Holiday rentals in Sheboygan

4.98 out of 5 average rating, 167 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, 262 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

Flat 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

4.97 out of 5 average rating, 209 reviews

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft 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 entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

4.98 out of 5 average rating, 200 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!

4.98 out of 5 average rating, 145 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, 186 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.

4.96 out of 5 average rating, 129 reviews

Good VIBES On the Third COAST- Pets Welcome

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

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

Guest house 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, 133 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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Popular amenities for Sheboygan holiday rentals

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Free parking on premises

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Other great holiday rentals in Sheboygan

5 out of 5 average rating, 69 reviews

Recombobulation Station-Locally Owned Surf Escape

MaraRating, 5 stars2 weeks ago

Absolutely beautiful place to stay. I had a wonderful time and would stay here again. Very walkable and Missy was a fantastic host. Very comfortable place. Huge bathroom! The kitchen was stocked and wonderful. I can’t say enough good things about this location and the hosts.

5 out of 5 average rating, 8 reviews

New Two Bedroom Stay.

MariaRating, 5 starstoday

Inside of place is great. Nice, clean, updated, and had what we needed. Tip - if 4 people staying for a few days bring your own toilet paper, paper towels, and maybe extra shower towels. 5 minute drive to Lake Michigan/beach and 5-10 minute drive to cute and fun bars, restaurants, etc.

4.89 out of 5 average rating, 62 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.

4.96 out of 5 average rating, 82 reviews

House Near the Lake

BrianRating, 5 stars5 days ago

Loved the place. Felt right at home. Made sure that we had everything we needed and to reach out if there was a problem! Nice and quiet neighborhood. Highly recommend and can't wait to be back!

4.97 out of 5 average rating, 31 reviews

Apartment in Sheboygan

Heavenly Condo in the Malibu of the Midwest

LisaRating, 5 stars3 months ago

Debbie was super responsive from day 1 onward. Really enjoyed working with her for our 6-day stay. The place was nice and warm despite the sub-zero temps we had when there. Bed was comfortable and lots of hot water for showers. New appliances so meals in were easy. All in all a great place to stay. Thank you Debbie.

5 out of 5 average rating, 89 reviews

Cottage in Sheboygan

Cozy one bedroom cottage near lake Michigan!

LeishaRating, 5 stars6 days ago

Very private and quiet! Clean, tidy, well-stocked kitchen and bathroom. 15 minute brisk walk to North Point Overlook. Easy drive to area restaurants and attractions. Kohler museums are a must!

4.9 out of 5 average rating, 86 reviews

One Bdrm Apt - The Erie House near lake & downtown

JanRating, 5 stars1 week ago

Sarah's place was comfortable and well-equipped. We were able to walk to the downtown event for which we made the trip. Our stay was short, but I am sure we'd have made better use of the facilities and surroundings in a longer stay.