Vacation rentals in Sheboygan Falls

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Top-rated vacation rentals in Sheboygan Falls

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

Apartment in Sheboygan

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, 275 reviews

Top guest favorite

The kitchen features dark cabinetry with artistic landscape designs and a large white countertop island. Stainless steel appliances include a stove and dishwasher, while a coffee maker is positioned on the counter. Natural light enters through a nearby doorway, illuminating the warm wood tones of the floor.

Home in Plymouth

The 2400 sq ft Plymouth Paddock near Road America!

This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race fans looking for a home during race weekend. Only 4 miles from Road America the location is close to all of Sheboygan County's finest attractions. Located two blocks from downtown on a quiet street, its up to you how you want to spend your evening. You could walk downtown for a bite, have a campfire, make a meal, or just spend time together. Welcome to your home away from home!

4.97 out of 5 average rating, 207 reviews

Guest favorite

The kitchen features a spacious granite countertop and a black sink, highlighted by wooden cabinetry. A large window allows natural light to fill the room, showcasing scenic outdoor views. Colorful yellow chairs and a small table create a cozy seating area nearby.

Home in Sheboygan

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

4.96 out of 5 average rating, 145 reviews

Top guest favorite

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

Home in Sheboygan

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

4.98 out of 5 average rating, 165 reviews

Top guest favorite

A bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.

Home in Sheboygan

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

4.96 out of 5 average rating, 125 reviews

Top guest favorite

A serene riverside view is framed by tall trees, showcasing a natural pathway leading to the water. A circular stone firepit is visible, complemented by two small white chairs, providing an inviting outdoor seating area.

Home in Sheboygan Falls

“On The Water” the Sheboygan River Overlook

The views from inside make it feel as if the home is overhanging the beautiful Sheboygan River. Go kayaking, enjoy the historic downtown, relax in the sunroom warmed by a fireplace, or sit out back on the deck. These are just some of the things this space has to offer. You are between several great golf courses including Whistling Straights & The Bull, & just 15 minutes from Road America. You will love the eclectic comfort & atmosphere of this spacious 2 bedroom 1 1/2 bath home! Memories await!

4.95 out of 5 average rating, 85 reviews

Top guest favorite

A cozy two-story home nestled among tall trees, featuring a spacious front porch and a gravel driveway leading to a two-car garage. Lush greenery surrounds the property, providing a serene and inviting woodland atmosphere.

Home in Sheboygan

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,deer and giant woodpeckers. Great wood burning fireplace and epic game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

5.0 out of 5 average rating, 250 reviews

Top guest favorite

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

4.96 out of 5 average rating, 183 reviews

Guest favorite

A kitchen features light green walls and wooden ceiling beams, enhancing a spacious layout. Modern appliances are complemented by white cabinetry and a large island with bar seating. Natural light fills the room through multiple windows, providing an inviting space for meal preparation.

Apartment in Sheboygan Falls

The Historic Downtown Suite

Located in the historic downtown district of Sheboygan Falls, the Historic Downtown Suite seamlessly blends classic charm with modern luxury. Guests can enjoy convenient access to world-renowned golf courses, including Blackwolf Run, The Bull at Pinehurst Farms, and Whistling Straits, as well as the exhilaration of Road America, just a 15-minute drive away. Immerse yourself in the suite’s luxurious accommodations while discovering the many attractions this vibrant area has to offer.

4.96 out of 5 average rating, 25 reviews

Top guest favorite

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

Apartment in Sheboygan

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.

4.98 out of 5 average rating, 218 reviews

Guest favorite

A comfortable living area features a sectional sofa in a soft grey hue, a rustic wooden coffee table, and natural light streaming through large windows. Unique décor includes a vintage style chair and a wall-mounted shelf with plants and books.

Apartment in Sheboygan

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.

4.93 out of 5 average rating, 594 reviews

Top guest favorite

A neatly arranged countertop displays a candle labeled 'Blush Floral' alongside a clear vase filled with fresh red roses. A sleek soap dispenser, marked 'Church Street Hand Soap,' sits prominently, enhancing the serene ambiance of the space.

Apartment in Kohler

Church Street Romance & Retreats-Village of Kohler

“A well-appointed, cozy and stylish retreat close to everything in Kohler.” -Kim Take the stairs to my secluded 2nd floor tree view retreat! A private side entrance and open floor plan flanked by two bedrooms makes this unit perfect for couples or a girl's getaway spa weekend. Romantic turn-of-the-century touches meet modern convenience & comfort. Baker furniture, previously a Kohler Company, can be found throughout the apartment enhancing your Village of Kohler stay.

5.0 out of 5 average rating, 227 reviews