Photo by Kristin DePlatchett

Chesterland Holiday Rentals

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Holiday Rentals in Chesterland

2125 Superior Living

2.0 star property
5.6 out of 10, (26)
"Great place, affordable, and close to attractions"
2125 Superior Living

Barsala At The Monroe Apartments

4.0 star property
9.2 out of 10, Wonderful, (43)
"I would definitely stay here again."
Barsala At The Monroe Apartments

Sleek DT Cleveland Apt at City Club

3.0 star property
9.2 out of 10, Wonderful, (49)
" a great experience. We would definitely stay here again. "
Sleek DT Cleveland Apt at City Club

The Abbey Apartments By Barsala

3.5 star property
8.6 out of 10, Excellent, (92)
"It was a really nice place to stay will be booking again "
The Abbey Apartments By Barsala

Gordon Square Studio ~ 4 Mi to Downtown Cleveland!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Lovely stay - comfortable studio, communicative host, great location, and easy parking. "
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
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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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 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 West Geauga Plaza 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.