Photo by Kristin DePlatchett

Chesterland Vacation Rentals

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Vacation Rentals in Chesterland

Sleek DT Cleveland Apt at City Club

3.0 star property
9.2 out of 10, Wonderful, (62)
"This was a great place to stay. Clean, spacious, and safe."
Sleek DT Cleveland Apt at City Club

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, (48)
"Great place to stay "
Barsala At The Monroe Apartments

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 vacation rentals in Chesterland?

Yes, you can find vacation rentals close to popular sights in Chesterland, or you can choose a more secluded option if you're looking for relaxation. 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 Public Library are other places to visit while you're in town.

What are vacation rentals like in Chesterland?

Vacation rentals are private properties you can book for several days or longer in Chesterland. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family gatherings.