Chesterland Holiday Rentals

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Our top choices for Chesterland holiday rentals

9.4 out of 10, Exceptional, (13 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
The price is AU$260
includes taxes & fees
25 Jan - 26 Jan
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
3.0 star property
8.0 out of 10, Very good, (2 reviews)
"Great location and neighborhood. Very close to JCU. Went to a concert at the stadium and it worked out great. Host was great with communication and no issues. "
United States
Amy
The price is AU$331
includes taxes & fees
22 Jan - 23 Jan
9 Mi to Cleveland: Home Near Hospitals & Colleges
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful experience! The bed was very comfortable and the space was beautiful and clean. We enjoyed how quiet the area was and it was perfect for our weekend getaway. We will absolutely be staying here the next time we are out this way!"
United States
Ashley
The price is AU$282
includes taxes & fees
25 Jan - 26 Jan
Peaceful private apartment in the charming Hiram countryside
9.8 out of 10, Exceptional, (27 reviews)
"We absolutely loved this place ! "
United States
Celeste K.
The price is AU$232
includes taxes & fees
22 Jan - 23 Jan
Nice Apartment next to Christmas Story House
9.4 out of 10, Exceptional, (3 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is AU$250
includes taxes & fees
22 Jan - 23 Jan
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
10.0 out of 10, Exceptional, (1 review)
"The property is amazing, as is the cabin. Love the decor. We appreciated the privacy, the hot tub worked great. We also appreciated the fire ring with everything needed to build a fire! We had a lovely visit with a great friend, daughter, and her grandson that live in the area. Thanks for everything!"
United States
Jeannie
The price is AU$250
includes taxes & fees
26 Jan - 27 Jan
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Condo in Downtown Cleveland

10th Floor Downtown High-Rise Gym
2.0 star property
9.6 out of 10, Exceptional, (4 reviews)
"Amazing stay! Perfect location, very clean, and plenty of space. The host was quick to respond and extremely helpful, which made everything smooth and stress-free. Highly recommend!"
United States
Angelina
The price is AU$268
includes taxes & fees
22 Jan - 23 Jan
10th Floor Downtown High-Rise Gym
9.6 out of 10, Exceptional, (15 reviews)
"Nice, clean place in a great location. "
United States
John S.
The price is AU$379
includes taxes & fees
2 Feb - 3 Feb
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed
9.8 out of 10, Exceptional, (61 reviews)
"Great location. Host was very responsive. This unit is comfortable, well stocked and was perfect for our trip to Cleveland Clinic!"
United States
Anonymous traveller
The price is AU$239
includes taxes & fees
22 Jan - 23 Jan
Classic near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
10.0 out of 10, Exceptional, (48 reviews)
"Had a great stay here while in Cleveland for a concert. Clean, comfortable, and great location. Would definitely stay again if in the area! "
United States
Ashley F.
The price is AU$227
includes taxes & fees
22 Jan - 23 Jan
Crisp 2 bedroom upstairs apartment in historic duplex
2.5 star property
10.0 out of 10, Exceptional, (1 review)
"Room was very spacious and clean. Check in and check out instructions were easy to follow. The location was just perfect too. The athletic club on the 12th floor was clean and easily accessible and the building was full of history! Highly recommend, will be coming back!"
United States
Jason
The price is AU$287
includes taxes & fees
26 Jan - 27 Jan
Luxe Flat w/ Heated Pool & Sauna • Gym•Heart of DT
9.0 out of 10, Wonderful, (32 reviews)
"Clean, very comfortable bed, and great location+dining options!"
United States
Noah
The price is AU$218
includes taxes & fees
22 Jan - 23 Jan
Cozy CLE: Enjoy 15% Off 3+ Jan Nights! Easy Access to Clinic, Case, Downtown!

Holiday Home in Middlefield

Little house on the farm
10.0 out of 10, Exceptional, (94 reviews)
"My stay here was wonderful! James and Anna were very welcoming and such a clean place when arriving! I love this area as I grew up here and was close to many destinations I had planned. I will definitely be returning again."
United States
Sarah S.
The price is AU$336
includes taxes & fees
24 Jan - 25 Jan
Little house on the farm

Apartment in Willowick

Residential Apartment w/Drumkit
10.0 out of 10, Exceptional, (18 reviews)
"Great, quiet place! "
United States
Ranae K.
The price is AU$243
includes taxes & fees
22 Jan - 23 Jan
Residential Apartment w/Drumkit
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Everything was handled very well re: reservation, check-in, check-out. Accommodation was excellent, location in a great part of Cleveland. Had a great experience!"
United States
Stephen E.
The price is AU$192
includes taxes & fees
22 Jan - 23 Jan
Dwntwn Luxe Suite Rock Hall • Casino • Stadiums

Holiday Home in Northfield

Acadia Farms Carriage House
10.0 out of 10, Exceptional, (2 reviews)
"Clean room, beautiful grounds, well equipped kitchen, great location for dog walks! Perfect for our family of four!"
United States
Natalie
The price is AU$297
includes taxes & fees
22 Jan - 23 Jan
Acadia Farms Carriage House

Holiday Home in Downtown Cleveland

Luxury Downtown Townhome w/ Private Garage Unit 7
9.6 out of 10, Exceptional, (18 reviews)
"This place was perfect for our stay and the garage made it so nice!"
United States
Amber D.
The price is AU$259
includes taxes & fees
10 Feb - 11 Feb
Luxury Downtown Townhome w/ Private Garage Unit 7

Holiday Home in Downtown Cleveland

Luxury Downtown Townhome w/ Private Garage Unit 3
9.8 out of 10, Exceptional, (23 reviews)
"Nice townhouse, walking distance to downtown. The garage parking is nice to have. Will stay there again."
United States
Sonny C.
The price is AU$243
includes taxes & fees
22 Jan - 23 Jan
Luxury Downtown Townhome w/ Private Garage Unit 3
10.0 out of 10, Exceptional, (12 reviews)
"Great property in a great location. "
United States
Susan K.
The price is AU$299
includes taxes & fees
25 Jan - 26 Jan
Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.
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?

Luxury Downtown Townhome w/ Private Garage Unit 4: This holiday home rental outside of Chesterland is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. Fowler's Mill Golf Course and Alpine Valley 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.