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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Cleveland vacation homes

A resort with a pool, beach, and multiple buildings surrounded by trees.

1. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is ￥16,059
￥28,645 total
includes taxes & fees
Oct 31 - Nov 1
Victorian Inn #241 | 2 Queen Beds
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.

2. 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 ￥23,666
￥42,441 total
includes taxes & fees
Oct 31 - Nov 1
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.

3. 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 ￥18,459
￥60,885 total
includes taxes & fees
Nov 9 - Nov 10
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A dining table with a vase of green leaves and a candle.

4. 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, (8 reviews)
"We stayed a very short time due to many wedding details and festivities and the stay was just what we needed. Convenient to wedding location, very clean, comfy beds, friendly and reliable host! Would highly recommend!"
United States
Stephanie M.
The price is ￥17,039
￥34,203 total
includes taxes & fees
Nov 1 - Nov 2
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A modern living room with a sofa, two chairs, a coffee table, a ceiling fan, and a large window with curtains.

5. 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 ￥19,708
￥37,401 total
includes taxes & fees
Nov 4 - Nov 5
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.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (15 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is ￥35,474
￥96,452 total
includes taxes & fees
Nov 1 - Nov 2
The Links! - Luxury Golf Retreat with Golf Simulator
An outdoor seating area with a view of a lake, surrounded by trees and a barbecue grill.

7. 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 ￥15,608
￥38,295 total
includes taxes & fees
Nov 2 - Nov 3
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
A modern living room with a sofa, armchair, and ottoman, a dining area with a table and chairs, and a kitchen with a refrigerator and cabinets.

8. Beach Escape w/ Hot Tub & Fire Pit

Beach Escape w/ Hot Tub & Fire Pit
Two Rivers
10.0 out of 10, Exceptional, (4 reviews)
"Nice location, good parking, great host."
United States
Clark L.
The price is ￥19,550
￥82,337 total
includes taxes & fees
Nov 2 - Nov 3
Beach Escape w/ Hot Tub & Fire Pit
A beach with pebbles, a wooden structure, and several birds.

9. 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 ￥41,622
￥54,041 total
includes taxes & fees
Nov 5 - Nov 6
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
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)
"Great place close to everything we needed. Walking distance to the coffee shop, beach, bar, and pizza place. Not much more you really need."
United States
Gregory D.
The price is ￥49,663
￥95,200 total
includes taxes & fees
Nov 8 - Nov 9
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, (71 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 ￥31,374
￥43,246 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥23,334
￥91,442 total
includes taxes & fees
Nov 2 - Nov 3
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, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is ￥90,339
￥168,209 total
includes taxes & fees
Nov 5 - Nov 6
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A black sports car parked in front of a building with a Shell gas station sign.

14. 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 ￥41,859
￥79,092 total
includes taxes & fees
Nov 5 - Nov 6
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

15. 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, (150 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥19,879
￥24,301 total
includes taxes & fees
Nov 9 - Nov 10
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

16. 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 ￥30,223
￥90,600 total
includes taxes & fees
Oct 31 - Nov 1
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.

17. 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, (181 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is ￥31,926
￥52,811 total
includes taxes & fees
Nov 6 - Nov 7
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

18. 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 ￥47,298
￥76,014 total
includes taxes & fees
Nov 4 - Nov 5
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A grassy outdoor area with a wooden deck, a small shed, and a green hose coiled on the ground.

19. 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 ￥101,170
￥159,998 total
includes taxes & fees
Oct 31 - Nov 1
5 min from Road America. Great yard and plenty of parking
A deck with a hot tub, outdoor seating, and a view of a forested area.

20. 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 ￥126,128
￥152,027 total
includes taxes & fees
Oct 31 - Nov 1
Stunning private home hidden in the woods. Can sleep 11 guests
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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Top Cleveland Hotel Reviews

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

8/10 Good
"We would stay there again. Clean, decent breakfast and right off the highway. We even enjoyed the hot tub after a long day in Green Bay!"
Craig 1-night trip
Posted 7 hours ago
Comfort Inn & Suites Sheboygan I-43

Find out more about Cleveland

Cleveland Vacation Homes information

Number of reviews
605
Accommodation
222 Vacation Homes
Lowest Price
￥24,301
Highest Price
￥168,209