Photo by Kristin DePlatchett

Chesterland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 6 - Nov 7
Tomorrow
Nov 7 - Nov 8
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Vacation Rentals in Chesterland

Private kitchen
Sleek DT Cleveland Apt at City Club
Sleek DT Cleveland Apt at City Club
3.0 star property
9.4 out of 10, Exceptional, (113)
"Perfect place for us. I'll come back."
United States
Phillip
Sleek DT Cleveland Apt at City Club
Interior
2125 Superior Living
2125 Superior Living
2.0 star property
6.4 out of 10, (50)
"safe parking, the area is a little rough. "
United States
Richard
2125 Superior Living
Interior
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
3.0 star property
9.8 out of 10, Exceptional, (7)
"Lovely stay - comfortable studio, communicative host, great location, and easy parking. "
United States
Rachel
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
Interior
2 Mi to Zoo: Charming Apt w/ Balcony in Cleveland
2 Mi to Zoo: Charming Apt w/ Balcony in Cleveland
3.0 star property
2 Mi to Zoo: Charming Apt w/ Balcony in Cleveland
Interior
11 Mi to Dtwn Cleveland: Family Home w/ Yard
11 Mi to Dtwn Cleveland: Family Home w/ Yard
3.0 star property
11 Mi to Dtwn Cleveland: Family Home w/ Yard
Private kitchen
Cozy Getaway With Hot Tub, Patio & Fenced Yard 3 Bedroom Home
Cozy Getaway With Hot Tub, Patio & Fenced Yard 3 Bedroom Home
3.5 star property
Cozy Getaway With Hot Tub, Patio & Fenced Yard 3 Bedroom 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterland Hotel Reviews

Drury Plaza Hotel Cleveland Downtown

Drury Plaza Hotel Cleveland Downtown

10/10 Excellent
"Very nice hotel with an excellent staff."
Jeanine 2-night trip
Posted 1 day ago
Drury Plaza Hotel Cleveland Downtown

Find out more about Chesterland

Search for holiday rentals in Chesterland on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterland using one of the methods below:

  • View our selection of featured holiday rentals in Chesterland
  • Use the map to find apartments and other holiday homes in the Chesterland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterland while they last

Look no further and take a look at our great range of rental properties in Chesterland!

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. Alpine Valley and Chester Town Hall 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.