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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Guest favourite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

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. Unit NOT set up for babies or toddlers.

Oct. 19 – 26

$156 CAD per night

Guest favourite

Cottage in Oostburg

4.97 out of 5 average rating, 233 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Oct. 20 – 27

$251 CAD per night

Guest favourite

Townhouse in Sheboygan

4.97 out of 5 average rating, 117 reviews

Family Friendly Riverfront Escape|HUGE Game Room

Welcome to The WAVE – your ideal family friendly retreat nestled along the scenic Sheboygan River, just minutes from the beaches of Lake Michigan. As you step into The WAVE, you'll be greeted by a tastefully designed interior featuring LUX furnishings that exude both style and coziness. The accommodations include a King Suite with a riverfront balcony and a Guest Room with 2 queen beds. Entertainment is taken to a whole new level with our 500 sq ft game room with a 130-inch projection screen.

Nov. 6 – 13

$203 CAD per night

Guest favourite

Home in Waldo

4.97 out of 5 average rating, 62 reviews

Enjoy Spring & Relaxing in Waldo

Fully remodeled ranch house, that is nestled in the country, with over 2 plus acres of backyard with beautiful views of sunsets. Settled between Green Bay and Milwaukee, less than 20 miles to local attractions such as: Soul Winery, Parnell tower, Tiki Beach Resort, Road America, Kettle Moraine State Forest, Elkhart Lake, Harrington State Park, and Kohler Andrae State Park, and many local great supper clubs to get a bite to eat. Enjoy the country living vibe to reset from everyday life!

Feb. 21 – 28

$176 CAD per night

Guest favourite

Home in Sheboygan

4.97 out of 5 average rating, 151 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.

Jun. 20 – 27

$231 CAD per night

Guest favourite

Apartment in Sheboygan

4.92 out of 5 average rating, 398 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.

Nov. 1 – 8

$138 CAD per night

Guest favourite

Home in Sheboygan Falls

4.98 out of 5 average rating, 56 reviews

Adorable bungalow in historic Sheboygan Falls,WI

Cute bungalow located on a quiet cul-de-sac with a relaxing pond and a large fenced in yard. Centrally located within 20 minutes of Elkhart Lake, Whistling Straits and the shores of Lake Michigan. Also, it is a quick walk to quaint Downtown Sheboygan Falls where there is plenty of shopping, dining, parks, the Sheboygan River, and waterfalls. I also run a company called Rescue Dog Properties and will be donating 5% of all bookings to Paws Up Pet Rescue based in Sheboygan.

Aug. 31 – Sep. 7

$270 CAD per night

Guest favourite

Apartment in Kohler

5.0 out of 5 average rating, 158 reviews

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.

Feb. 13 – 20

$308 CAD per night

Guest favourite

Apartment in Sheboygan

4.84 out of 5 average rating, 184 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

Oct. 4 – 11

$98 CAD per night

Superhost

Guesthouse in Sheboygan

4.83 out of 5 average rating, 368 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!

Nov. 2 – 9

$172 CAD per night

Guest favourite

Apartment in Waldo

4.98 out of 5 average rating, 259 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Mar. 23 – 30

$154 CAD per night

Guest favourite

Apartment in Sheboygan

4.89 out of 5 average rating, 271 reviews

Spiritual Vibes Downtown Walk-up

New art and hand crafted decor. Some are even available for purchase, others are for guests to enjoy during their stay. Cozy, inviting, private apartment close to restaurants, shops and entertainment. Wonderful morning and evening light. Large deck for relaxing outdoors or enjoying the sun. We have a storage shed for bikes, strollers and the like if needed. Just give us the heads up and we'll give you the key.

Aug. 4 – 11

$144 CAD per night