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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Cleveland holiday rentals

A spacious living area with a fireplace, a sofa, and a dining area in the background.

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,130 reviews)
"Quiet place near the lake."
United States
Vivian
The price is £89
includes taxes & fees
15 Nov - 16 Nov
Grandstay Residential Suites Hotel - Sheboygan
A narrow hallway with a bench, pillows, and a potted plant.

2. 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, (15 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is £134
includes taxes & fees
18 Nov - 19 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A wooden deck with a railing, leading to a grassy yard with trees and a clear sky.

3. Apartment Centrally Located

Apartment Centrally Located
Plymouth
10.0 out of 10, Exceptional, (2 reviews)
"Very reasonable for the price. Staff was helpful and friendly. Would definitely stay again."
United States
Russ
The price is £140
includes taxes & fees
6 Dec - 7 Dec
Apartment Centrally Located
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

4. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (30 reviews)
"Clean , quiet, great host. Property had everything we needed for a two day stay."
United States
Tim C.
The price is £157
includes taxes & fees
16 Nov - 17 Nov
2nd floor loft near the lake!
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

5. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"Great place in a great location for us."
United States
Dean M.
The price is £278
includes taxes & fees
8 Dec - 9 Dec
Sleeps 8 & Spacious!
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is £440
includes taxes & fees
12 Nov - 13 Nov
The Links! - Luxury Golf Retreat with Golf Simulator
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

7. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"We had a great time up there and the host was excellent and the property was fantastic"
United States
Alex N.
The price is £271
includes taxes & fees
8 Dec - 9 Dec
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.

8. 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, (33 reviews)
"The location was perfect to experience the Art Fair, downtown, and the area overall!Clean & comfortable - would return!"
United States
Andrea L.
The price is £272
includes taxes & fees
12 Nov - 13 Nov
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A spacious living room with a sofa, coffee table, and a TV. There is a ceiling fan, a fireplace, and a large window.

9. The Beach town bungalow

The Beach town bungalow
Sheboygan
The price is £197
includes taxes & fees
13 Nov - 14 Nov
The Beach town bungalow
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

10. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (23 reviews)
"The place was in a quiet neighborhood and a great location with easy access to everything we needed. Very clean and the host communicated everything clearly."
United States
Susan J.
The price is £247
includes taxes & fees
18 Nov - 19 Nov
Beautiful & Convenient!
A grassy yard with a mailbox, a green utility box, and a building in the background.

11. Apartment near many locations.

Apartment near many locations.
Plymouth
9.0 out of 10, Wonderful, (2 reviews)
"Surprised, pleasantly"
United States
Kevin R.
The price is £250
includes taxes & fees
9 Dec - 10 Dec
Apartment near many locations.
A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.4 out of 10, Exceptional, (41 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is £67
includes taxes & fees
30 Nov - 1 Dec
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
A deck with a view of a lake, surrounded by various signs and advertisements.

13. 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 £425
includes taxes & fees
3 Dec - 4 Dec
Victorian Inn Elkhart Lake Wisconsin
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

14. 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 £271
includes taxes & fees
6 Dec - 7 Dec
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A living room with a sofa, coffee table, and TV.

15. 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)
"Nice location and spacious."
United States
Maggie A.
The price is £424
includes taxes & fees
13 Nov - 14 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A view from a room with a sliding glass door to an outdoor deck with a wooden railing.

16. Apartment Centrally Located

Apartment Centrally Located
Plymouth
9.6 out of 10, Exceptional, (5 reviews)
"Room was as advertised, very convenient access to Road America, would stay again"
United States
Dylan C.
The price is £140
includes taxes & fees
2 Dec - 3 Dec
Apartment Centrally Located
A cozy room with a mustard-colored sofa, a wooden coffee table, and a framed painting of a market scene on the wall.

17. 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 £140
includes taxes & fees
12 Nov - 13 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A beach with pebbles, a wooden structure, and several birds.

18. 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 £241
includes taxes & fees
12 Nov - 13 Nov
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
A hallway leading to a room with a wooden floor, a white door, and a painting of sailboats on the wall.

19. 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, (12 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 £131
includes taxes & fees
15 Nov - 16 Nov
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A brick building with a wooden porch and a metal railing.

20. Apartment Centrally Located

Apartment Centrally Located
Plymouth
8.0 out of 10, Very good, (2 reviews)
The price is £140
includes taxes & fees
2 Dec - 3 Dec
Apartment Centrally Located
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

A modern interior with a stone fireplace, seating area, and a flat-screen TV mounted above it.
Watershed Hotel

Watershed Hotel

Watershed Hotel
Sheboygan

10/10 Excellent

Very clean, staff friendly & helpful. Checked in on Christmas Eve and when we opened the door on Christmas morning there was a bottle of wine and a box of biscuits outside the room. This was a very nice touch.
United Kingdom
Gaynor
Reviewed January 1, 2023
Watershed Hotel

Find out more about Cleveland

Everything you need to know about Cleveland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cleveland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cleveland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cleveland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cleveland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cleveland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cleveland holiday rentals we have selected for you start as low as £66 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cleveland rentals

At Expedia, we put the best Cleveland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cleveland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cleveland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cleveland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.