of Lake Michigan. A quick walk to the public beach across the street or downtown as well. Previous owner was an architect and owned the home for 60 years before he decided to downsize. Over 2200 square feet of living space. All FIVE bedrooms and a full bath are upstairs. There is a half bath on the main floor. The full bath upstairs has a stand-alone shower and a new whirlpool tub. Three bedrooms have queen size beds and TV's. Two smaller bedrooms each have a twin size bed. A queen size air mattress can be set up in on the first floor when needed with prior notice. There is a laundry room just off of the kitchen. There is a half bath on the main floor.brPlenty of room for the whole family. Perfect for a golfing weekend., family trip or girls' weekend. There is a gas grill out back. No smoking is allowed in the house. No parties or events are allowed on the property. Due to allergies, no pets are allowed. Minutes away from shopping and several golf courses around town. The interior of the home has just been repainted and new flooring put in. There is a 65 TV in the living room. WIFI access and cable TV present. Plenty of street parking along with a large two car garage at the back of the property. Check in time is 4pm or later and check out time is by 10am. There is a keypad on the front door for easy check in. I will provide the code two days before your arrival.

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Sleeps

$401.79

/ Nightly

Private Vacation Home

New King Park Beach Lookout Deluxe! 3BR Right at Lake!

Sheboygan, Wisconsin, United States

Welcome to King Park Beach Lookout Deluxe!brbrExperience the perfect family getaway with panoramic views of Lake Michigan, where comfort and convenience meet. The property is on a large corner lot directly across from a beautiful public beach and playground, offering unbeatable beach access and opportunities for sunrise walks. The open-concept living, dining, and kitchen areas feature expansive windows, keeping you connected to the lake throughout the day, regardless of season or weather. A favorite feature is the finished garage space that offers amenities such as a TV, a foosball table, a dining table, furnishings, and a mosquito net entrance. This space acts as a three-season room with great lake views and creates an ideal setting for family play, relaxation, or movie nights (Available May 1- October 31).brbrThis home features two bathrooms, two main-level bedrooms, and a spacious upstairs bunk room, perfect for guests of all ages with room for sleepovers, games, or simply hanging out. The fully equipped kitchen includes modern appliances and ample counter space, ideal for preparing meals or enjoying takeout. The dining table offers stunning lake views, while the sofa table provides additional seating. For comfort, the home offers central air with an extra room air conditioner to keep the upstairs cool. Enjoy high-speed internet and LIVE TV with Roku in the living area, king bedroom, and upstairs bunk room. Off-street parking plus a full-sized washer and dryer in the basement are available for guest use.brbrThe Beach Lookout Deluxe is the perfect starting point for exploring a variety of local attractions. Just a short distance away, you'll find the South Pier, charming downtown Sheboygan with its unique shops and restaurants, and the scenic village of Kohler. Whether you're teeing off at world-class golf courses, unwinding at the luxurious Kohler water spa, or heading to Elkhart Lake for thrilling racing at Road America, there's something for everyone. Outdoor enthusiasts will love the nearby waterfront, offering opportunities for charter fishing, kayaking, sailing, kiteboarding, and some of the best surfing in the Midwest. For a peaceful retreat, visit Kohler-Andrea State Park to explore sand dunes and marshlands. Don’t compromise between lake views and proximity to the beach, have it all at the Beach Lookout Deluxe. Reserve your dates now and start planning your perfect escape!br

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Bath

Sleeps

$496.0

/ Nightly

Private Vacation Home

LUXE Manor with Modern, Elegant Vibes

Sheboygan, Wisconsin, United States

Modern chic blends with classic sophistication in this late 1800s Manor. Enjoy the expansive 4,500 square feet of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertainment throughout, plus a designer patio. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown. Just a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.brbrTravel Time:br50 minutes to Milwaukeebr60 minutes to Green Baybr15 minutes to Whistling Straightsbr20 minutes to Elkhart Lakebr10 minutes to Kohler Water Spabr2 minutes from the Lakefrontbr2 minutes from Downtown SheboyganbrbrWelcome to the Wayne Charles Manor.brThe modern touches and stylish furniture throughout each room complement the original character of the manor which has been preserved throughout the years. The home features two wood-burning fireplaces, one in the great room and another in the den; nicknamed the green room. The great room also boasts an expansive wall of windows overlooking the manicured yard with a patio area and a garden pond which is frequented by mallards.brbrEnjoy every detail of the fine craftsmanship; stained glass windows, hardwood floors, original light fixtures, crown molding, and rich woodwork.brbrThe parlor features a baby grand piano and soaks in the sunlight almost all day long. Enjoy a formal dinner in the dining room featuring a built-in bar, rich woodwork, and stained glass windows.brbrThe eat-in kitchen is full of sunshine and is the perfect place to cook an evening dinner or enjoy a morning cup of coffee.brbrPatio season is everything and the bar is set high! Despite being located just a few minutes from Downtown and the lakefront, the Manor sits on a lot of just over half an acre. Mature trees, a garden pond, a grilling area, a designer patio, and a beautifully manicured lawn add to the charm of this mini-mansion. You are guaranteed to see an array of bird species, mallards, and rabbits! Firewood is provided should you want to have an outdoor fire.br

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$315.17

/ Nightly

Condo

BEACHSIDE GETAWAY IN SHEBOYGAN

Sheboygan, Wisconsin, United States

Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4 unit building. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features granite countertops, stainless steel appliances, maple cabinetry and front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.brAll the adjacent beaches are public so you have easy access. Located less than a mile from downtown Sheboygan and in close proximity to all the golf courses around town. There is one television in the living room with Roku and basic cable. Each bedroom has a TV as well. There is Wi-Fi. There is a queen size mattress in each bedroom. There are ceiling fans in the bedrooms and the living room. One bedroom has a wall mounted air conditioning unit and the other has a portable air conditioning unit. There is a one car detached garage just off the balcony and street parking as well. Opposite side parking rules exist during the winter months only. There is a one car garage. There is also a parking space on the west side of the building, that if open, you are allowed to use.

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Bath

Sleeps

$945.83

/ Nightly

Private Vacation Home

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

Sheboygan, Wisconsin, United States

Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you the ultimate in privacy & serenity. Enjoy the view year-round from the 4-season sunroom. There are two 1st floor BRs. Upper primary suite offering a walk-in shower, fireplace, huge walk-in closet & patio doors to large upper deck with magnificent lake views! 2 car garage. Sunrises over Lake Michigan & sunsets over the Black River. Currently, there is no direct access to the water.

4

Bed

2

Bath

12

Sleeps

$383.57

/ Nightly

Private Vacation Home

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan, Wisconsin, United States

Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan and an easy stroll to all that the downtown has to offer. brbrWe have 3 bedrooms with plenty of room to spread out. We are a sucker for a good theme so in the two downstairs bedrooms you will find small nods to our love for golf and cheese. One bathroom and laundry located on the main floor. Upstairs you will find another bedroom/loft and private bathroom. There is also a desk and kids corner where we hope they will have hours of fun. brbrOther Features: br- Fully equipped kitchen with modern appliances for all your cooking needs. - - Staples like salt& pepper, oil and basic seasonings provided. br-Keurig and Regular coffee pot with fully stocked coffee bar. Even a small coffee pot in the upstairs bedroom perfect for those lazy morningsbr-Gas fireplace br-Bottomless popcorn for movie nights br- Wi-Fi and Smart TV's giving you access to all your favorite streaming channelsbr-Spacious private backyard. br-Board Games, puzzles and books sure to entertain for hours br- Pack & Play, High Chair, kids plates/bowls/cups, baby gate at the top of the stairs, Kids Toys br- Grill and Outdoor Seating br- Lawn Games & Foosball Table br- Beach Towels, Chair, Toys and Cooler provided br-15 minute drive to Whistling Straights and Black Wolf Run br-20 minute drive to Kohler-Andrae State Park br-Many parks within walking distance (including historic Deland Park)br-Farmers Market every Saturday in the warmer months. Within a 1 minute walk from the house br-Easy walk to downtown shops and restaurants

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Sleeps

$291.52

/ Nightly

Private Vacation Home

Pet-Friendly 3BR Retreat!

Sheboygan, Wisconsin, United States

Relaxing 3-Bedroom Retreat Near Lake Michigan – Pet Friendly!brbrWelcome to your perfect home base in Sheboygan! This spacious 3-bedroom, 1-sofa bed, 1-bath, and basement with laundry, some weights, and pool table to offer comfort and convenience for your next getaway. Enjoy a full kitchen, a pool table for some fun, and the ease of having your own washer and dryer during your stay.brbrStep outside to a fully fenced backyard — great for pets — and fire up the Weber grill for a backyard BBQ.brbrYou’ll be just 5 miles from beautiful Lake Michigan and only 25 minutes from the excitement of Road America. Love the outdoors Explore nearby hiking spots like Kohler-Andrae State Park and the Ice Age Trail.brbrGolfers and spa-goers will love being close to Destination Kohler, home to Whistling Straits, Blackwolf Run, and the luxurious Kohler Waters Spa.brbrLocated halfway between Milwaukee and Green Bay, you’re in the perfect spot to explore everything the area has to offer.brbrAnd don’t miss some of my favorite local spots — grab breakfast or lunch at Field to Fork, or enjoy an evening out at Urbane Restaurant and Cocktail Bar on 8th Street in downtown Sheboygan.brbrWe’d love to host you — come relax, explore, and feel right at home!

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$911.38

/ Nightly

Private Vacation Home

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

Sheboygan, Wisconsin, United States

Escape to Sheboygan Chalet—a stunning modern retreat tucked in the woods of the Black River community Just two blocks from Lake Michigan and a short walk to Majerle’s Supper Club, this home blends style, comfort, and endless entertainment.brbrHighlights include:brbr4 spacious bedrooms, sleeps 10+brChef’s kitchen with quartz island ️brHot tub, infrared sauna & fire table brEpic game room with arcades, PS5 & ping pong brPeaceful wooded views from two decksbrbrThe perfect year-round getaway!brbrWelcome to Sheboygan Chalet | Game Room • Hot Tub • Sauna • Walk to Supper Club & LakebrbrWhether you`re planning a cozy fall retreat , a snowy winter weekend ❄️, or a summer adventure by the lake , Sheboygan Chalet offers the perfect year-round escape in one of Wisconsin’s most sought-after neighborhoods—Black River. Recently renovated from top to bottom, this peaceful wooded home is just two blocks from Lake Michigan and a short stroll to Majerle’s, a classic Wisconsin supper club . Designed with comfort, entertainment, and style in mind, Sheboygan Chalet is ideal for families, friends, and memory-making getaways.brbrbrbrBedrooms & Sleeping Arrangements ️brbrThis home offers three levels of space, comfortably sleeping up to 12 guests:brbrPrimary Bedroom (Upper Level): King bed, ensuite bathroom with a relaxing steam shower , and private access to a bonus bedroombrbrBonus Bedroom (Upper Level): Three twin beds – perfect for kids brbrBedroom 2 (Upper Level): Queen-over-Queen bunk bed with shared full hallway bathroombrbrBedroom 3 (Main Level): Queen bed with adjacent full bathroombrbrLower Level Rec Room: Queen pull-out couch for flexible sleeping space ️brbrFresh linens and cozy bedding are provided throughout.brbrbrbrbrKitchen, Dining & Living Spaces ️brbrThe open-concept layout is filled with natural light thanks to cathedral ceilings, skylights, and expansive windows overlooking the pines brbrFully equipped chef’s kitchen with quartz island, stainless steel appliances, and everything you need to cookbrbrDining room with access to one of two large decksbrbrLiving room with forest views, perfect for gathering or relaxingbrbrbrbrbrEntertainment for All Ages brbrThere`s something for everyone at Sheboygan Chalet:brbrGame Room (converted 32x24 garage):brbrMotorcycle racing arcade machines ️brbrKids climbing walls brbrPing pong table brbrCard table with games ♠️brbrPlayStation 5 with Smart TV brbrLower-level lounge with bar and chill-out space brbrHigh-speed WiFi and smart TVs for streaming brbrbrbrbrOutdoor Amenities brbrUnwind and enjoy the natural beauty that surrounds the home:brbrHot tub with peaceful forest backdrop brbrInfrared sauna for spa-like relaxation brbrFire table for evening conversations and s’mores brbrTwo expansive decks for lounging or diningbrbrWeber Genesis propane grill for outdoor cooking brbrbrbrbrLocation Highlights brbrLocated in Sheboygan`s tranquil Black River community, the home is close to everything while feeling worlds away:brbrTwo blocks from Lake Michigan access brbrShort walk to Majerle’s Supper Club for cocktails and classic Wisconsin fare brbr10 minutes to downtown Sheboygan, the marina, beach, and shops ️brbrNearby hiking trails, golf courses, and year-round recreation ‍♂️ ️brbrbrbrbrGuest Experience ✨brbrAt Sheboygan Chalet, we’ve thought through every detail so you can focus on making memories. From early morning coffee on the deck ☕ to late-night arcade competitions and everything in between, this home offers the perfect blend of relaxation and fun. Our team is committed to cleanliness, comfort, and top-tier hospitality throughout your stay.brbrbrbrbr Elevate Your Stay with VIP ExperiencesbrbrWisconsin Getaways offers exclusive concierge services to make your trip unforgettable:br- Private chefs for in-home gourmet dining.br- On-site massage therapists for ultimate relaxation.br- Custom-curated experiences for your group.brbrYour escape to the woods, the lake, and everything in between starts here. Book your stay at Sheboygan Chalet today and experience the best of Wisconsin’s hidden gem brbr Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limitsbr Maintain respectful noise levelsbr No external speakers or outdoor music of any kindbr No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 4 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.brbrIn alignment with our ongoing commitment to guest safety and comfort, this property has been inspected and approved as a lodging establishment by the Wisconsin Department of Agriculture, Trade and Consumer Protection. brbrFollow @WisconsinGetaways for updates, specials, and new property launches.br Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limits (including visitors)br Maintain respectful noise levels (neighbors should not hear yelling or cursing at any time)br No outdoor speakers or amplified music (leave your speakers at home)br No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 4 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.

3

Bath

13

Sleeps

Exceptional(3)

$810.72

/ Nightly

Private Vacation Home

Central located. Seconds from the highway to get to kohler, and Elkhart lake

Sheboygan, Wisconsin, United States

Everything you need on one level. complete modern Open concept living room, kitchen and dinning area. Hosts two large kitchen islands and bar/tv entertainment area and additional coffee bar. Step out to the Patio and relax with electric concrete fire table. Basement has full bath and additional recreation room. And extra large bedroom.

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Bath

Sleeps

$1031.08

/ Nightly

Private Vacation Home

Modern Lakeside House with Treehouse

Sheboygan, Wisconsin, United States

Welcome to Curtiss Castle! Ideal for large families, remote workers, lake lovers, and golf enthusiasts! This peaceful, woodsy retreat is steps from Lake Michigan. Room enough for the whole family to spread out and relax with a lake breeze!brbrSteps from a semi-private Lake Michigan beachbrbrEnjoy easy access to swimming, sunbathing, and beautiful sunrises without the crowds of a large public beach.brbrExceptional family-friendly amenities including a furnished treehousebrbrKeep guests of all ages entertained with unique features like a treehouse with a gaming console, a PACMAN arcade, and a backyard fire pit.brbrSpacious multi-level home designed for groupsbrbrComfortably accommodate your entire group with multiple living areas, a fully-equipped gourmet kitchen, and an expansive deck for gathering.br brNestled in the highly adored and well-preserved Black River neighborhood of Sheboygan, Wisconsin, near the picturesque shore of Lake Michigan, this home offers the feel of a Northwoods retreat while conveniently located between Green Bay and Milwaukee. This family-friendly home is just steps away from a semi-private beach and mere minutes from Kohler Andrae State Park, Road America, Kohler Waters Spa, and several exceptional golf courses.brbrBEDROOMS & BATHROOMSbrBedding, pillows, towel sets, body wash, hand soap, shampoo, conditioner, and hair dryers are provided.brbrPrimary Bedroom (top floor): King bed with plush topper, hardwood floor, electric fireplace, Smart TV, dresser, expansive walk-in closet with built-in drawers, dressing mirror, portable floor fan, luggage rack, and essential oil diffuser. The ensuite bathroom features Kohler shower fixtures, dual sinks with lighted mirrors, and a toilet with a bidet. brbrGuest Bedroom 1 (top floor): 1 Queen and 1 Twin bed, hardwood floor, 2 closets, open shelves with cube baskets for storage, nightstand, ceiling fan, and dressing mirror.brbrGuest Bedroom 2 (top floor): 1 Queen bed, hardwood floor, chest of drawers, two nightstands with charging ports, desk and chair, portable fan, closet, and dressing mirror. brbrThe guest bathroom on the top floor offers a relaxing soaking bathtub/shower, toilet, and dual sinks. brbrGuest Bedroom 3 (lower level): Two full-size beds with charging ports and LED-lighted shelves in the upholstered headboards, two nightstands and lamps, carpet, recessed lighting, luggage racks, closet, and dressing mirror. brbrThere is a 3/4 bathroom with a shower, toilet, and sink on this level.brbrTwo twin cots are also available in the den area and two pack-n-plays for our youngest guests.brbrMOVIE ROOM/DENbrThe spacious den is perfect for relaxation or family fun with a massive flat-screen TV, powered reclining sofas, electric fireplace, a mini fridge and microwave, cabinets full of board games and family-friendly DVDs, plus a classic PACMAN arcade!brbrKITCHENbrThe gourmet kitchen is equipped with an array of appliances to cater to your cooking and baking needs, including:br-large capacity refrigerator with ice and water dispenser, and a second refrigerator/freezer in the garage so you can stock up on your favorite Wisconsin beverages, cheeses, and frozen custard!br-double ovenbr-dishwasherbr -smooth-top cooking rangebr-air fryerbr-microwavebr-countertop stand mixerbr-spacious pantrybr-pots, pans, dishes, serving ware, & bakewarebr-kids' baking cabinet with cookie cutters and other fun stuffbr-2 high chairsbr-wine and cocktail glasses, coffee mugsbr-Keurig & podsbr-12 cup Brewstation coffeemakerbr-blenderbr-crockpotbr-kettlebr and an assortment of small kitchen gadgetsbr(paper towels, dish soap, dishwasher pods, trash bags, coffee, creamer, sugar, teas, honey, olive oil, and seasonings provided)brbrMAIN LEVEL: SUNROOM/DINING ROOM/LIVING ROOM/EXECUTIVE OFFICE & HALF BATHbrbrAdjacent to the kitchen, the bright and cozy sunroom features a new sofa, heated floors, tall windows, and skylights, providing a perfect spot to unwind. Settle in with a good book and listen to the soothing waves of Lake Michigan while enjoying your morning coffee or watching the graceful deer!brbrFreshly furnished living room with fireplace, sofa, swivel chair, and remote-controlled AC. Local guidebooks are in a basket, and playing cards are in the end table drawers. brbrThere is a large family dining table with seating for 8 and additional bar stool seating for 6 around the granite kitchen island. The cocktail cabinet is stocked with assorted glasses, wine/bottle openers, a cocktail shaker, and wine stoppers. brbrRemote workers will appreciate the private office room, equipped with a desk and rolling chair, monitor, printer with ink, copy paper, sofa, built-in bookcases with books for all ages and interests, and a writing desk.brbrTREEHOUSE/DECK/BACKYARD & BEACH FUNbrbrThe expansive three-tiered deck has plenty of seating and play space, a gas grill, and a fire table with propane provided. There is an inground fire pit in the backyard with complimentary firewood (when available- firewood is not guaranteed).brbrTREEHOUSE- Kids and teens will enjoy hanging out in the furnished treehouse with indoor and outdoor lighting, a kid-size futon, and a Papasan chair. Here, they’ll find more board games, coloring books, a PlayStation 3 with several games, and a tote full of artificial flowers for creating an outdoor fantasy garden.. brbrThere is an infant/toddler swing for our youngest guests. The playground at the end of the street by the fire station has basketball goals, soccer nets, swings, and slides.brbrIn the garage, you'll find an assortment of outdoor toys, including 2 adult Trek bikes, 2 children's bikes, a beach wagon, cooler, and sand toys. Beach towels are located in bins in the foyer. brbrWith ample space for family fun and a serene atmosphere, Curtiss Castle beckons you to spread out and relax. Whether you prefer to indulge in activities near the enchanting Lake Michigan or immerse yourself in the world-class golf courses nearby, this retreat will serve as your home away from home.brbrThis home is privately owned and professionally cleaned before each booking. brThe maximum number of guests is 11, including children and infants. No parties, pets, or additional guests are permitted.brbrSecurity Cameras: There are 3 outdoor security cameras (front door, back door main entrance, and treehouse facing fire pit to monitor fires) and one in the garage to allow us to ensure the garage doors are closed and the bikes are put away. There are no cameras inside the house.

Bed

Bath

Sleeps

$658.71

/ Nightly

Condo

Edgewater Escape: 4 Bedroom, Sleeps 14!

Sheboygan, Wisconsin, United States

This is your new favorite vacation spot. A spacious, two-level condo located just across the courtyard from the beautiful beaches of Lake Michigan. It's the perfect place to relax, recharge, and enjoy quality time with family and friends. You're close to all the action but can always retreat to your peaceful home away from home.brbrPLEASE NOTE: Renters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee. Guests and occupants are not permitted to access or attempt to access Breaker Bay Waterpark. Purchasing or attempting to purchase tickets is strictly prohibited. Violations may result in a fine at the owner’s discretion, which will be the guest’s responsibility and must be paid in full.brbrStep inside to a bright and airy open-concept living area, where large windows fill the space with natural light and create a welcoming atmosphere. The main level is a hub for relaxation and connection, featuring a cozy living room, a dining area for shared meals, and a fully equipped kitchen. From here, you can step out onto your private balcony to enjoy a fresh breeze and views of the peaceful courtyard. The beach and lake are located just across the courtyard, making it a quick walk to the water's edge.brbrThis condo offers ample space for everyone, with four spacious bedrooms spread across two levels. The main floor features two inviting bedrooms, while the upper level holds a special treat: a tranquil master suite complete with a jetted soaking tub in its private bathroom. The upstairs also includes a convenient laundry area, so you can pack light and stay fresh.brbrStarter EssentialsbrWe provide a few essentials to help you settle in comfortably. Guests are responsible for purchasing any additional items they may need during their stay. We do not supply beach chairs or beach towels, so please remember to bring your own.brbrExplore Your SurroundingsbrThe location couldn't be better. You're a short walk from the beach and the scenic lakefront path, and surrounded by Sheboygan's best attractions and eateries.brbrBeach & Parks: Quick drive to Deland Park for beach access, playgrounds, and the historic Lottie Cooper Shipwreck. brbrDining: Enjoy waterfront dining at Parker Johns BBQ & Pizza, upscale fine dining at Harry's Prohibition Bistro, a cozy coffee & croffle at eb flo coffee house, or a sweet treat at South Pier Parlor! All located on the boardwalk right next to the resort, or across the river!brbrFun for All: The John Michael Kohler Arts Center, Above and Beyond Children's Museum, and bookworm gardens offer cultural and educational fun just a short distance away.brbrGood to KnowbrAccessibility: This is a two-story condo. There are stairs to the main living area and a second set of stairs to the upper level.brbrParking: Free on-site parking is available for guests.brbrbrWe can't wait to host you! Book your perfect lakeside getaway today. Once booked, check out the Guidebook for some more local recommendations!brbrRental Agreement Required: A separate rental agreement is required to be signed after booking and can be reviewed in advance upon request. The agreement includes standard terms such as house rules, guest responsibilities, and property-specific policies (for example, rules regarding pool/hot tub use, prohibited access to Breaker Bay Water park, and guest liability for damages).brGuests will receive the agreement electronically after booking and must sign within 48 hours to maintain their reservation. Failure to sign will result in cancellation.

Bed

Bath

Sleeps

$629.7

/ Nightly

Condo

Just Beachy: 4 Bedroom, Sleeps 12!

Sheboygan, Wisconsin, United States

Newly Renovated 4BR/3BA Upper-Level Condo – Walk to Boardwalk, Harbor & More!brbrWelcome to your perfect home away from home! This spacious, two-story 4-bedroom, 3-bathroom upper-level condo has been newly renovated with stylish upgrades throughout, including modern showers, sleek new flooring, and beautiful kitchen backsplashes—giving the space a fresh, clean, and comfortable feel.brbrNestled in a prime location, you're just a short stroll from the boardwalk, harbor, and downtown restaurants—everything you need for a relaxing or adventure-filled stay. Whether you're planning a weekend getaway or an extended vacation, this unit is ideally situated to explore the best of the area.brbrLooking to explore further You're just a 30-minute drive from:brbrWhistling Straits – world-renowned golf destinationbrbrKohler Spa – luxury relaxation and wellnessbrbrRoad America – thrilling motorsport eventsbrbrThis courtyard-facing condo is thoughtfully equipped and perfect for families, couples, or groups of friends. While the unit comfortably sleeps a group, please note that it does not include bunk beds.brbrImportant Note:brWe are a separate company from the Resort, and therefore, Resort amenities are not included with your stay.brbrWhether you’re in town for leisure, events, or just to unwind by the water, this newly updated condo offers comfort, style, and unbeatable access to everything!brbr****Renters and guests of this condominium unit do NOT have access to or use of the Blue Harbor Resort water park and WILL NOT TRY TO PURCHASE a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.****brbrStarter essentials are provided to help you settle in comfortably. This includes 2 rolls of toilet paper per bathroom, 1 paper towel roll, 2 dishwasher pods, a small bottle of dish soap, a sponge, 2 laundry pods, bath towels, fresh linens, and a few garbage bags. Guests are responsible for purchasing any additional items they may need during their stay. Please note: we do not supply beach chairs or beach towels, so guests should bring their own.

4

Bed

3

Bath

12

Sleeps

$659.61

/ Nightly

Condo

Waterfront Sheboygan Condo

Sheboygan, Wisconsin, United States

Welcome to your Lake Michigan, Sheboygan Getaway - riverfront condo sitting right on Sheboygan's riverfront board walk and approx. 5min walk to beautiful south shore public sandy beach, restaurant & shopping in walking distance. brbrThis condo has open-concept, two floors with 3 bedroom, Loft, 2 bath condo combines comfort with Wisconsin riverfront charm - perfect for families, couples, or business travelers seeking a peaceful retreat. Sleeps 12, features 4 queen beds, 1 bunk bed and 1 sofa bed. brbrSheboygan is considered the Freshwater Capital of the World. On the Wisconsin shore of the magnificent Lake Michigan, you can enjoy breathtaking views of the lake and its sunrises, making it the perfect destination for a romantic seaside escape.brbrFull stocked with beach towels and folding chairs to enjoy at the beach. Games, Books and Toys for your enjoyment. Enjoy Internet and Cable TV.brbrWasher and dryer with laundry detergent and dryer sheets are available in loft area laundry room. Bathrooms are stocked with towels, hand soap, shower gel, shampoo and conditioner. brbrKitchen has everything you'll need to cook and dine at home or just heat up leftovers from Sheboygan's amazing restaurants. Kitchen appliances include dishwasher, oven, fridge, coffee makers, and toaster. Dish soap, dishwasher detergent, garbage bags, and paper towels are all provided.brbr :br- Deland Park – Beach access, picnic areas, playgrounds, and annual kite festivals.br- Sheboygan Marina – Boat rentals, fishing, and scenic waterfront views.br- North Point Park – Lake views, walking trails.br- John Michael Kohler Arts Center – Art exhibitions.br- Above and Beyond Children's Museum – Hands-on exhibits and programs for children.br- Harbor Centre Marina – Boat rentals, fishing, and waterfront views.br- South Pier Parlor – Ice cream, mini-golf, and arcade games; popular for families.br- Sheboygan Midwest Challenge (August) - Power boat races and family fun.br- Kohler's 5 star PGA championship golf coursesbr- Kohler Andrae State Park - majestic sand dunes, miles of golden beach, shimmering blue Lake Michigan waterbr- Road America - Motorsport permanent race track, family funbr- Green Bay Packers

3

Bed

2

Bath

12

Sleeps

$376.45

/ Nightly

Condo

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

Sheboygan, Wisconsin, United States

Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping boutiques. Unbeatable location in the heart of Sheboygan right on the riverfront boardwalk and easy walking distance to Lake Michigan's sandy beach. Fantastic amenities include world-class golf at Kohler and charter fishing expeditions available right out the back door.brbrSpread out in this large open-concept home with vaulted ceilings and 3 bedrooms, 2.5 bathrooms, and a loft space spread across two floors. Enjoy spectacular views from balconies on each floor.brbrOn either side of the building are several restaurants, and it's just a short walk to the sandy beach at Lake Michigan. Home is stocked with beach towels and folding chairs to enjoy at the beach. When you're ready for a break from sand and sun, there are games, puzzles, children's books, and toys available for your enjoyment. There are TV's with Roku to support your streaming services in each bedroom as well as the living room and loft areas.brbrSleep comfortably in bedrooms with great mattresses and quality bedding. Bedrooms are functional with dressers and closets with hangers and hampers. Upstairs there is a washer and dryer with laundry detergent and dryer sheets. Bathrooms are stocked with comfortable towels and hand soap, and shower gel and shampoo are also available for your use.brbrKitchen has everything you'll need to cook and dine at home or just heat up leftovers from Sheboygan's amazing restaurants. Kitchen appliances include dishwasher, oven, fridge, Keurig and drip coffee makers, and toaster. Dish soap, dishwasher detergent, garbage bags, and paper towels are all provided for your convenience. brbrBoat slips along the river in the Harbor Centre Marina are available for rent and managed by the City of Sheboygan Public Works. Please see their website for additional information.

Bed

Bath

Sleeps

$360.5

/ Nightly

Apartment

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan, Wisconsin, United States

Whether you're here to visit friends or family, this lower-level 2-bed, 1-bath Sheboygan vacation rental apartment has all the amenities needed to enjoy a relaxing trip. Prepare home-cooked meals in your fully equipped kitchen, unwind in your living room, or even enjoy some sunshine in the backyard. Enjoy a visit to John Michael Kohler Arts Center or fuel your wild side at Quarry Beach Adventure Park before enjoying a relaxing dinner and movie night at your home-away-from-home!

2

Bed

1

Bath

6

Sleeps

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