Find Vacation Homes in Sheboygan County, WI from $153

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Top Cities in Sheboygan County

Vacation Homes in Sheboygan County

Vacation Home in Ellis Historical District

2.0 star property
9.6 out of 10, Exceptional, (12)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
$135 nightly
The price is $153
Nov 29 - Nov 30
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Vacation Home in Oostburg

9.6 out of 10, Exceptional, (216)
"Had a great family trip - backyard and beach are awesome. "
United States
Cheryl W.
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (120)
"Beautiful house, beautiful view, wonderful host"
United States
Cameron V.
Lake Michigan Home with gorgeous views, great spot for family or golf retreat

Vacation Home in Oostburg

10.0 out of 10, Exceptional, (116)
"We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process."
United States
Shelby L.
$150 nightly
The price is $158
Dec 1 - Dec 2
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (12)
"We enjoyed our stay. Jordan was great with communicating with us to see if we needed anything."
United States
Paul G.
LUXE Manor with Modern, Elegant Vibes

Vacation Home in Sheboygan

9.8 out of 10, Exceptional, (31)
"Wonderful accommodations. Great view and backyard on the River. Great place for our girls weekend in Sheboygan."
United States
Leslie M.
4 Bedroom Home on the River with Private River access

Vacation Home in Waldo

10.0 out of 10, Exceptional, (52)
"The theater room was amazing. "
United States
Daniel B.
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

Vacation Home in Elkhart Lake

10.0 out of 10, Exceptional, (35)
"Great time, spaciousness close to all activities "
United States
Gladys G.
Wander Back Inn to Elkhart Lake

Vacation Home in Plymouth

10.0 out of 10, Exceptional, (13)
"We were in town for a race at Road America.The house was very close and everything was as described. Great location and easy check in. We would definitely stay here again!"
United States
Mario G.
House Neighboring Road America and the Mullet River

Vacation Home in Sheboygan

9.8 out of 10, Exceptional, (84)
"Great location"
United States
Jamie L.
Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (4)
"Awesome place, we loved it!"
United States
Richard S.
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

Vacation Home in Oostburg

10.0 out of 10, Exceptional, (79)
"Convenient to Road America, great place for the kids, very quiet and secluded. "
United States
JD
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 10 beds!

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (21)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
$352 nightly
The price is $399
Nov 29 - Nov 30
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Vacation Home in Sheboygan

2.0 star property
10.0 out of 10, Exceptional, (13)
"Fabulous place to stay"
United States
Richard T.
New King Park Beach Lookout Deluxe! 3BR Right at Lake!

Vacation Home in Sheboygan

"Great house with adequate room for all 11 of us. Kitchen with new appliances, roomy and well supplied with dishes, glasses, pots, pans and cutlery. Beds were very comfortable. Backyard patio was wonderful. A great stay and would rent again. Only one problem, the dressers need to be secured to the wall to prevent any accident with younger guests."
United States
Terri M.
4- Bedroom Retreat w/ Sauna, Game Room, Patio & Walk to Golf, Bars & Restaurants

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (38)
"Very clean, cute, great communication, location & walkability! "
United States
Sandee M.
$355 nightly
The price is $403
Dec 3 - Dec 4
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Vacation Home in Ellis Historical District

10.0 out of 10, Exceptional, (1)
"Very clean, great communication, nice amenities! "
United States
Kelsey K.
Fully renovated, updated, and high-end finished 5 bedroom facing the marina!

Vacation Home in Plymouth

10.0 out of 10, Exceptional, (1)
"Nice home. Quiet area. Close to Road America "
United States
Roger M.
>>The Daydream Lodge<< @Racers Ridge

Vacation Home in Elkhart Lake

10.0 out of 10, Exceptional, (80)
"Such a wonderful place to stay!! There were plenty of games for our kids (age 2-7) and we enjoyed walking to dinner at night. The place is very clean and kitchen is well stocked to make cooking for the family easy. Highly recommend!"
United States
Lesli K.
Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!

Vacation Home in Sheboygan Falls

9.6 out of 10, Exceptional, (5)
"This place was perfect for a large group of us. Couldn’t ask for better and super convenient to Road America"
United States
david d.
Elm Park Farmhouse 4 Miles from Road America and 45 Minutes from Green Bay
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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Top Sheboygan County Hotel Reviews

Find out more about Sheboygan County

Booking Tips to Find the Best Sheboygan County Vacation Homes


How much does it cost to rent a vacation home in Sheboygan County?

You can find incredible Sheboygan County vacation homes for all types of budgets: between $153 and $403 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Sheboygan County?

If you are looking for a great deal on your vacation home in Sheboygan County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Sheboygan County?

There are 167 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Sheboygan County?

Begin by entering your trip dates to see what type of Sheboygan County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Sheboygan County?

Booking Sheboygan County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Sheboygan County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Sheboygan County along with your vacation property, into a Sheboygan County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Sheboygan County Vacation Homes information

Number of reviews
842
Accommodation
167 Vacation Homes
Lowest Price
$153
Highest Price
$403

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