Search Holiday Homes in Cleveland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Cleveland holiday homes

Smart TV

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Sheboygan
10.0 out of 10, Exceptional, (13 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is £124
includes taxes & fees
2 Mar - 3 Mar
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Children’s area

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

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (122 reviews)
"Our host was warm and welcoming and our accommodations were wonderful (well appointed and decorated … every detail well thought out)."
United States
Heidi E.
The price is £110
includes taxes & fees
4 Mar - 5 Mar
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Interior

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Plymouth
9.6 out of 10, Exceptional, (10 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
The price is £425
includes taxes & fees
2 Mar - 3 Mar
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Fridge, microwave, oven, stovetop

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

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (40 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is £285
includes taxes & fees
2 Mar - 3 Mar
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Smart TV

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
10.0 out of 10, Exceptional, (24 reviews)
"Great location!! Super clean, all we needed "
United States
Kathy P.
The price is £309
includes taxes & fees
5 Mar - 6 Mar
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Living area

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Ellis Historical District
9.6 out of 10, Exceptional, (12 reviews)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is £117
includes taxes & fees
2 Mar - 3 Mar
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Exterior detail

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Reedsville
9.8 out of 10, Exceptional, (32 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is £357
includes taxes & fees
2 Mar - 3 Mar
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is £202
includes taxes & fees
4 Mar - 5 Mar
The Esker Ridge Chalet, Pristine Elkhart Solitude
Dining

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Sheboygan
10.0 out of 10, Exceptional, (6 reviews)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Exterior detail

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (173 reviews)
"Great place would go back"
United States
William
The price is £241
includes taxes & fees
12 Mar - 13 Mar
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Exterior

Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.8 out of 10, Exceptional, (17 reviews)
" Great location! Enjoyed the sunrises. "
United States
Barb S.
The price is £517
includes taxes & fees
3 Mar - 4 Mar
Lake Michigan Beachfront - King Suite - Game Room
Fridge, microwave, oven, stovetop

The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (8 reviews)
"If I could give it higher than 5 stars I would. Property was spotless, like new, great communication with owner, very easy check in/check out process, website doesn't do it justice. Will definitely rent again on our next trip to the area."
United States
Frank V.
The Links! - Luxury Golf Retreat with Golf Simulator
Interior

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Kiel
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful place! "
United States
Colleen & Mark G.
The price is £454
includes taxes & fees
13 Mar - 14 Mar
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Interior

Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
Sheboygan Riverside Condo
Terrace/patio

Beautiful private home hidden in the woods. Can sleep 11 guests

Beautiful private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"Very clean and private property! "
United States
sherine m.
The price is £708
includes taxes & fees
4 Mar - 5 Mar
Beautiful private home hidden in the woods. Can sleep 11 guests
Fridge, microwave, oven, stovetop

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (12 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is £588
includes taxes & fees
1 Mar - 2 Mar
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Dining

Road America, Elkhart Lake!

Road America, Elkhart Lake!
Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is £275
includes taxes & fees
4 Mar - 5 Mar
Road America, Elkhart Lake!
TV

This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.

This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.
Elkhart Lake
10.0 out of 10, Exceptional, (3 reviews)
"Gorgeous house with everything you need and just a block away from RA"
United States
Hiroshi W.
The price is £885
includes taxes & fees
1 Mar - 2 Mar
This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.
Property grounds

5 min from Road America. Great yard and plenty of parking

5 min from Road America. Great yard and plenty of parking
Elkhart Lake
10.0 out of 10, Exceptional, (2 reviews)
" We enjoyed our stay very much. The house is lovely, spacious, and clean. The property is quite big and provides an excellent space to walk or room for younger children to play. Several family members enjoyed a walk about after our drive on Saturday. The house was perfect for our group, and the living room was our gathering place for Saturday evening as well as Sunday morning. We cooked our evening meal and our morning breakfast in the kitchen. The only minor issue was that our group had 9...
United States
Paul & Jacqleene M.
The price is £997
includes taxes & fees
1 Mar - 2 Mar
5 min from Road America. Great yard and plenty of parking
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.
View all properties

The Annual Holiday Sale

Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cleveland Hotel Reviews

Shoreline Serenity - 2 Private Acres

Shoreline Serenity - 2 Private Acres

10/10 Excellent
"This was the loveliest place to stay! Erin was so communicative beforehand and our stay far exceeded expectations. Anything and everything you could ask for. The mattresses were so comfortable! Lots of extra touches from toiletries to snacks- this place really has it all. (If only Mother Nature would’ve got the memo that weekend about being hospitable). We had breakfast in Sheboygan Field to Fork and dinner in Manitowoc at Waterfront Wine Bar. Both within 20 minutes and excellent. Thank you to our excellent hosts! We look forward to a return trip in nicer weather! "
Leslie H. 2-night trip
Posted 2 days ago
Shoreline Serenity - 2 Private Acres

Find out more about Cleveland

Cleveland Holiday Homes information

Number of reviews
533
Accommodation
230 Holiday Homes
Lowest Price
£110
Highest Price
£997