Holiday houses in Sheboygan County

4.98 out of 5 average rating, 171 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!

4.64 out of 5 average rating, 311 reviews

Apartment in Plymouth

Pineyard Plymouth Apartment

Enjoy this older upper floor apt. with two single bedrooms with a twin bed in one and a full bed in the other, full bath, kitchen, living room, and off street parking. VCR/DVD player and internet is available. Kitchen is equipped with dishes, pots, pans, stove, and refrigerator. We are five minutes from Road America, fifteen minutes from Sheboygan, and thirty minutes from Fond du Lac. Only three blocks from downtown Plymouth enjoy many shops and eating establishments. Pets are NOT allowed.

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

Guest favourite

4.97 out of 5 average rating, 211 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, 202 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!

4.71 out of 5 average rating, 106 reviews

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

5 out of 5 average rating, 145 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

4.98 out of 5 average rating, 150 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, 189 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, 502 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.

4.82 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!

4.83 out of 5 average rating, 304 reviews

Sheboygan Surf House - The Elbow

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our newly remodeled Urban living oasis is a studio and a half that is conveniently located in the heart of downtown, just steps from renown bars and restaurants and only blocks to Lake Michigan, The Sheboygan River, South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake or leisure time SSH is perfect for you.

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Sheboygan County holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sheboygan County

5 out of 5 average rating, 40 reviews

Guest suite in Sheboygan

Unmatched Location, Views, & Style. Welcome Home!

AbbyRating, 5 starstoday

This place is amazing! It is impeccably clean—not a speck of dust anywhere. It is a beautiful space with gorgeous views and yes, tons of natural light! It is close to lots of things to do and places to eat. We enjoyed our stay!

4.96 out of 5 average rating, 26 reviews

Home in Sheboygan Falls

“On The Water” the Sheboygan River Overlook

GraceRating, 5 stars1 week ago

The cottage is absolutely beautiful—quaint, peaceful, and right along the river which made it even prettier. Everything here was so thoughtfully prepared as it felt cozy and charming while also being fresh and comfortable. I couldn’t have asked for a better place to stay for a summer trip with my friends.

5 out of 5 average rating, 10 reviews

Terrace View a Charming 1 Bedroom Apt

DonteRating, 5 stars30 months ago

Doug was an excellent host making sure everything was perfect during my stay if im ever in Sheboygan again I’ll definitely be staying here again.

4.99 out of 5 average rating, 89 reviews

Home in Sheboygan Falls

Adorable bungalow in historic Sheboygan Falls,WI

MelissaRating, 5 stars4 days ago

We stayed for a week and felt right at home! It was spacious, well maintained and decorated, and had more than we needed. We especially loved the fenced in yard with decorative pond and the game room downstairs. We would definitely stay here again.

Guest favourite

Condo in Sheboygan

4.93 out of 5 average rating, 90 reviews

Janelle's Dockside Condo

KathleenRating, 5 stars3 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!

Guest favourite

Condo in Sheboygan

4.88 out of 5 average rating, 206 reviews

Beachside Lake View - 2br - First Floor - Garage

RobinRating, 5 stars7 months ago

Beautiful location. Everything was great from the beginning to the end of our stay. We can’t wait to go back for another stay.