Chester Holidays
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Top hotels in Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,205 reviews)
There were many good things about the stay however; our room was super close to the interstate and the traffic and trucks starting rolling by at 5:30 am. I searched for earplugs and it was not conducive to easy sleep. I would not stay again unless the room was far away from the highway. Be forewarned. ...
Reviewed on 27 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is Rp1.913.467 per night from 1 Mar to 2 Mar
Rp1.913.467
Rp2.512.364 total
1 Mar - 2 Mar
includes taxes & fees
9/10 Wonderful! (865 reviews)
Overcharged and lied to said security deposit was released back but never was
Reviewed on 26 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is Rp1.555.316 per night from 8 Mar to 9 Mar
Rp1.555.316
Rp1.737.288 total
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain.
Reviewed on 28 Feb 2026
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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