Find holiday rentals that suit your style
Apartments
Aparthotels
Our top choices for Cleveland holiday homes
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 4Sheboygan
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
Brian L.
The price is HK$698
HK$1,433 total
includes taxes & fees
27 Nov - 28 Nov
2. The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully FencedSheboygan
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."
Jean S.
The price is HK$883
HK$2,827 total
includes taxes & fees
6 Dec - 7 Dec
3. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Eclectic Artsy 3-bedroom house with King Bed & AC in SheboyganSheboygan
10.0 out of 10, Exceptional, (1 review)
"Great location, centrally located, clean and well-furnished. Ginger was a great host, very accommodating."
Tonja K.
4. The Links! - Luxury Golf Retreat with Golf Simulator
The Links! - Luxury Golf Retreat with Golf SimulatorSheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Perfect trip and great location"
Kristian N.
The price is HK$1,845
HK$4,595 total
includes taxes & fees
9 Dec - 10 Dec
5. Victorian Inn #241 | 2 Queen Beds
Victorian Inn #241 | 2 Queen BedsElkhart Lake
The price is HK$799
HK$1,354 total
includes taxes & fees
17 Nov - 18 Nov
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!"
Tom & Jenny S.
The price is HK$776
HK$1,914 total
includes taxes & fees
23 Nov - 24 Nov
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 ChairSheboygan
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!"
Nicole B.
The price is HK$2,070
HK$2,555 total
includes taxes & fees
15 Nov - 16 Nov
8. Beachfront Paradise: King Suite - Sleeps 8!
Beachfront Paradise: King Suite - Sleeps 8!Sheboygan
7.0 out of 10, Good, (6 reviews)
"It was ok but it was the second year in a row that we did not get condo we rented due to a "door lock" issue."
Nina S.
The price is HK$1,529
HK$4,871 total
includes taxes & fees
13 Nov - 14 Nov
9. Road America, Elkhart Lake!
Road America, Elkhart Lake!Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is HK$1,467
HK$2,883 total
includes taxes & fees
8 Dec - 9 Dec
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 citySheboygan
9.8 out of 10, Exceptional, (43 reviews)
"Nice location and spacious."
Maggie A.
The price is HK$2,470
HK$4,495 total
includes taxes & fees
13 Nov - 14 Nov
11. The Esker Ridge Chalet, Pristine Elkhart Solitude
The Esker Ridge Chalet, Pristine Elkhart SolitudeElkhart 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!!"
Barbara
The price is HK$1,561
HK$2,027 total
includes taxes & fees
1 Dec - 2 Dec
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"
Kelly S.
The price is HK$1,161
HK$4,175 total
includes taxes & fees
18 Nov - 19 Nov
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! "
Brad T.
The price is HK$4,494
HK$7,958 total
includes taxes & fees
23 Nov - 24 Nov
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."
Cheryl
The price is HK$988
HK$1,142 total
includes taxes & fees
18 Nov - 19 Nov
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 KohlerKiel
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."
Ryan K.
The price is HK$2,082
HK$3,562 total
includes taxes & fees
22 Nov - 23 Nov
16. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road AmericaReedsville
9.8 out of 10, Exceptional, (36 reviews)
"Our 4th time here. Great stay as always."
Jason R.
The price is HK$2,354
HK$3,427 total
includes taxes & fees
16 Nov - 17 Nov
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 PlymouthPlymouth
9.8 out of 10, Exceptional, (19 reviews)
"Everything was amazing and if we come back next year we will be staying again"
Cristy
The price is HK$1,572
HK$4,365 total
includes taxes & fees
12 Nov - 13 Nov
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!"
Doug S.
The price is HK$1,765
HK$2,838 total
includes taxes & fees
6 Dec - 7 Dec
19. Stunning private home hidden in the woods. Can sleep 11 guests
Stunning private home hidden in the woods. Can sleep 11 guestsPlymouth
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was great! Really enjoyed it!"
Nic B.
The price is HK$7,058
HK$8,084 total
includes taxes & fees
13 Nov - 14 Nov
20. 5 min from Road America. Great yard and plenty of parking
5 min from Road America. Great yard and plenty of parkingElkhart 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"
Joan B.
The price is HK$8,041
HK$11,008 total
includes taxes & fees
27 Nov - 28 Nov
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.
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.
