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Compare 295 Vacation Homes in Sheboygan with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (33)
"Great place and so quiet!!"
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

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

10.0 out of 10, Exceptional, (17)
"Very comfortable space. "
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Elkhart Lake, WI home close to lake, downtown, and Road America racetrack

10.0 out of 10, Exceptional, (2)
"House was nice and clean. Good location."
Elkhart Lake, WI home close to lake, downtown, and Road America racetrack

Welcome to the "Lake Cottage" where lake Michigan waves are calling

10.0 out of 10, Exceptional, (124)
"This is our second time staying at The Cottage and it was just the relaxing weekend away that we needed! The hosts were super...they thought of everything and had gone above and beyond to make sure we had everything we needed. "
Welcome to the "Lake Cottage" where lake Michigan waves are calling

Spacious 5-Bedroom Retreat House In Chilton, WI!

10.0 out of 10, Exceptional, (3)
"The pictures don’t do justice to how nice this place was. Highly recommend for a large group. "
Spacious 5-Bedroom Retreat House In Chilton, WI!

Riverfront Sheboygan Townhome w/ Grill!

10.0 out of 10, Exceptional, (14)
"Beautiful, clean accommodations right along the river!"
Riverfront Sheboygan Townhome w/ Grill!

4 Bedroom Home on the River with Private River access

9.8 out of 10, Exceptional, (26)
"This charming house has plenty of space for families or friend groups and is just a short drive to all of the local attractions. We had a wonderful stay and look forward to coming back again!"
The price is AED 984
AED 1,563 total
includes taxes & fees
12 Jun - 13 Jun
4 Bedroom Home on the River with Private River access

Lake Breeze on 11th

10.0 out of 10, Exceptional, (1)
"Enjoyed staying at the property, we brought our two dogs just a heads up for dog owners. The backyard is not fenced so if you have a runner, it might be hard. Other than that, the house is comfortable, the beds were comfortable, the bathroom was clean, and the kitchen was stocked. Parking was easy and the neighborhood is quiet. Easy location to get to everything in Sheboygan. Dan was easy to get a hold of and the process went very smooth. Just a note, both bedrooms are upstairs and the bathroom...
Lake Breeze on 11th

Cozy Cape Cod Home

10.0 out of 10, Exceptional, (26)
"Easy access, quiet neighborhood, comfortable accommodations"
Cozy Cape Cod Home

The Esker Ridge Chalet, Pristine Elkhart Solitude

10.0 out of 10, Exceptional, (52)
"We loved our short stay at the Chalet--the hosts are friendly and polite, the space is well-equipped, and the beautiful Wisconsin woods surrounding us made for a tranquil winter holiday. We would highly recommend a visit!"
The Esker Ridge Chalet, Pristine Elkhart Solitude

Grand Rural Wisconsin Retreat: Full Indoor Gym

10.0 out of 10, Exceptional, (5)
"This place is amazing! Perfect and accommodating for large groups! It was a great experience and fit our needs well! The kids really enjoyed the on-site basketball gym and game room!"
Grand Rural Wisconsin Retreat: Full Indoor Gym

Beach House- 3 blocks to beach, Huge patio, Sauna, Fire Pit and 2 bikes! 🚲🔥🌊

9.8 out of 10, Exceptional, (36)
"Great stay. Location is awesome. Price is just right."
Beach House- 3 blocks to beach, Huge patio, Sauna, Fire Pit and 2 bikes! 🚲🔥🌊

Road America Adjacent Lake House with indoor pool

9.8 out of 10, Exceptional, (28)
"Amazing place really clean the host was amazing"
Road America Adjacent Lake House with indoor pool

'Twilight' - Just a few steps down to Lake Winnebago!

9.8 out of 10, Exceptional, (10)
"A comfortable, relaxing home along the lake, with nice sounds of the waves crashing on the shore."
'Twilight' - Just a few steps down to Lake Winnebago!

Beautiful Lake House on the Shores of Erler Lake.

9.6 out of 10, Exceptional, (206)
"My husband and I decided to get away after Christmas for some down time. We didn’t want to drive too far, but wanted somewhere secluded. This place was ideal. The trails are really nice, it’s very quiet and just what we needed. I rated it a 4 out of 5 only because there was no light in back so we always needed a high powered flashlight if we needed to take our dogs out and there are no window coverings over the front door, so when sitting in the front room watching TV anyone could look in since...
Beautiful Lake House on the Shores of Erler Lake.

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

10.0 out of 10, Exceptional, (105)
"This place is very clean and comfortable.The staff is very kindness. "
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

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

9.6 out of 10, Exceptional, (131)
"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

East River Retreat, WATERFRONT🛶+ Fire Pit🔥Pet friendly 🐾

9.4 out of 10, Exceptional, (49)
"Love this place! Have stayed multiple times. Always very relaxing to come back and relax after a long day of work."
East River Retreat, WATERFRONT🛶+ Fire Pit🔥Pet friendly 🐾

Beach and Golf House

10.0 out of 10, Exceptional, (60)
"We truly enjoyed our stay. The owner takes great care of the home and it was incredibly clean. It's in walking distance to the lake and in a lovely neighborhood. Great for families or a group. Highly recommend "
Beach and Golf House

Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views

10.0 out of 10, Exceptional, (36)
"Very beautiful property. Sooooo many great amenities that many other property rentals do not offer. Beautiful view, very clean, easy check in and check out process. We would definitely return. Thank you for hosting us!"
Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views
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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