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

Holiday Homes in Cleveland

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Cleveland holiday homes

A large house with a well-manicured lawn and a driveway leading to the entrance.

1. Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.2 out of 10, Wonderful, (29 reviews)
"This place is my spring spiritual reset. We’ll equipped, comfortable and serene. I had a lovely stay and hope to return next year"
United States
Kristine D.
The price is NZ$1,396
includes taxes & fees
29 Sept - 30 Sept
Lake Michigan Beachfront - King Suite - Game Room
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (14 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
The Links! - Luxury Golf Retreat with Golf Simulator
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, (42 reviews)
"Many extras that we have never seen at other rentals.Children's toys, beach toys, dog extras- leash dog bowls towels and a new toy to bring home. Walking distance to Lake Michigan. Restaurants that are 5 min distance driving. Kohler Andrae 15 min away! Kitchen had every item you would need.Hope to say again. Thanks for a great experience"
United States
Anonymous traveller
The price is NZ$740
includes taxes & fees
29 Sept - 30 Sept
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)
"The house was great! It had everything we needed, was very clean, and cozy. We enjoyed our stay and Ginger was welcoming, available, and responsive. "
United States
Christine P.
The price is NZ$415
includes taxes & fees
6 Oct - 7 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A living room with a sofa, coffee table, and TV.

5. 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, (42 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is NZ$1,062
includes taxes & fees
29 Sept - 30 Sept
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

6. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is NZ$532
includes taxes & fees
29 Sept - 30 Sept
Sheboygan Riverside Condo
A cabin with a deck, a covered porch, and a paved driveway.

7. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (70 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 NZ$484
includes taxes & fees
29 Sept - 30 Sept
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.

8. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
Two Rivers
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay."
United States
Melissa B.
The price is NZ$996
includes taxes & fees
29 Sept - 30 Sept
1 Mi to Shore: Lake Michigan Retreat w/ Game Room!
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

9. 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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is NZ$306
includes taxes & fees
7 Oct - 8 Oct
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A hotel room with two beds, a dining area, and a view of the outdoors.

10. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is NZ$308
includes taxes & fees
30 Sept - 1 Oct
Victorian Inn #241 | 2 Queen Beds
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

11. 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, (1 review)
"Just like the description. Very clean. Accommodations for kids and the host was very accommodating!"
United States
Erin S.
The price is NZ$591
includes taxes & fees
29 Sept - 30 Sept
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

12. 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 NZ$578
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
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 NZ$1,591
includes taxes & fees
29 Sept - 30 Sept
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

14. 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, (35 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
The price is NZ$842
includes taxes & fees
30 Sept - 1 Oct
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A spacious lobby with leather sofas, a chandelier, a large TV, and a foosball table.

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
8.8 out of 10, Excellent, (6 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 NZ$915
includes taxes & fees
15 Oct - 16 Oct
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
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, (17 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 NZ$1,026
includes taxes & fees
27 Oct - 28 Oct
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
A patio with a fire pit, outdoor seating, and string lights.

17. 3 Min to Road America, "Amazing Location!!"

3 Min to Road America, "Amazing Location!!"
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Great place with tons of space and updated rooms. Conveniently located for everything we did. I would absolutely recommend this place!!"
United States
Patrick F.
The price is NZ$1,455
includes taxes & fees
28 Oct - 29 Oct
3 Min to Road America, "Amazing Location!!"
A deck with a hot tub, outdoor seating, and a view of a forested area.

18. 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, (20 reviews)
"Our stay was great! Really enjoyed it!"
United States
Nic B.
The price is NZ$1,656
includes taxes & fees
29 Sept - 30 Sept
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.

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)
" 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 NZ$1,942
includes taxes & fees
2 Oct - 3 Oct
5 min from Road America. Great yard and plenty of parking
A dining area with a table, chairs, and a window with curtains.

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
The price is NZ$457
includes taxes & fees
29 Sept - 30 Sept
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
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

Lighthouse Inn

Lighthouse Inn

10/10 Excellent
"loved the location along Lake Michigan. It was a wonderful view looking over the water. Also had a very good cooked-to-order breakfast included. The pool was nice. Really enjoyed my stay."
Mary R 1-night trip
Posted 3 hours ago
Lighthouse Inn

Find out more about Cleveland

Cleveland Holiday Homes information

Number of reviews
573
Accommodation
221 Holiday Homes
Lowest Price
NZ$306
Highest Price
NZ$1,942