Name: The Yankee, Trademark Collection by Wyndham
Price range: CA $134
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 $141

CA $164 total

Feb 8 - Feb 9

includes taxes & fees

9.2/10 Wonderful! (2,238 reviews)

Clean, safe, quiet, and comfortable. Fantastic full breakfast as always.

Reviewed on Feb 6, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

CA $135

CA $181 total

Feb 8 - Feb 9

includes taxes & fees

9/10 Wonderful! (825 reviews)

We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ...

Reviewed on Feb 1, 2026

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

CA $134

CA $150 total

Feb 8 - Feb 9

includes taxes & fees

9/10 Wonderful! (1,010 reviews)

The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay.

Reviewed on Feb 5, 2026

See all 849 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.