Photo by Kristin DePlatchett

Search Cottages in Chesterland

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

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Cottages in Chesterland

Exterior detail
Country Cottage Farm Stay at Stoneycreek Acres
Country Cottage Farm Stay at Stoneycreek Acres
10.0 out of 10, Exceptional, (69)
"Second time staying here in two years. The cottage is perfect for some relaxing, slow time with the wife. Molly is probably the best host we have had at a vrbo"
United States
Douglas G.
The price is AED 694
AED 1,208 total
includes taxes & fees
31 Oct - 1 Nov
Country Cottage Farm Stay at Stoneycreek Acres
Exterior
Historic Cleveland Heights Carriage House!
Historic Cleveland Heights Carriage House!
9.6 out of 10, Exceptional, (43)
"Love this place. Stayed here before and will continue when visiting Cleveland"
United States
Robert and Paula G.
The price is AED 716
AED 1,507 total
includes taxes & fees
28 Oct - 29 Oct
Historic Cleveland Heights Carriage House!
Terrace/patio
Vineyard View | Walk to Wineries & River| Hot Tub
Vineyard View | Walk to Wineries & River| Hot Tub
10.0 out of 10, Exceptional, (62)
"Loved this property! Had everything you needed. Beautiful and so clean. We had the best time! The host was very helpful and replied very fast. "
United States
Payton S.
The price is AED 1,047
AED 1,707 total
includes taxes & fees
2 Nov - 3 Nov
Vineyard View | Walk to Wineries & River| Hot Tub
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

The Westin Cleveland Downtown

The Westin Cleveland Downtown

10/10 Excellent
"Very nice"
Will 1-night trip
Posted 1 day ago
The Westin Cleveland Downtown

Frequently asked questions

Why book your cottage in Chesterland with Expedia?
Booking a cottage in Chesterland is as simple as entering your travel dates and choosing an ideal place for outdoor recreation and relaxation. From ritzy retreats to affordable stays and cottages that feature conveniences like a kitchen, Expedia has something for all tastes. As for unbeatable deals? We've got them as well!
How can I find cheap cottages in Chesterland?
The easiest way to compare cheap cottages in Chesterland is with Expedia's handy filter tool. Narrow your search by star rating, amenities and budget to snag unbeatable prices with only a few clicks.