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Chesterland Holiday Rentals

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Holiday Rentals in Chesterland

Sleek DT Cleveland Apt at City Club
3.0 star property
9.4 out of 10, Exceptional, (111)
"Perfect place for us. I'll come back."
United States
Phillip
Sleek DT Cleveland Apt at City Club
2125 Superior Living
2.0 star property
6.2 out of 10, (46)
"Loved the decor, vey clean, has everything you need. Very close to downtown, just a few bus stops away. "
United States
Blanca
2125 Superior Living
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
9.6 out of 10, Exceptional, (9)
"It was fantastic couldn’t of asked for a better stay."
United States
Yarnell
The price is AU$292
includes taxes & fees
22 Oct - 23 Oct
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
Crown royal presidential suite and fitness center
8.8 out of 10, Excellent, (51)
"This place was very clean and the host responded quickly to any questions we had. "
United States
Nicole
The price is AU$186
includes taxes & fees
20 Oct - 21 Oct
Crown royal presidential suite and fitness center
Cozy Downtown Modern Condo in the Heart of it all
2.0 star property
9.6 out of 10, Exceptional, (156)
"Had a great stay. The location was perfect as we were attending the Browns game."
Canada
Tommy
The price is AU$284
includes taxes & fees
21 Oct - 22 Oct
Cozy Downtown Modern Condo in the Heart of it all
Charming 2-bedroom apartment with AC, Free Parking in wonderful Cleveland
2.0 star property
10.0 out of 10, Exceptional, (1)
"The loft is adorable with super comfy beds and a lovely. Short walk to the stadium.The owner was a gem to fix my error when I booked the wrong day. Git the place cleaned up for us on short notice and straightened everything out with vrbo.Highly recommend bith this property and renting from Liz"
United States
cynthia S.
The price is AU$265
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom apartment with AC, Free Parking in wonderful Cleveland
Luxury Downtown Townhome w/ Private Garage Unit 13
9.6 out of 10, Exceptional, (76)
"Conveniently located downtown close to bars and attractions "
Canada
Neil N.
The price is AU$269
includes taxes & fees
23 Oct - 24 Oct
Luxury Downtown Townhome w/ Private Garage Unit 13
Stylish Ohio City Retreat - Walk to West Side Market and Breweries
9.8 out of 10, Exceptional, (16)
"Great place! The owner was very accommodating and answered any communication almost immediately."
United States
Rebecca
The price is AU$259
includes taxes & fees
21 Oct - 22 Oct
Stylish Ohio City Retreat - Walk to West Side Market and Breweries
Timeless Tremont-2 Bdrm near Downtown Cle
2.0 star property
9.4 out of 10, Exceptional, (31)
"Great property, great location!!! Would stay again "
United States
Lea J.
The price is AU$311
includes taxes & fees
20 Oct - 21 Oct
Timeless Tremont-2 Bdrm near Downtown Cle
Quaint 2BR in Historical Little Italy
2.0 star property
9.0 out of 10, Wonderful, (16)
"Nice location with easy access to everything in university circle. The host was incredibly responsive with any questions we had. We had a great stay!"
United States
Daniel W.
The price is AU$241
includes taxes & fees
22 Oct - 23 Oct
Quaint 2BR in Historical Little Italy
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
10.0 out of 10, Exceptional, (69)
"We absolutely loved our stay. Location was perfect for us to take in the Feast and enjoy neighborhood, restaurants and shopping. Our host was incredible and even took the time to message me and let me know that I had left behind some perishable goodies in the refrigerator. We are in the area often and will most definitely stay here again."
United States
Trish
The price is AU$334
includes taxes & fees
21 Oct - 22 Oct
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
9.8 out of 10, Exceptional, (43)
"Nice property close to lots of restaurants. Clean and comfortable. "
United States
Thomas
The price is AU$335
includes taxes & fees
11 Nov - 12 Nov
Rare Cleveland Apt: Heart of Little Italy! With Sauna & Hot Tub!
Luxury Downtown Townhome w/ Private Garage Unit 7
9.6 out of 10, Exceptional, (15)
"This place was perfect for our stay and the garage made it so nice!"
United States
Amber D.
The price is AU$269
includes taxes & fees
23 Oct - 24 Oct
Luxury Downtown Townhome w/ Private Garage Unit 7
Cozy and Spacious 4-bedroom house in fabulous Cleveland with AC, WiFi
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay. House was very spacious and clean. Host was very nice .I would definitely recommend ."
United States
Denise G.
Cozy and Spacious 4-bedroom house in fabulous Cleveland with AC, WiFi
Luxury Downtown Townhome w/ Private Garage Unit 4
9.6 out of 10, Exceptional, (22)
"Nice, quiet and convenient location!"
United States
Lindsay D.
The price is AU$252
includes taxes & fees
20 Oct - 21 Oct
Luxury Downtown Townhome w/ Private Garage Unit 4
Charming 3-bedroom house with WiFi and AC in welcoming Cleveland
10.0 out of 10, Exceptional, (4)
"It was very nice and very spacious 10/10 "
United States
Felecia R.
The price is AU$409
includes taxes & fees
20 Oct - 21 Oct
Charming 3-bedroom house with WiFi and AC in welcoming Cleveland
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
The price is AU$242
includes taxes & fees
20 Oct - 21 Oct
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
8.6 out of 10, Excellent, (41)
"Exactly as described. Great stay! "
United States
Deborah R.
The price is AU$200
includes taxes & fees
20 Oct - 21 Oct
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Lake front park near by -15 minutes east of downtown Cleveland
The price is AU$620
includes taxes & fees
20 Oct - 21 Oct
Lake front park near by -15 minutes east of downtown Cleveland
Renovated Downtown Condo in the HEART OF IT ALL
2.0 star property
10.0 out of 10, Exceptional, (1)
"This is a great spot in nice area of town. It is perfect for a single person or a couple. Nice large windows, that open yay. Comfortable bed, great couch set up. Thanks for a great stay."
United States
Chris B.
The price is AU$286
includes taxes & fees
21 Oct - 22 Oct
Renovated Downtown Condo in the HEART OF IT ALL
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 Chesterland Hotel Reviews

Find out more about Chesterland

Everything you need to know about Chesterland 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 Chesterland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Chesterland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterland. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterland 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 Chesterland holiday rentals we have selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterland rentals

At Expedia, we put the best Chesterland 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 Chesterland 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 Chesterland 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 Chesterland. 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

Are there holiday rentals in Chesterland?

Yes, there are holiday rentals close to the most popular sights in Chesterland, or you can select a more secluded option if you're looking for a relaxing stay. Chesterland is known for its golf courses and ski areas.

What are some of the best holiday rentals that Chesterland has to offer?

Crown royal presidential suite and fitness center: This holiday home rental outside of Chesterland has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Chesterland?

Chagrin River and Chesterland City Park are a couple of lovely local spots to get outside and enjoy nature. Alpine Valley and Chester Town Hall are other places to visit while you're in town.

What are holiday rentals like in Chesterland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.