Holiday houses in Sheboygan

4.98 out of 5 average rating, 169 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

4.83 out of 5 average rating, 263 reviews

Home Away From Home-One Block From Lake Michigan!

Centrally located and pet-friendly! Walk to the beach, parks, and downtown Sheboygan. This spacious two-story home perfect for groups features flexible bedroom setups, a fully equipped kitchen, dining room, fenced backyard, and parking for up to 4 vehicles. Base pricing is competitive for small groups $15/guest per night for more than 2 guests. Close to golf courses, many family spots, restaurants, and 16 miles from Road America. Watch “Sheboygan Airbnb” on YouTube for a full walkthrough!

5 out of 5 average rating, 123 reviews

Apartment in Kohler

The Hemingway on Church - It Tolls For Thee

"Kristine's property has all the charm of a modern day Mayberry" -Michael This 1906 historic home is nestled in the heart of the equally historic "Village of Kohler." Completely remodeled in 2019 adding Kohler spa amenities and modern touches to its original charm. Mixing modern & antique furniture finds like the Hemingway Sideboard (which inspired the literary theme) make this historic hideaway a true Kohler destination. "You cannot get a better location in Kohler than this house!" -Dennis

4.98 out of 5 average rating, 201 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully landscaped and decorated boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with Stearns and Foster King size bed. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

4.95 out of 5 average rating, 121 reviews

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

5 out of 5 average rating, 214 reviews

Woodland Creek Retreat: explore & relax!

Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

4.98 out of 5 average rating, 148 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

4.96 out of 5 average rating, 188 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

4.93 out of 5 average rating, 499 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

4.84 out of 5 average rating, 223 reviews

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

4.82 out of 5 average rating, 460 reviews

Guesthouse in Sheboygan

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

4.9 out of 5 average rating, 134 reviews

Spacious Home Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our 3 bedroom home near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. Send me a message to find out about our other available listings.

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Other great holiday rentals in Sheboygan

4.86 out of 5 average rating, 63 reviews

Lovely 1 Bedroom Serviced apartment in Sheboygan

ShonRating, 5 stars5 months ago

Think of the town in Hallmark winter movie setting. that's exactly where this place is located. super quaint and cute. Big Window to look out at the town. very cozy and perfect for 2. the bed was really comfy. my only draw back is I wish the living room Tv was bigger. but they may ju be me, I can barely see lol. Other than that I loved it! Would absolutely come back.

5 out of 5 average rating, 37 reviews

Unmatched Location, Views, & Style. Welcome Home!

CarlyRating, 5 stars5 days ago

This house is amazing!! Sparkly clean. It has beautiful natural daylight, and you can open all the windows to feel a nice breeze during the day. It’s well-stocked and has supplies for the beach, which was a major plus! Jill is very nice and was easy to get ahold of!

5 out of 5 average rating, 16 reviews

Beachside Beautifully Renovated Historic Home

AmyRating, 5 stars19 months ago

Beautiful, well-appointed home with a heck of a view AND walking distance to downtown. Tricia was communicative and kind. Great experience!

4.93 out of 5 average rating, 90 reviews

Condo in Sheboygan

Janelle's Dockside Condo

KathleenRating, 5 stars2 weeks ago

Janelle’s place was spacious and sparkling clean. The location is great, right on the river and an easy walk to the lake. We would definitely stay again if we come back to Sheboygan.

4.98 out of 5 average rating, 98 reviews

Loft in Sheboygan

Spacious/stylish, 2br loft

AmyRating, 5 stars1 month ago

Great place in a convenient Sheboygan location. Excellent communication from host. Lots of stairs to get to the apt, so made hauling up our stuff a bit of an endeavor. Would be hard for folks w physical limitations. Very spacious place was great for entertaining our group. Bathrooms are strangely situated (because this used to be an office, I think), and the farthest bedroom is quite a haul from the closest bathroom. Not a problem but may be helpful to know. Spotless, sunny and well equipped. Thank you!

4.95 out of 5 average rating, 58 reviews

Guest suite in Waldo

Above Garage Apartment w/ Private Beach

AlexRating, 5 stars2 weeks ago

I don’t think we could have found a better place to stay. Dustin and his family were incredible hosts. Very clean and cozy. The swimming hole is PERFECT! Beautiful home and views. This will definitely be somewhere we return to regularly as long as they’ll have us! Cannot recommend it enough.

5 out of 5 average rating, 36 reviews

Villa in Sheboygan

Lovely Lake Lookout - Cozy Condo Steps from Lake

StewardRating, 5 stars1 month ago

Danielle had a perfect place for us to stay long-term. The location is great: there are a variety of restaurants nearby, a wonderful coffee shop, the ice cream parlor opened for the season, Blue Harbour is right next door, and of course Lake Michigan. There is easy access to the beach area, including enough beach to enjoy. Our hosts were very friendly and responsive. If we had any questions or concerns, they responded immediately. When we needed to extend our stay, they worked with us to be able to do that. Fantastic hosts! The decor is warm and friendly. It definitely felt welcoming and comfortable. The only issue was with the drainage in the tubs (a bit slow), but they were addressing that, and hopefully it will be resolved. We would definitely recommend staying with Danielle!