Photo by Stephanie Kay

Holiday Homes in Sheboygan Falls

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Featured Holiday Homes in Sheboygan Falls

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

10.0 out of 10, Exceptional, (13)
"We stayed for Thanksgiving week. It met my expectations completely! "
The price is AU$582
includes taxes & fees
21 Jan - 22 Jan
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Charming 2-bedroom Lake House in West Bend

10.0 out of 10, Exceptional, (2)
"I rented this for my parents Christmas week. They said everything was clean decorated beautiful. We will probably rent again in 2025!"
Charming 2-bedroom Lake House in West Bend

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (234)
"Such a cozy spot to spend a special weekend getaway! Mark allowed our 2 pups to join and did everything to make sure we had a comfortable stay. The view was outstanding, the home was spotless and the art gallery was so cool. We felt comfortable from the moment we walked in. Highly recommend!"
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck

9.8 out of 10, Exceptional, (19)
"Very nice townhome with lots of toys (games) for those who want to hang out. Tried to use the gas heater on deck overlooking the River but, it wouldn’t light."
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

10.0 out of 10, Exceptional, (97)
"We just love everything about this place! It's super clean, beautifully decorated (and so festive around the holidays!), cozy, comfortable and in such a peaceful location. The hosts are always great too. This is our third time coming around the holidays and we always look forward to it. Maybe this year we'll try to go in the summer too :) "
The price is AU$241
includes taxes & fees
21 Jan - 22 Jan
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!

10.0 out of 10, Exceptional, (71)
"We love staying here and will be back next year!"
Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

9.4 out of 10, Exceptional, (184)
"We stayed in the fall with family ranging from 7-65. The beach and view was so beautiful and relaxing. There was plenty of room to spread out or all be together. The games in the basement were the highlight for all ages. "
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

9.6 out of 10, Exceptional, (130)
"This home had everything we needed for a relaxing family stay. We played games in front of the fire and exercised our dog in the (surprise!) fenced-in backyard. "
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

4 Bedroom Beachfront Condo - Fantastic Lake View

10.0 out of 10, Exceptional, (62)
"Great location and very welcoming"
4 Bedroom Beachfront Condo - Fantastic Lake View

NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

10.0 out of 10, Exceptional, (27)
"Great house. Super clean ans spacious. We hosted family Christmas. Everything was perfect. Hope to stay again next year."
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

Dog-Friendly Sheboygan Home - 1 Mi to Town!

9.8 out of 10, Exceptional, (7)
"We just stayed there a few weeks ago and when we left we said we would definitely stay here again! Well equipped, exceptionally clean, and well located. Nice yard in the back for doggies, and the treats were nice! Management was very accommodating and easy to communicate with. Rick Doerr "
Dog-Friendly Sheboygan Home - 1 Mi to Town!

Riverfront Sheboygan Townhome w/ Grill!

10.0 out of 10, Exceptional, (13)
"My family and I were visiting family in Sheboygan over Christmas. The owner decorated the condo with a Christmas tree and other holiday decor. This condo was by far one of the most well put together condos we have stayed in. The toiletries in the condo were all high-end products. The condo was in a great location, property manager was responsive, and very clean. My family and I would definitely stay at the condo again. This condo is definitely a 5-star property. "
Riverfront Sheboygan Townhome w/ Grill!

Modern Townhome w/ Deck - 1/2 Mi to Elkhart Lake!

10.0 out of 10, Exceptional, (34)
"Great stay, great location!"
Modern Townhome w/ Deck - 1/2 Mi to Elkhart Lake!

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

10.0 out of 10, Exceptional, (173)
"Amazing host, house and location! The house was spotless and the hot tub was a hit! Very easy to follow instructions were provided. The host was very responsive, no issues and would recommend to anyone!"
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Lake House w/ 6-BR's near Kohler-Andrae/Sheboygan

10.0 out of 10, Exceptional, (15)
"This house was perfect for our group of 10 lifelong friends. The location is beautiful. The house was so well laid out for a group. And the amenities were wonderful. Thanks Jeremy and crew for enabling us to have a fantastic weekend! "
Lake House w/ 6-BR's near Kohler-Andrae/Sheboygan

Oostburg,WI Beach front, Lake Michigan

9.8 out of 10, Exceptional, (61)
"I didn’t leave for 4 days except to take long walks with my dog. It was very relaxing and so quiet. This is the fourth year that my dog and I have been here and we will be back again next year! So nice to have a lot of beach to walk on."
Oostburg,WI Beach front, Lake Michigan

5 Bedroom Modern House

9.6 out of 10, Exceptional, (9)
"Great location and rooms were very spacious. Plenty of room for our group of 9 and close to blue harbor and DT area. Very cute back patio. Property manager was very responsive. Would stay here again!"
5 Bedroom Modern House

Historical Lodge in Elkhart Lake with Hot Tub

9.8 out of 10, Exceptional, (6)
"This location was awesome. it exceeded our expectations. had well working games in the basement including pinball machines. The bathroom very clean. hot tub very clean and worked like brand new. I couldn't recommend this place enough! thank you for sharing your home with us!!"
Historical Lodge in Elkhart Lake with Hot Tub

Near Milwaukee - Sleeps 12 - Add The Pontoon

8.6 out of 10, Excellent, (10)
"With a beautiful southern exposure and sunny views of a gem of a lake, this place is very relaxing and welcoming as a rental home. The views from the porches are equally as inviting with plenty of spaces to enjoy inside and out. A well appointed kitchen, comfortable beds and bedding and the price put this lake house on the top of our return list!"
Near Milwaukee - Sleeps 12 - Add The Pontoon

4 Bedroom Home on the River with Private River access

9.8 out of 10, Exceptional, (24)
"Great house right on the river. Plenty of bedrooms to spread out. Nice, eclectic decor. Easy peasy check-in/out. Would like to come back in the summer sometime to take advantage of the fire-pit and the kayaks. Made visiting our family a breeze. "
4 Bedroom Home on the River with Private River access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Sheboygan Falls

6 Bedroom house on 7 acres

9.6 out of 10, Exceptional, (25)
"House was perfect for our large group. Lots of space to hang out together, but then plenty of private bedrooms. Especially enjoyed the large firepit and open kitchen."
6 Bedroom house on 7 acres

Country beauty on 5 acres

10.0 out of 10, Exceptional, (84)
"Our stay was very lovely and convenient. Located less than 20 mins from Road America and plenty of private rooms for the family to spread out at night to sleep. "
Country beauty on 5 acres

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (878)
"The 2 separate, private bedrooms with the living room and kitchen worked very well for my family. "
The price is AU$171
includes taxes & fees
17 Feb - 18 Feb
Grandstay Residential Suites Hotel - Sheboygan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.