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Cleveland Holiday Rentals

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Our top choices for Cleveland holiday rentals

1. Spacious 4-Bedroom 3 Acre Fence County Home in Cleveland MO!

Spacious 4-Bedroom 3 Acre Fence County Home in Cleveland MO!
Cleveland
10.0 out of 10, Exceptional, (27 reviews)
"Excellent stay!!"
United States
Shelle S.
The price is NZ$478
includes taxes & fees
3 Sept - 4 Sept
Spacious 4-Bedroom 3 Acre Fence County Home in Cleveland MO!

2. New Conestoga 1843 Wagon

New Conestoga 1843 Wagon
Peculiar
10.0 out of 10, Exceptional, (58 reviews)
"Loved everything! Everyone was super nice, lots of privacy."
United States
Ann Marie Y.
The price is NZ$381
includes taxes & fees
2 Sept - 3 Sept
New Conestoga 1843 Wagon

3. New Cabin for an Adventure

New Cabin for an Adventure
Peculiar
9.6 out of 10, Exceptional, (20 reviews)
"This was a very clean and nice place to stay. The cabin was located about 30 minutes outside of KC so the travel wasnt bad for our weekend vacation. "
United States
Benjamin W.
The price is NZ$482
includes taxes & fees
23 Sept - 24 Sept
New Cabin for an Adventure

4. Pilot's Pad Studio on 75 Acres + Fishing Pond

Pilot's Pad Studio on 75 Acres + Fishing Pond
Pleasant Hill
9.6 out of 10, Exceptional, (13 reviews)
"We really enjoyed our stay! The place was perfect! "
United States
Eric M.
The price is NZ$396
includes taxes & fees
22 Sept - 23 Sept
Pilot's Pad Studio on 75 Acres + Fishing Pond

5. Clean, spacious, and fully renovated townhouse with modern charm and comfort.

Clean, spacious, and fully renovated townhouse with modern charm and comfort.
Spring Hill
9.8 out of 10, Exceptional, (42 reviews)
"This place is really clean and nicely updated. The nice large smart TV and comfortable living room furniture and bed made the stay very enjoyable. Way better than a hotel room."
United States
Scott & Tara F.
The price is NZ$379
includes taxes & fees
30 Aug - 31 Aug
Clean, spacious, and fully renovated townhouse with modern charm and comfort.

6. Beautiful, spacious, clean house for families #2

Beautiful, spacious, clean house for families #2
Stanley
9.0 out of 10, Wonderful, (24 reviews)
"Property was clean and in a great area of KC. Excelllent host."
United States
Oupekha P.
The price is NZ$466
includes taxes & fees
30 Aug - 31 Aug
Beautiful, spacious, clean house for families #2

7. Charming Family Retreat South Overland Park

Charming Family Retreat South Overland Park
Overland Park
9.2 out of 10, Wonderful, (29 reviews)
"Amazing location with easy access to shopping and food, great value, amazing responsive host who is very accommodating. Would recommend to anyone trying to stay in the greater KC area "
United States
Elias B.
The price is NZ$554
includes taxes & fees
30 Aug - 31 Aug
Charming Family Retreat South Overland Park

8. Peaceful Pondside Stay

Peaceful Pondside Stay
Archie
8.0 out of 10, Very good, (4 reviews)
"Stay was great and host communicated very well. The wifi was not working or was wrong but that wasn't the end of the world for us.Overall, it was a great stay. We just stayed overnight but area was clean and stay was enjoyable. Nice little place to relax."
United States
Jerry F.
The price is NZ$295
includes taxes & fees
14 Sept - 15 Sept
Peaceful Pondside Stay

9. Cozy Guest Suite with Fireplace & Private Entrance

Cozy Guest Suite with Fireplace & Private Entrance
Grandview
9.4 out of 10, Exceptional, (60 reviews)
"Nice place to stay."
United States
Tim M.
The price is NZ$244
includes taxes & fees
14 Sept - 15 Sept
Cozy Guest Suite with Fireplace & Private Entrance

10. 10 Minutes to the Stadiums

10 Minutes to the Stadiums
South Kansas City
9.6 out of 10, Exceptional, (17 reviews)
"Overall we had a really good stay here. It was very cute and clean, as well as a perfect space for two people!"
United States
Sydney H.
The price is NZ$185
includes taxes & fees
31 Aug - 1 Sept
10 Minutes to the Stadiums

11. WaterWalk Extended Stay by Wyndham Kansas City - Overland Pk

WaterWalk Extended Stay by Wyndham Kansas City - Overland Pk
3.5 star property
Overland Park
9.2 out of 10, Wonderful, (1,177 reviews)
"It’s always a great place to stay."
United States
Michelle
The price is NZ$234
includes taxes & fees
7 Sept - 8 Sept
WaterWalk Extended Stay by Wyndham Kansas City - Overland Pk

12. Cozy Stay_ 4BR_ Near HWY Access_ All King Beds !

Cozy Stay_ 4BR_ Near HWY Access_ All King Beds !
Grandview
10.0 out of 10, Exceptional, (1 review)
"Unassuming quiet neighborhood with friendly neighbors and shopping close enough to walk. You will find open space and large old trees that provide brilliant shade in the summer. The house is fantastic. Fresh, clean, well cared for and with subtle touches that make a rental feel like home. Well-stocked, conversational decor, and perfect for relaxing in the living room or getting time to yourself in the bedrooms.Exceptionally communicative and kind owners.If you work with mobility issues, this...
United States
Nicole G.
Cozy Stay_ 4BR_ Near HWY Access_ All King Beds !

13. The Cottage at BluHawk Farms

The Cottage at BluHawk Farms
Overland Park
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stay, very out of the way. "
United States
Dan N.
The price is NZ$391
includes taxes & fees
1 Sept - 2 Sept
The Cottage at BluHawk Farms

14. Cozy Ranch Home with Relaxed Small-Town Feel

Cozy Ranch Home with Relaxed Small-Town Feel
Spring Hill
9.8 out of 10, Exceptional, (7 reviews)
"This was a perfect quick stop for a night on our way home from a long trip. We got a good nights rest. "
United States
Heather R.
The price is NZ$401
includes taxes & fees
14 Sept - 15 Sept
Cozy Ranch Home with Relaxed Small-Town Feel

15. Boho Beauty Newly Remodled 4BD/3 FULL BATH

Boho Beauty Newly Remodled 4BD/3 FULL BATH
Overland Park
10.0 out of 10, Exceptional, (75 reviews)
"Wonderful place to stay! "
United States
Nolan & Chelsea F.
Boho Beauty Newly Remodled 4BD/3 FULL BATH

16. Comfy, Spacious & Convinient 3/2 house in Overland Park

Comfy, Spacious & Convinient 3/2 house in Overland Park
Overland Park
9.4 out of 10, Exceptional, (28 reviews)
"We had a great stay and would definitely stay there again! "
United States
Rebecca M.
The price is NZ$515
includes taxes & fees
30 Aug - 31 Aug
Comfy, Spacious & Convinient 3/2 house in Overland Park

17. Overland Park Downtown | Comfy, Clean & Safe house on Hardy

Overland Park Downtown | Comfy, Clean & Safe house on Hardy
Overland Park
9.8 out of 10, Exceptional, (40 reviews)
"Nice location and well equipped kitchen. "
United States
Paul H.
The price is NZ$500
includes taxes & fees
2 Sept - 3 Sept
Overland Park Downtown | Comfy, Clean & Safe house on Hardy

18. Historic Charm: Spacious 4BR Retreat Sleeps 11

Historic Charm: Spacious 4BR Retreat Sleeps 11
Grandview
The price is NZ$686
includes taxes & fees
31 Aug - 1 Sept
Historic Charm: Spacious 4BR Retreat Sleeps 11

19. Spacious and comfortable 3 bedrooms house in the heart of Overland Park

Spacious and comfortable 3 bedrooms house in the heart of Overland Park
Overland Park
9.4 out of 10, Exceptional, (37 reviews)
"We are very happy with our staying."
United States
Simon S.
The price is NZ$446
includes taxes & fees
30 Aug - 31 Aug
Spacious and comfortable 3 bedrooms house in the heart of Overland Park

20. Family and Large Group Friendly Suburb Home!

Family and Large Group Friendly Suburb Home!
Overland Park
9.8 out of 10, Exceptional, (51 reviews)
"Wonderful place for a family reunion"
United States
Amy D.
The price is NZ$913
includes taxes & fees
31 Aug - 1 Sept
Family and Large Group Friendly Suburb Home!
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

Are there holiday rentals 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?

Comfortable Olathe Getaway 3 Bedrooms - Sleeps 6: This holiday home rental outside of Cleveland is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay.

How many holiday rentals are there in Cleveland?

Expedia has 3 holiday rentals for your stay in Cleveland.

What can I see and do in Cleveland?

Explore the area and family-friendly sights such as Belton Grandview and Kansas City Railroad and Museum, or get out into nature at a spot like Overland Park Arboretum and Botanical Gardens. Louisburg Cider Mill and Iron Horse Golf Course are a couple of places you'll find in the wider area.

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 offer amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.