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. 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
The price is NZ$614
includes taxes & fees
26 Aug - 27 Aug
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,067 reviews)
"Great place to stay breakfast was good then room was good. Staff were great as well only issue is the pool is tiny."
United States
Devin
The price is NZ$234
includes taxes & fees
10 Sept - 11 Sept
Grandstay Residential Suites Hotel - Sheboygan

3. Lake Michigan Beachfront - King Suite - Game Room

Lake Michigan Beachfront - King Suite - Game Room
Newton
9.8 out of 10, Exceptional, (24 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$1,618
includes taxes & fees
11 Aug - 12 Aug
Lake Michigan Beachfront - King Suite - Game Room

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

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is NZ$702
includes taxes & fees
17 Aug - 18 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!

5. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is NZ$611
includes taxes & fees
11 Aug - 12 Aug
Sheboygan Riverside Condo

6. 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, (19 reviews)
"Our stay was great! Really enjoyed it!"
United States
Nic B.
The price is NZ$1,626
includes taxes & fees
11 Aug - 12 Aug
Stunning private home hidden in the woods. Can sleep 11 guests

7. 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 NZ$222
includes taxes & fees
17 Aug - 18 Aug
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

8. 4 Bedroom Home on the River with Private River access

4 Bedroom Home on the River with Private River access
Sheboygan
9.8 out of 10, Exceptional, (44 reviews)
"If you are looking for a quiet and calm place to enjoy your morning coffee or watch a sunset, this is the perfect place!"
United States
Sharon R.
The price is NZ$686
includes taxes & fees
13 Aug - 14 Aug
4 Bedroom Home on the River with Private River access

9. 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 NZ$412
includes taxes & fees
30 Aug - 31 Aug
2nd floor loft near the lake!

10. 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 NZ$718
includes taxes & fees
17 Aug - 18 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!

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, (18 reviews)
"Nice place, exactly as pictured. Enjoyed the coffee bar"
United States
Sylvia L.
The price is NZ$518
includes taxes & fees
18 Aug - 19 Aug
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

12. 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 NZ$689
includes taxes & fees
23 Aug - 24 Aug
Updated Plymouth Home ~ 5 Mi to Road America!

13. 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, (32 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is NZ$724
includes taxes & fees
17 Aug - 18 Aug
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

14. 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 NZ$674
includes taxes & fees
23 Aug - 24 Aug
Updated Plymouth Home ~ 5 Mi to Road America!

15. 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, (34 reviews)
"Great place for family to stay for wedding of grandson. "
United States
Dawn C.
The price is NZ$809
includes taxes & fees
11 Aug - 12 Aug
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

16. 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 NZ$649
includes taxes & fees
2 Sept - 3 Sept
Logan Ave Holiday House - Upper

17. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (64 reviews)
"What a perfect getaway and the host was very accommodating while respecting our privacy. We would definitely recommend!!!"
United States
Brycie K.
The price is NZ$465
includes taxes & fees
11 Aug - 12 Aug
The Esker Ridge Chalet, Pristine Elkhart Solitude

18. 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 NZ$437
includes taxes & fees
20 Aug - 21 Aug
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

19. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.0 out of 10, Very good, (6 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.
Just Beachy: 4 Bedroom, Sleeps 12!

20. 3 Min to Road America, "Amazing Location!!"

3 Min to Road America, "Amazing Location!!"
Plymouth
10.0 out of 10, Exceptional, (1 review)
"This place was perfect for our group. We were karting at Road America, and location was a little over a mile from the gate. Newly renovated and very nice. Hosts did lots of little things to add value to our stay. Plenty to do nearby. Kids loved the basement and yard, adults hung out on patio. Would definitely stay here again. "
United States
Matt W.
The price is NZ$1,413
includes taxes & fees
11 Aug - 12 Aug
3 Min to Road America, "Amazing Location!!"
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 12 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.