Vacation rentals in Sheboygan Falls

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, 168 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

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, 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

A light blue front door is framed by neatly arranged red brick columns. Two lantern-style light fixtures are mounted on either side, providing a welcoming entrance. The door features a grid of glass panes, allowing natural light to illuminate the area.

4.94 out of 5 average rating, 234 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

4.95 out of 5 average rating, 176 reviews

An exterior view of the property features a wooden deck above with a railing, complemented by a staircase leading to the entrance. A paved area at the ground level includes plants and a grill, alongside a garage door and multiple windows of the main structure.

Home in Howards Grove

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

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.

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, 147 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.

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

The exterior of the Carriage House is shown, featuring a charming gray-brown facade with a garage door. A white entrance door is visible, framed by greenery and blooming white flowers in the foreground, enhancing the inviting atmosphere of the home.

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!

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Other great vacation rentals in Sheboygan Falls

5 out of 5 average rating, 70 reviews

Recombobulation Station-Locally Owned Surf Escape

LynseyRating, 5 stars4 days ago

Missy and Kyle's apartment in Sheboygan was truly a great recombobulation station! The location was spectacular with only two blocks to Lake Michigan in one direction and two blocks to great dining, farmers market, coffee shops, and local shopping in the other direction. The apartment was incredibly clean, cozy, and comfortable for some rest and relaxation in-between our local adventures. It was a lovely home away from home with everything you would need to prepare meals. And in the event you've forgotten something at home, there is a good chance Missy has thought about it for you.

4.93 out of 5 average rating, 27 reviews

A functional kitchenette features wooden cabinets and a granite countertop. A black refrigerator and coffee maker are visible. The open layout includes a dining table and seating. In the background, a bathroom entrance and additional countertop space can be seen, enhancing the convenience of the space.

Guesthouse in Sheboygan

Unique Guest House close to everything

ZachRating, 5 stars1 week 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.

The kitchen features modern cabinetry and a central island with two wooden bar stools. Stainless steel appliances, including a refrigerator and oven, are visible. Natural light enters through a window, illuminating the spacious countertops and kitchenware arranged neatly.

5 out of 5 average rating, 30 reviews

The Riverbed

CindaRating, 5 stars1 month ago

Janet's place was spotless, and everything seemed relatively new. Big kitchen that was well stocked, and comfortable seating in living area. Quiet neighborhood, plenty of parking space. The queen bed in the master was a bit firmer than I prefer, but not really a problem. We had a great stay!

Apartment in Sheboygan Falls

A bright corner features a comfortable chair next to a small table, set in front of large windows with blinds. A full-length mirror reflects the room, which showcases a stylish rug on the wood-like flooring and a glimpse of the bed in the background.

4.86 out of 5 average rating, 7 reviews

Elegant Condo in Sheb Falls

AlbertoRating, 5 stars9 months ago

Great place to stay for Road America.... will definitely stay here again!

A well-appointed bathroom features a marble countertop with a modern sink and a stylish mirror. A glass-enclosed shower with textured panels is present beside a clean toilet. Neutral tones in the walls create a calming environment.

Apartment in Sheboygan Falls

4.92 out of 5 average rating, 12 reviews

Country Apartment

StaceyRating, 5 stars22 months ago

Great place! Peaceful, country setting with places to eat within a short drive! It was super quiet! Would stay again!

A spacious outdoor deck features a modern fire table at its center, surrounded by comfortable seating. Lush trees and greenery line the riverbank, with a clear blue sky above. The tranquil river reflects the natural scenery, creating a serene setting for relaxation.

4.77 out of 5 average rating, 22 reviews

Sheboygan Riverside Condo

AngelaRating, 5 stars3 days 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!