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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Cleveland holiday rentals

Lobby

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,071 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is HK$997
HK$1,131 total
includes taxes & fees
1 Sept - 2 Sept
Grandstay Residential Suites Hotel - Sheboygan
1 bedroom, WiFi

2. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.6 out of 10, Exceptional, (30 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is HK$745
HK$1,024 total
includes taxes & fees
19 Aug - 20 Aug
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
TV

3. Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great place to stay, the area is safe and close to the Marina. Owner/host was excellent to communicate with."
United States
Mary A.
The price is HK$1,075
HK$3,331 total
includes taxes & fees
18 Aug - 19 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
Interior

4. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is HK$863
HK$2,930 total
includes taxes & fees
19 Aug - 20 Aug
Sleeps 8 & Spacious!
Interior

5. Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is HK$1,420
HK$3,246 total
includes taxes & fees
18 Aug - 19 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
Exterior

6. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.8 out of 10, Exceptional, (6 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is HK$1,106
HK$2,859 total
includes taxes & fees
15 Sept - 16 Sept
Logan Ave Holiday House - Upper
Smart TV

7. 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, (18 reviews)
"Nice place, exactly as pictured. Enjoyed the coffee bar"
United States
Sylvia L.
The price is HK$1,169
HK$2,129 total
includes taxes & fees
18 Aug - 19 Aug
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Coffee/tea maker, fridge, microwave, oven

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (11 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 price is HK$1,766
HK$4,836 total
includes taxes & fees
31 Aug - 1 Sept
The Links! - Luxury Golf Retreat with Golf Simulator
Smart TV, books

9. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (21 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is HK$863
HK$2,636 total
includes taxes & fees
24 Aug - 25 Aug
Beautiful & Convenient!
Interior

10. 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$975
HK$1,676 total
includes taxes & fees
18 Aug - 19 Aug
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Living area

11. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (24 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$1,951 total
includes taxes & fees
30 Aug - 31 Aug
2nd floor loft near the lake!
Smart TV

12. 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, (34 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is HK$1,412
HK$3,278 total
includes taxes & fees
23 Aug - 24 Aug
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
3 bedrooms, iron/ironing board, travel cot, WiFi

13. 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, (9 reviews)
"We enjoyed our stay and found the place very comfortable for our family of five. It was easy to walk down to see the lake and a quick drive to restaurants in town."
United States
Amanda
The price is HK$895
HK$1,568 total
includes taxes & fees
14 Sept - 15 Sept
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Dining

14. 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, (24 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is HK$918
HK$2,209 total
includes taxes & fees
8 Sept - 9 Sept
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Interior

15. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
The price is HK$1,514
HK$3,117 total
includes taxes & fees
23 Aug - 24 Aug
Updated Plymouth Home ~ 5 Mi to Road America!
Exterior

16. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (65 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 HK$1,562
HK$2,161 total
includes taxes & fees
18 Aug - 19 Aug
The Esker Ridge Chalet, Pristine Elkhart Solitude
3 bedrooms, desk, iron/ironing board, travel cot

17. Sleeps 7{SPACIOUS}Pets Welcome!

Sleeps 7{SPACIOUS}Pets Welcome!
Sheboygan
9.4 out of 10, Exceptional, (3 reviews)
"Great location and amenities. Would definitely book again!"
United States
Elizabeth S.
The price is HK$975
HK$2,782 total
includes taxes & fees
14 Sept - 15 Sept
Sleeps 7{SPACIOUS}Pets Welcome!
Interior

18. 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
10.0 out of 10, Exceptional, (6 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$1,083
HK$1,817 total
includes taxes & fees
19 Aug - 20 Aug
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Dining

19. 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 HK$1,177
HK$1,933 total
includes taxes & fees
14 Sept - 15 Sept
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Coffee/tea maker, fridge, microwave, stovetop

20. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
The price is HK$1,161
HK$3,196 total
includes taxes & fees
23 Aug - 24 Aug
Updated Plymouth Home ~ 5 Mi to Road America!
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

8/10 Good
"The property was good, but the toilet had a ring and smell to the bathroom."
Mang 1-night trip
Posted 14 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 11 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.