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

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Our top choices for Cleveland vacation homes

1. 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 AED 430
AED 1,347 total
includes taxes & fees
9 Nov - 10 Nov
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

2. 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, (9 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 AED 551
AED 942 total
includes taxes & fees
3 Dec - 4 Dec
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

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

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (16 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is AED 864
AED 2,094 total
includes taxes & fees
15 Nov - 16 Nov
The Links! - Luxury Golf Retreat with Golf Simulator

5. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is AED 374
AED 634 total
includes taxes & fees
3 Nov - 4 Nov
Victorian Inn #241 | 2 Queen Beds

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

7. 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 AED 1,286
AED 2,264 total
includes taxes & fees
30 Nov - 1 Dec
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

8. 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 AED 970
AED 1,196 total
includes taxes & fees
3 Dec - 4 Dec
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

9. 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 AED 455
AED 1,822 total
includes taxes & fees
3 Nov - 4 Nov
Beach Escape w/ Hot Tub & Fire Pit

10. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (72 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 AED 812
AED 1,054 total
includes taxes & fees
15 Nov - 16 Nov
The Esker Ridge Chalet, Pristine Elkhart Solitude

11. 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 AED 975
AED 1,750 total
includes taxes & fees
3 Nov - 4 Nov
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

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 AED 544
AED 2,026 total
includes taxes & fees
3 Nov - 4 Nov
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

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 AED 2,105
AED 3,635 total
includes taxes & fees
3 Nov - 4 Nov
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

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, (150 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is AED 514
AED 589 total
includes taxes & fees
3 Dec - 4 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

15. 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.
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

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 AED 736
AED 2,044 total
includes taxes & fees
3 Nov - 4 Nov
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

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, (182 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is AED 744
AED 1,230 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

18. 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 AED 2,879
AED 4,138 total
includes taxes & fees
6 Nov - 7 Nov
5 min from Road America. Great yard and plenty of parking

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 AED 2,938
AED 3,209 total
includes taxes & fees
14 Nov - 15 Nov
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