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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Our top choices for Cleveland holiday rentals

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,127 reviews)
"Quiet place near the lake."
United States
Vivian
The price is NZ$246
includes taxes & fees
9 Nov - 10 Nov
Grandstay Residential Suites Hotel - Sheboygan

2. 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 NZ$330
includes taxes & fees
2 Dec - 3 Dec
Apartment Centrally Located

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (16 reviews)
"Perfect trip and great location"
United States
Kristian N.
The price is NZ$1,073
includes taxes & fees
9 Nov - 10 Nov
The Links! - Luxury Golf Retreat with Golf Simulator

4. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"It suited our needs. Interior lighting was a bit harsh"
United States
James
The price is NZ$644
includes taxes & fees
9 Nov - 10 Nov
Sleeps 8 & Spacious!

5. 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 NZ$390
includes taxes & fees
9 Nov - 10 Nov
2nd floor loft near the lake!

6. 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 NZ$607
includes taxes & fees
6 Dec - 7 Dec
Apartment near many locations.

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 NZ$574
includes taxes & fees
8 Dec - 9 Dec
Logan Ave Holiday House - Upper

8. 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)
"Great place close to everything we needed. Walking distance to the coffee shop, beach, bar, and pizza place. Not much more you really need."
United States
Gregory D.
The price is NZ$1,028
includes taxes & fees
13 Nov - 14 Nov
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

9. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (23 reviews)
"Wonderful property! Communication was wonderful and so very helpful at all times. Not far from the marina, where we spent a lot of our time. "
United States
Susan G.
The price is NZ$583
includes taxes & fees
9 Nov - 10 Nov
Beautiful & Convenient!

10. 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 NZ$668
includes taxes & fees
9 Nov - 10 Nov
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

11. 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 NZ$312
includes taxes & fees
9 Nov - 10 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

12. 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 NZ$330
includes taxes & fees
2 Dec - 3 Dec
Apartment Centrally Located

13. 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, (40 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is NZ$139
includes taxes & fees
10 Nov - 11 Nov
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

14. 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 NZ$1,031
includes taxes & fees
9 Nov - 10 Nov
Victorian Inn Elkhart Lake Wisconsin

15. 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 NZ$312
includes taxes & fees
9 Nov - 10 Nov
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

16. 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 NZ$644
includes taxes & fees
6 Dec - 7 Dec
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

17. Apartment Centrally Located

Apartment Centrally Located
Plymouth
8.0 out of 10, Very good, (2 reviews)
The price is NZ$330
includes taxes & fees
6 Dec - 7 Dec
Apartment Centrally Located

18. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.6 out of 10, Excellent, (8 reviews)
"The condo was very clean and comfortable. It was just steps from the lake. It's a great place to stay!"
United States
Erika M.
The price is NZ$1,402
includes taxes & fees
9 Nov - 10 Nov
Just Beachy: 4 Bedroom, Sleeps 12!

19. Edgewater Villa: 4 Bedroom, Sleeps 14!

Edgewater Villa: 4 Bedroom, Sleeps 14!
Sheboygan
8.2 out of 10, Very good, (18 reviews)
"Nice property, close to the beach. It was perfect for our weekend getaway. "
United States
Rebecca B.
The price is NZ$1,402
includes taxes & fees
9 Nov - 10 Nov
Edgewater Villa: 4 Bedroom, Sleeps 14!

20. 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."
United States
Nina S.
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

Find out more about Cleveland

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cleveland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cleveland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cleveland. Seeing all the best attractions is bound to make you fall in love with Cleveland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cleveland short-term rentals, that won’t be hard to do.

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.