Book Holiday Homes in Sheboygan

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Featured Holiday Homes in Sheboygan

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

Brillion
Book a stay at this family-friendly vacation home in Brillion. Enjoy free WiFi, laundry facilities, and patios. Our guests praise the helpful staff in our ...
Opens in a new windowLarge, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

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

Oostburg
Book a stay at this beach vacation home in Oostburg. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Oostburg Public Library and Veteran's ...
Opens in a new windowLarge Unique & Artistic Lake Michigan Beach House / Awesome Game Room
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

Two Rivers
Stay at this vacation home in Two Rivers. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Rogers Street Fishing Village and Historic Washington ...
Opens in a new windowNew! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
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The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude

Elkhart Lake
The price is NZ$453 per night from 23 Sept to 24 Sept
NZ$453
23 Sept - 24 Sept
includes taxes & fees
Stay at this vacation home in Elkhart Lake. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Road America and Elkhart Lake Public Library ...
Opens in a new windowThe Esker Ridge Chalet, Pristine Elkhart Solitude
Lake Breeze on 11th

Lake Breeze on 11th

Sheboygan
Stay at this vacation home in Sheboygan. Enjoy a water park, laundry facilities, and air conditioning. Popular attractions Above & Beyond Children's Museum and ...
Opens in a new windowLake Breeze on 11th
'Twilight' - Just a few steps down to Lake Winnebago!

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

Chilton
Stay at this vacation home in Chilton. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Brothertown Harbor and The Plaid Squirrel ...
Opens in a new window'Twilight' - Just a few steps down to Lake Winnebago!
Blue Sky Country Living

Blue Sky Country Living

2 out of 5
Malone
Stay at this vacation home in Malone. Enjoy laundry facilities and air conditioning. Popular attractions Wolf Lake and Shaginappi Park are located nearby.
Opens in a new windowBlue Sky Country Living
Brick Tudor Vacation Rental House Close To Lake Michigan And Downtown

Brick Tudor Vacation Rental House Close To Lake Michigan And Downtown

Manitowoc
Stay at this vacation home in Manitowoc. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Manitowoc Family Aquatic Center and Rahr West ...
Opens in a new windowBrick Tudor Vacation Rental House Close To Lake Michigan And Downtown
East River Retreat, WATERFRONT+ Fire Pit+Pet friendly

East River Retreat, WATERFRONT+ Fire Pit+Pet friendly

Two Rivers
Stay at this vacation home in Two Rivers. Enjoy free WiFi, a garden, and patios. Popular attractions Historic Washington House and Rogers Street Fishing Village ...
Opens in a new windowEast River Retreat, WATERFRONT+ Fire Pit+Pet friendly
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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.

Sheboygan Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Sheboygan vacation homes are the perfect way for you to wing it.

Holiday houses in Sheboygan let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Sheboygan in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Sheboygan adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Sheboygan with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Sheboygan vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Sheboygan Holiday Homes essential information

Accommodation
317 Holiday Homes
Lowest Price
NZ$143
Highest Price
NZ$453
Popular accommodation
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau, Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room, New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!, The Esker Ridge Chalet, Pristine Elkhart Solitude, Lake Breeze on 11th, 'Twilight' - Just a few steps down to Lake Winnebago!, Blue Sky Country Living, Brick Tudor Vacation Rental House Close To Lake Michigan And Downtown, East River Retreat, WATERFRONT+ Fire Pit+Pet friendly

Top trending hotels in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
708 Niagara Avenue, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$220 per night from 1 Oct to 2 Oct
NZ$220
1 Oct - 2 Oct
includes taxes & fees
Book a stay at this business-friendly aparthotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Opens in a new windowGrandstay Residential Suites Hotel - Sheboygan
Quality Inn Sheboygan North I-43

Quality Inn Sheboygan North I-43

2.5 out of 5
4332 N 40th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$143 per night from 24 Sept to 25 Sept
NZ$143
24 Sept - 25 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowQuality Inn Sheboygan North I-43
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

2 out of 5
3664 S Taylor Dr, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$151 per night from 28 Sept to 29 Sept
NZ$151
28 Sept - 29 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Opens in a new windowAmericInn by Wyndham Sheboygan
Save an average of 15% on thousands of hotels when you're signed in
Watershed Hotel

Watershed Hotel

3 out of 5
838 N 15th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
The price is NZ$316 per night from 18 Sept to 19 Sept
NZ$316
18 Sept - 19 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Sheboygan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowWatershed Hotel
Don't see what you're looking for?
See all available properties in Sheboygan
View all properties
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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^Subject to availability and chosen travel dates.