Vacation rentals in Sheboygan County

The exterior of a two-story brick duplex is displayed, featuring symmetrical windows and a welcoming front porch adorned with an American flag. A well-kept lawn surrounds the house, with blooming flowers and neat landscaping. Soft evening light enhances the home’s inviting presence.

4.98 out of 5 average rating, 166 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!

4.99 out of 5 average rating, 269 reviews

Cabin in Elkhart Lake

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

4.64 out of 5 average rating, 310 reviews

A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

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.

The two-story home features a charming yellow exterior with white trim and a red metal roof. Flower baskets hang from the porch, which is framed by neatly manicured bushes and vibrant landscaping. A sidewalk leads to the entrance, enhancing accessibility.

4.83 out of 5 average rating, 260 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, 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!

4.71 out of 5 average rating, 105 reviews

An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.

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.

A stylish powder room features dark walls illuminated by modern wall sconces. A round mirror is placed above a sleek marble sink with brass fixtures. A towel hangs from a stylish ring, and a small plant adds a touch of greenery to the elegant space.

4.95 out of 5 average rating, 119 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, 140 reviews

An aerial view of a modern cabin showcases a spacious patio area with outdoor seating and a hot tub. Lush greenery surrounds the property, with a gravel driveway leading to the entrance. The cabin features large windows that allow for ample natural light.

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!

Gentle sand dunes are seen, adorned with tufts of green grass against a clear blue sky. The expansive view of Lake Michigan stretches into the horizon, with calm waters reflecting the sunlight.

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!

A round wooden dining table is surrounded by four white chairs, set against a light grey carpet featuring a geometric pattern. A bowl of yellow fruit sits in the center of the table. Natural light streams in from the adjoining area, enhancing the neutral tones of the space.

4.98 out of 5 average rating, 144 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.

A sandy beach is set against a clear blue sky, with gentle waves lapping at the shore. Lush green grass borders the beach area, while several volleyball nets are positioned on the sand, indicating recreational opportunities nearby.

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.

Vacation rentals for every style

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Popular amenities for Sheboygan County vacation rentals

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Other great vacation rentals in Sheboygan County

A sleek entertainment area features a large flat-screen television mounted on the wall. Below, a modern black console showcases an electric fireplace with glowing embers. A potted plant adds a touch of greenery beside the staircase, enhancing the room's contemporary design.

4.71 out of 5 average rating, 24 reviews

6+ Guest Home

TylerRating, 5 stars1 month ago

Great stay. Great location. Stephanie was responsive. Place was clean. Corner bar was amazing - sandwiches the size of your head for a good price. Would stay again

An outdoor fire pit area is surrounded by vibrant red chairs arranged in a circle. The sun sets over Lake Michigan, casting a warm glow on the grassy landscape, which gently slopes towards the beach. Additional seating is visible nearby.

4.94 out of 5 average rating, 51 reviews

3-bdrm beachfront home on Lake Mich, Sheboygan WI

JohnRating, 5 stars7 months ago

Now that I have stayed at Jack's home @ 5 times, I can easily verify that every moment spent in that home is magical - steps away from a walk on the beach, the methodical waves lapping on the shoreline, and the majestic sunrises reflecting on the water combine to provide a therapeutic sensory experience that delivers 24 hours each day. If that isn't enough, there are fabulous coffee shops, restaurants, and bars that you can walk to as well as many others a short drive away. No - Jack does not pay me to write these reviews ... the reviews write themselves. Enjoy!

4.96 out of 5 average rating, 23 reviews

A sunroom is highlighted by large windows that provide views of the surrounding nature and river. A stone fireplace adds warmth to the space, complemented by a beige area rug on the wooden floor. Potted plants decorate the windowsills, enhancing the inviting atmosphere.

Home in Sheboygan Falls

“On The Water” the Sheboygan River Overlook

JessieRating, 5 stars3 days ago

We were in town for a wedding and needed a place to stay close to the Kohler property. Dan's place is a true hidden gem. The views from the backroom and backyard are beautiful. We had an amazing time kayaking and just spending time outside. The town is a short walk from the Airbnb and has tons of cute places to grab a drink or food. We also had no problem getting Ubers to the wedding events. Dan is so attentive and responsive! I hope we find our way back to this Airbnb again!

The image captures a scenic view from the deck, showcasing a lush green backyard leading to the shoreline of Lake Michigan. A fire pit is visible on the grass, and white planters frame the deck, while the sky displays a soft gray hue.

4.94 out of 5 average rating, 199 reviews

Beachfront getaway in Sheboygan

DanRating, 5 stars3 weeks ago

To find a place in the middle of Sheboygan and right on the beach was fantastic. We loved the location but everything about the house was really perfect. Easy, super clean, and comfortable in every way.

A fully equipped kitchen features white cabinetry and a marble countertop. Natural light illuminates the space through multiple windows, enhancing the modern appliances, including a stainless steel dishwasher and stove. A coffee maker is positioned near the sink, with kitchen essentials neatly arranged.

4.57 out of 5 average rating, 14 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

ClaudiaRating, 5 starstoday

Chris was a great host! Our other Airbnb didn’t respond to us and he was able to get us in with a same day reservation! He was very friendly, brought us a high chair and provided some local snacks for our stay! The house was spotless and the backyard and neighborhood were so cute! We will be staying with you again next time we’re in Sheboygan!

A well-lit kitchen is presented, featuring white cabinetry and a granite countertop. Kitchen appliances and supplies are organized neatly, with a wooden stool positioned near the counter. Natural light enters through the window, highlighting the open layout and warm wooden flooring.

4.96 out of 5 average rating, 25 reviews

State Park w/ Orchard Style Yard & Pavilion

AnnaRating, 5 stars8 months ago

We had a great stay at The Orchard House Retreat. The property is as described, looks like the pictures and had everything we needed. The kids especially loved all the toys and books! The house is 5 min to the State Park beach and 10 min from downtown. We loved having the backyard, the furniture was well taken care of and the fire pit was perfect for s’mores. The hosts were very responsive and accommodating— with everything labeled around the home. It’s also a great layout for bigger families /groups with 2 bedrooms upstairs, 1 on the main floor and 1 in the basement.

4.96 out of 5 average rating, 23 reviews

An aerial view captures the beachfront condo complex and its surroundings, showcasing well-maintained buildings with red roofs. The sandy beach and Lake Michigan are visible in the background, alongside a pier, offering a glimpse of the tranquil coastal environment.

Villa in Sheboygan

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

MikeRating, 5 stars7 months ago

Great host!! Great location!! Great property!! We came in town for a golf trip and this property was a perfect location and comfortable. Nice to start each morning with a quick walk to the beach and watch the sun rise over the lake. Would definitely stay here again and would recommend it to anyone looking to stay in the area.