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

Cleveland Holiday Rentals

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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 rentals

A hotel room with a bed, two bedside tables, a lamp, a chair, and a painting on the wall.

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,097 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is HK$942
HK$1,069 total
includes taxes & fees
1 Nov - 2 Nov
Grandstay Residential Suites Hotel - Sheboygan
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 cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

3. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (28 reviews)
"The location was amazing and the place is really nice! Absolutely love that it is dog friendly and the host is really responsive! We will definitely be staying again! "
United States
Emily G.
The price is HK$1,154
HK$1,942 total
includes taxes & fees
12 Oct - 13 Oct
2nd floor loft near the lake!
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

4. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
Logan Ave Holiday House - Upper
A spacious living area with a wooden dining table, chairs, and a sofa. There is a staircase leading to another level, and a large window providing natural light.

5. Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is HK$798
HK$2,046 total
includes taxes & fees
14 Oct - 15 Oct
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

6. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is HK$848
HK$1,657 total
includes taxes & fees
5 Oct - 6 Oct
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A living room with a sofa, coffee table, and TV.

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, (42 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is HK$2,472
HK$4,703 total
includes taxes & fees
5 Oct - 6 Oct
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A fire pit surrounded by four light blue chairs in a grassy outdoor area.

8. Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
9.8 out of 10, Exceptional, (10 reviews)
"Close to everything we were looking to do while visiting the area. Great communication and hospitality from host, would stay again!!"
United States
Heidi
The price is HK$746
HK$1,523 total
includes taxes & fees
2 Nov - 3 Nov
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

9. 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 HK$1,201
HK$3,394 total
includes taxes & fees
26 Oct - 27 Oct
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A deck with a view of a lake, surrounded by various signs and advertisements.

10. Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
The price is HK$1,272
HK$5,436 total
includes taxes & fees
11 Oct - 12 Oct
Victorian Inn Elkhart Lake Wisconsin
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.

11. 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
9.8 out of 10, Exceptional, (19 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is HK$628
HK$1,425 total
includes taxes & fees
6 Oct - 7 Oct
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
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.

12. 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 HK$3,916
HK$7,544 total
includes taxes & fees
5 Oct - 6 Oct
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A bathroom with white shelves holding wicker baskets and a potted plant.

13. Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
9.8 out of 10, Exceptional, (8 reviews)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is HK$902
HK$1,719 total
includes taxes & fees
1 Nov - 2 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

14. 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 HK$2,072
HK$2,690 total
includes taxes & fees
13 Oct - 14 Oct
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Beach

15. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
6.8 out of 10, (5 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."
United States
Nina S.
The price is HK$1,530
HK$5,097 total
includes taxes & fees
5 Oct - 6 Oct
Beachfront Paradise: King Suite - Sleeps 8!
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

Harbor Town, BW Signature Collection

Harbor Town, BW Signature Collection

10/10 Excellent
"Clean especially for an older hotel."
RYAN 1-night trip
Posted 7 hours ago
Harbor Town, BW Signature Collection

Find out more about Cleveland

Search for holiday rentals in Cleveland on Expedia! You can easily find your home rentals, villas, holiday apartments in Cleveland using one of the methods below:

  • View our selection of featured holiday rentals in Cleveland
  • Use the map to find apartments and other holiday homes in the Cleveland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cleveland while they last

Look no further and take a look at our great range of rental properties in Cleveland!

Frequently asked questions

Can I find a holiday rental in Cleveland?

Yes, there are holiday rentals close to the most popular sights in Cleveland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cleveland has to offer?

Insane luxury beachfront estate - complete with indoor pool, arcade and theater!: This highly rated holiday home rental in Cleveland is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cleveland?

Expedia has 10 holiday rentals for your stay in Cleveland.

What can I see and do in Cleveland?

Lake Michigan and Dairyland Park are a couple of lovely local spots to get outside and enjoy nature. While here, Veterans Memorial Park and Hika Bay are other places worth a visit.

What are holiday rentals like in Cleveland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cleveland. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for family trips.