Name: Berkshires Untold
Price range: CA $109
Rating: 9

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Your Chester Vacation

Our vacation packages to Chester allow you to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this fantastic city. There's a whole load to see during a trip to Chester, including Becket Land Trust Historic Quarry and Chester Town Hall. Check out Expedia's wide range of travel options and book your ultimate vacation to Chester today.

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Chester Hotel Deals

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Fully refundableReserve now, pay when you stay

CA $170

CA $198 total

Apr 26 - Apr 27

includes taxes & fees

9.4/10 Exceptional! (2,246 reviews)

Felt safe room was clean and welcoming. Unfortunately I wasn’t able to enjoy a hot shower 2 of my 8 days. That is my one real complaint. I would suggest microwaves in room

Reviewed on Apr 12, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

CA $120

CA $165 total

May 12 - May 13

includes taxes & fees

9/10 Wonderful! (901 reviews)

Yes everything was very geared for a enjoyable time.

Reviewed on Apr 11, 2026

Berkshires Untold

194 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

CA $109

CA $121 total

Apr 14 - Apr 15

includes taxes & fees

9/10 Wonderful! (895 reviews)

We did not see a pool

Reviewed on Apr 8, 2026

See all 875 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.