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Check prices for these dates

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul
In one month
31 Jul - 2 Aug
In two months
28 Aug - 30 Aug

Our top choices for Chester lodges

Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,005 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is AED 491
AED 630 total
includes taxes & fees
2 Aug - 3 Aug
Berkshire Mountain Lodge
Property grounds

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington
10.0 out of 10, Exceptional, (3 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
United States
Mary D.
The price is AED 400
AED 501 total
includes taxes & fees
5 Jul - 6 Jul
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (996 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is AED 685
AED 765 total
includes taxes & fees
20 Jul - 21 Jul
Berkshires Untold
Property grounds

Historic, Waterfront Suite Rental close to Boston, Massachusetts

Historic, Waterfront Suite Rental close to Boston, Massachusetts
Cummington
The price is AED 400
AED 501 total
includes taxes & fees
5 Jul - 6 Jul
Historic, Waterfront Suite Rental close to Boston, Massachusetts
Property grounds

Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts

Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts
Cummington
The price is AED 400
AED 501 total
includes taxes & fees
5 Jul - 6 Jul
Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts
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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Top Chester Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical fare: eggs, cereal, yogurt, fresh fruit, bread/pastries, etc. As we were there for only one night, we did not take advantage of the outdoor pool or fire pit, but both appeared to be clean and well maintained."
Gail 1-night trip
Posted less than an hour ago
The Yankee Inn

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