Holiday rentals in Kohler

4.98 out of 5 average rating, 170 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, 272 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.

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

4.89 out of 5 average rating, 97 reviews

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

4.97 out of 5 average rating, 211 reviews

Home in Sheboygan

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

Home in Sheboygan

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!

Superhost

Barn in Sheboygan Falls

4.71 out of 5 average rating, 105 reviews

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, 144 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, 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.

4.93 out of 5 average rating, 501 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.

Superhost

Guest house in Sheboygan

4.82 out of 5 average rating, 460 reviews

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!

Superhost

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.

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Other great holiday rentals in Kohler

Serviced apartment in Sheboygan

5 out of 5 average rating, 9 reviews

New Two Bedroom Stay.

MariaRating, 5 stars1 week ago

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.

4.93 out of 5 average rating, 27 reviews

Guest house in Sheboygan

Unique Guest House close to everything

ZachRating, 5 stars2 weeks ago

Our stay was perfect and had no hiccups. Easy to find and follow instructions. I look forward to booking again next year for our yearly trip.

Earthen home in Elkhart Lake

4.98 out of 5 average rating, 82 reviews

Camp Skywood - Elkhart Lake - Road America

AliciaRating, 5 stars3 days ago

We had a wonderful time! Beautiful, inspiring house and gorgeous nature and scenery!

5 out of 5 average rating, 38 reviews

Guest suite in Sheboygan

Unmatched Location, Views, & Style. Welcome Home!

AveleneRating, 5 stars2 days ago

This Airbnb was one of the best we’ve ever been to! The views alone are stunning! We loved seeing the water from the beautiful living area. This house is pristine, felt airy, and was very clean. We had all the amenities we needed. It’s in the heart of everything and is walkable too. Because of its prime location, there was activity on the street but we brought sound machines with us and it was just fine. We can’t wait to come back.

Home in Sheboygan

4.77 out of 5 average rating, 22 reviews

Sheboygan Riverside Condo

AngelaRating, 5 stars1 week ago

Loved the place. Right on the river. Balcony view is great along with the fireplace! Renter was responsive and allowed us to check in early. Can’t wait to go back!

4.98 out of 5 average rating, 41 reviews

Villa in Plymouth

Luxury Retreat near Road America

MelissaRating, 5 stars2 months ago

Amazing Stay – Impeccably Clean and Comfortable! I had an incredible stay at this home! From the moment I walked in, I was impressed by how spotless everything was. The space was not only beautiful but also meticulously cleaned, making it feel fresh and welcoming. The host clearly takes great care in maintaining the home, and it showed in every detail—from the crisp linens to the sparkling kitchen and bathroom. Beyond the cleanliness, the home was well-equipped with everything I needed for a comfortable stay. The bed was super cozy, and the atmosphere was peaceful, making it easy to relax. Communication with the host was seamless, and they were friendly and responsive. I highly recommend this place to anyone looking for a top-notch Airbnb experience. I would absolutely stay here again!