Book Holiday Homes in Cleveland

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Featured Holiday Homes in Cleveland

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

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

Waldo
Located in Waldo, this vacation home is within a 15-minute drive of Evergreen Golf Course and Sheboygan County Fairgrounds.
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

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

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be near the beach, within a 10-minute walk of Lake Michigan and Above & Beyond Children's Museum.
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

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

Elkhart Lake
With a stay at this vacation home in Elkhart Lake, you'll be within a 10-minute drive of Road America and Farmers Market.
Elkhart Lake, WI home close to lake, downtown, and Road America racetrack
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NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area

NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be on a lake, just steps from Lake Michigan and 11 minutes by foot from James Tellen Woodland Sculpture ...
NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area
Lake Michigan Gem: Private Beach & Game Room

Lake Michigan Gem: Private Beach & Game Room

Newton
With a stay at this vacation home in Newton, you'll be on the waterfront, within a 10-minute drive of Lake Michigan and Fischer Creek State Recreation Area.
Lake Michigan Gem: Private Beach & Game Room
Lake Breeze on 11th

Lake Breeze on 11th

Sheboygan
With a stay at this vacation home in Sheboygan, you'll be within a 5-minute drive of Lake Michigan and Aurora Sheboygan Memorial Medical Center.
Lake Breeze on 11th
Cozy Cape Cod Home

Cozy Cape Cod Home

Plymouth
With a stay at this vacation home in Plymouth, you'll be within a 15-minute drive of Road America and Sheboygan County Fairgrounds.
Cozy Cape Cod Home
The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude

Elkhart Lake
With a stay at this vacation home in Elkhart Lake, you'll be within a 10-minute drive of Road America and Farmers Market.
The Esker Ridge Chalet, Pristine Elkhart Solitude
Private Beach on Lake Michigan: Oostburg Home

Private Beach on Lake Michigan: Oostburg Home

Oostburg
With a stay at this vacation home in Oostburg, you'll be on the beach, within a 15-minute drive of Lake Michigan and Whispering Pines Amphitheater.
Private Beach on Lake Michigan: Oostburg Home
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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.

Cleveland 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 Cleveland vacation homes are the perfect way for you to wing it.

Holiday houses in Cleveland 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 Cleveland 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 Cleveland adventures, obvs.

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

Cleveland Holiday Homes essential information

Accommodation
257 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
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, Elkhart Lake, WI home close to lake, downtown, and Road America racetrack, NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area, Lake Michigan Gem: Private Beach & Game Room, Lake Breeze on 11th, Cozy Cape Cod Home, The Esker Ridge Chalet, Pristine Elkhart Solitude, Private Beach on Lake Michigan: Oostburg Home

Top trending hotels in Cleveland

Harbor Town Inn

Harbor Town Inn

2.5 out of 5
4004 Calumet Ave., Manitowoc, WI
Located in Manitowoc, Harbor Town Inn is in the business district, a 4-minute drive from Wisconsin Maritime Museum and 5 minutes from Rahr West Art Museum.
Harbor Town Inn
Quality Inn

Quality Inn

2.5 out of 5
4332 N 40th St, Sheboygan, WI
Fully refundableReserve now, pay when you stay
With a stay at Quality Inn in Sheboygan, you'll be within a 10-minute drive of Lake Michigan and Aurora Sheboygan Memorial Medical Center.
Quality Inn
Lighthouse Inn

Lighthouse Inn

2.5 out of 5
1515 Memorial Dr, Two Rivers, WI
Fully refundableReserve now, pay when you stay
With a stay at Lighthouse Inn, you'll be centrally located in Two Rivers, steps from Lake Michigan and within a 10-minute walk of Lester Public Library.
Lighthouse Inn
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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
With a stay at AmericInn by Wyndham Sheboygan in Sheboygan, you'll be in a shopping district, within a 10-minute drive of Lake Michigan and Deer Trace Mall.
AmericInn by Wyndham Sheboygan
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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.

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^Subject to availability and chosen travel dates.