Photo by Elizabeth Massa Peroulakis

Search Chalets in Chester

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare Chalets in Chester with updated reviews, rates, and availability.

Little Longbow Lakefront Chalet
Golf
Little Longbow Lakefront Chalet
10.0 out of 10, Exceptional, (4)
"House is well kept and very clean. Pretty view. Quiet and calm area to relax in, wish we had more days here. Very good WIFI and flat screens also."
Little Longbow Lakefront Chalet
Sunny Chalet Nestled in the Woods of Ashfield
Interior
Sunny Chalet Nestled in the Woods of Ashfield
9.8 out of 10, Exceptional, (10)
"We enjoyed the area and the home. Hannah was very responsive!"
Sunny Chalet Nestled in the Woods of Ashfield
Private Berkshires Hilltop Retreat w Magic View, 1mi to Lake Garfield Beach
Main level open space (old setup)
Private Berkshires Hilltop Retreat w Magic View, 1mi to Lake Garfield Beach
9.8 out of 10, Exceptional, (21)
"Beautiful well kept house in the Berkshires, great view and layout. Close to amazing nature and Great Barrington if you need anything. Wonderful trip!"
Private Berkshires Hilltop Retreat w Magic View, 1mi to Lake Garfield Beach
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Nature retreat by Brook
Rustic contemporary with field stone foyer and working fireplace
Nature retreat by Brook
Nature retreat by Brook
Don't see what you're looking for?
See all available properties in Chester
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.

Other property types in Chester

Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required
Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
Cozy apartment located in quiet Williamsburg
Exterior
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (35)
"Very clean and nice apartment in a pleasant little city."
The price is AED 551
AED 955 total
includes taxes & fees
17 Jun - 18 Jun
Cozy apartment located in quiet Williamsburg
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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.

Recent reviews of Chester hotels
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

5/5 Excellent
Great place to stay!
"Friendly check in experience. Greeted us with a warm welcome. "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Springfield MA
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Springfield MA