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

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

Oostburg
With a stay at this vacation home in Oostburg, you'll be on the beach, within a 10-minute drive of Lake Michigan and Oostburg Public Library.
Large Unique & Artistic Lake Michigan Beach House / Awesome Game 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
The price is AU$598 per night from 6 Nov to 7 Nov
AU$598
includes taxes & fees
6 Nov - 7 Nov
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
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4 Bedroom Beachfront Condo - Fantastic Lake View

4 Bedroom Beachfront Condo - Fantastic Lake View

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be on the beach, within a 5-minute walk of Lake Michigan and Blue Harbor Resort & Conference Center ...
4 Bedroom Beachfront Condo - Fantastic Lake View
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

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

Sheboygan
When you stay at this vacation home in Sheboygan, you'll be on the waterfront, just steps from Lake Michigan and a 2-minute drive from St. Peter Claver ...
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!

Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!

Oostburg
With a stay at this vacation home in Oostburg, you'll be on the waterfront, within a 15-minute drive of Lake Michigan and The Bull at Pinehurst Farms Golf ...
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

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

Sheboygan
With a stay at this vacation home in Sheboygan, you'll be within a 5-minute drive of Lake Michigan and Sheboygan Indian Mound Park.
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan
The price is AU$549 per night from 6 Nov to 7 Nov
AU$549
includes taxes & fees
6 Nov - 7 Nov
With a stay at this vacation home in Sheboygan, you'll be a 1-minute walk from Lake Michigan and 6 minutes by foot from North Side Municipal Beach.
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Updated Sheboygan Home w/ Porch < 1 Mi to Beach

Updated Sheboygan Home w/ Porch < 1 Mi to Beach

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 North Side Municipal Beach.
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
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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
207 Holiday Homes
Lowest Price
AU$110
Highest Price
AU$598
Popular accommodation
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!, Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room, Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city, 4 Bedroom Beachfront Condo - Fantastic Lake View , Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!, Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!, 2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub, The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced, Updated Sheboygan Home w/ Porch < 1 Mi to Beach

Top trending hotels in Cleveland

Stunning castle with working vineyard - the ultimate luxury VRBO property!

Stunning castle with working vineyard - the ultimate luxury VRBO property!

Cleveland
With a stay at this castle in Cleveland, you'll be near the beach, within a 10-minute drive of Lake Michigan and Dairyland Park.
Stunning castle with working vineyard - the ultimate luxury VRBO property!
NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit

NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit

Cleveland
When you stay at this cottage in Cleveland, you'll be next to a golf course, just steps from Lake Michigan and a 3-minute drive from Hika Bay.
NEW! Lakeview Cottage on 3.5 acres w/hot tub and fire pit
Insane luxury beachfront estate - complete with indoor pool, arcade and theater!

Insane luxury beachfront estate - complete with indoor pool, arcade and theater!

Cleveland
When you stay at this vacation home in Cleveland, you'll be on the beach, just steps from Lake Michigan and 13 minutes by foot from Hika Bay.
Insane luxury beachfront estate - complete with indoor pool, arcade and theater!
Save an average of 15% on thousands of hotels when you're signed in
Harbor Town Inn

Harbor Town Inn

2.5 out of 5
4004 Calumet Ave., Manitowoc, WI
The price is AU$110 per night from 6 Nov to 7 Nov
AU$110
includes taxes & fees
6 Nov - 7 Nov
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
Don't see what you're looking for?
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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.