Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 4 Chalets in Chester with updated reviews, rates, and availability.

Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
3 bedrooms, desk, iron/ironing board, travel crib

Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach

9.8 out of 10, Exceptional, (23)
"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
Sunny Chalet Nestled in the Woods of Ashfield
Interior

Sunny Chalet Nestled in the Woods of Ashfield

9.4 out of 10, Exceptional, (15)
"Great spot for a friends' getaway! The house is spacious with a bright, big living room perfect for gatherings. The location is stunning, nestled in a beautiful area with a hiking trail right in the backyard. Plus, there are interesting places to visit nearby like Historic Deerfield and Shelburne Falls. The only downside was some machinery noise from the first floor, especially at night. Overall, a lovely stay!"
Sunny Chalet Nestled in the Woods of Ashfield
Little Longbow Lakefront Chalet
Smart TV, fireplace

Little Longbow Lakefront Chalet

9.2 out of 10, Wonderful, (10)
"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "
Little Longbow Lakefront Chalet
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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Other property types in Chester

The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is AED 437
AED 570 total
includes taxes & fees
5 Jun - 6 Jun
Deluxe Queen Room with 2 Queen Beds
Cozy Home in Holyoke with 2 bedrooms
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 2 bedrooms

10.0 out of 10, Exceptional, (4)
"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "
The price is AED 595
AED 1,210 total
includes taxes & fees
19 May - 20 May
Cozy Home in Holyoke with 2 bedrooms
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.