Holiday Homes in Cleveland

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Cabins
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Apartments
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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Cleveland holiday homes

A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

1. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is AU$291
includes taxes & fees
16 Nov - 17 Nov
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

2. 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, (43 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 AU$519
includes taxes & fees
6 Dec - 7 Dec
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A modern living room with a sofa, two chairs, a coffee table, a ceiling fan, and a large window with curtains.

3. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great location, centrally located, clean and well-furnished. Ginger was a great host, very accommodating."
United States
Tonja K.
The price is AU$292
includes taxes & fees
16 Nov - 17 Nov
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

4. The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is AU$857
includes taxes & fees
15 Nov - 16 Nov
The Links! - Luxury Golf Retreat with Golf Simulator
A resort with a pool, beach, and multiple buildings surrounded by trees.

5. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is AU$254
includes taxes & fees
15 Nov - 16 Nov
Victorian Inn #241 | 2 Queen Beds
An outdoor seating area with a view of a lake, surrounded by trees and a barbecue grill.

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

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Two Rivers
10.0 out of 10, Exceptional, (50 reviews)
"So delightful and a wonderful stay!"
United States
Tom & Jenny S.
The price is AU$362
includes taxes & fees
19 Nov - 20 Nov
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
A beach with pebbles, a wooden structure, and several birds.

7. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place. The owners were very helpful during our stay with recommendations on things to do as our fishing trip was cancelled!"
United States
Nicole B.
The price is AU$471
includes taxes & fees
29 Nov - 30 Nov
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Beach

8. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 reviews)
"Property was clean and the check in process was smooth. Right on the beach which was fantastic!"
United States
Sherrill S.
The price is AU$913
includes taxes & fees
14 Nov - 15 Nov
Beachfront Paradise: King Suite - Sleeps 8!
A modern kitchen with white cabinetry and a dining area with a white table and chairs.

9. Road America, Elkhart Lake!

Road America, Elkhart Lake!
Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is AU$526
includes taxes & fees
8 Dec - 9 Dec
Road America, Elkhart Lake!
A living room with a sofa, coffee table, and TV.

10. 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
9.8 out of 10, Exceptional, (43 reviews)
"Nice location and spacious."
United States
Maggie A.
The price is AU$822
includes taxes & fees
15 Nov - 16 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A cabin with a deck, a covered porch, and a paved driveway.

11. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (73 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is AU$432
includes taxes & fees
17 Nov - 18 Nov
The Esker Ridge Chalet, Pristine Elkhart Solitude
A room with a wooden ceiling, large windows, and a seating area with two chairs and a table.

12. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.6 out of 10, Exceptional, (15 reviews)
"Great place for book club"
United States
Kelly S.
The price is AU$790
includes taxes & fees
19 Nov - 20 Nov
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

13. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (18 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is AU$1,466
includes taxes & fees
15 Nov - 16 Nov
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

14. 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, (151 reviews)
"Quiet place to just get away."
United States
Cheryl
The price is AU$203
includes taxes & fees
16 Nov - 17 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A black sports car parked in front of a building with a Shell gas station sign.

15. 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
9.0 out of 10, Wonderful, (7 reviews)
"This is an amazing and fun property. If you are in town for any event at Road America it makes it a little more special."
United States
Ryan K.
The price is AU$683
includes taxes & fees
14 Nov - 15 Nov
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

16. 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, (36 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
The price is AU$657
includes taxes & fees
30 Nov - 1 Dec
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

17. 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
9.8 out of 10, Exceptional, (19 reviews)
"Everything was amazing and if we come back next year we will be staying again"
United States
Cristy
The price is AU$797
includes taxes & fees
15 Nov - 16 Nov
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

18. 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, (182 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is AU$516
includes taxes & fees
5 Dec - 6 Dec
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
A bedroom with a bed, a desk, a ceiling fan, a TV, and a wardrobe.

19. Stunning private home hidden in the woods. Can sleep 11 guests

Stunning private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was great! Really enjoyed it!"
United States
Nic B.
The price is AU$1,490
includes taxes & fees
15 Nov - 16 Nov
Stunning private home hidden in the woods. Can sleep 11 guests
A grassy outdoor area with a wooden deck, a small shed, and a green hose coiled on the ground.

20. 5 min from Road America. Great yard and plenty of parking

5 min from Road America. Great yard and plenty of parking
Elkhart Lake
9.8 out of 10, Exceptional, (8 reviews)
"My family and I enjoyed a wonderful night in this beautiful family friendly home. All adminities were perfect. Everybody had a great time and I really appreciated. Thank you very much. I/We would recommend this place and this renter to anybody!!! Also, hoping to meet up with him again next year. Again thank you!Joan"
United States
Joan B.
The price is AU$2,011
includes taxes & fees
27 Nov - 28 Nov
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.
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Learn more about Cleveland

Nestled along Lake Michigan's shores, this charming village invites visitors to hike scenic trails at Fischer Creek State Recreation Area. Spend sunny afternoons at North Side Municipal Beach before exploring Hika Bay and the peaceful grounds of Veterans Memorial Park.

See all hotels in Cleveland
A rocky shoreline with waves crashing against the rocks and a large weeping willow tree in the background.

Top reviews in Cleveland

A spacious dining area with white chairs and tables, large windows with blinds, and a view of the outdoors.
Harbor Town, BW Signature Collection

Harbor Town, BW Signature Collection

Harbor Town, BW Signature Collection
Manitowoc

10/10 Excellent

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Australia
Maree
Reviewed October 20, 2024
Harbor Town, BW Signature Collection