Chester Holidays
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Top hotels in Chester
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is €125 per night from 6 Jul to 7 Jul
€125
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"The hot tub was welcomed after a long day of hiking the Berkshires!"
Reviewed on 26 Jun 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundable
The price is €96 per night from 13 Jul to 14 Jul
€96
13 Jul - 14 Jul
includes taxes & fees
7/10 Good! (1,001 reviews)
"Room was nice. Bed ok. Price was good."
Reviewed on 25 Jun 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is €157 per night from 27 Jul to 28 Jul
€157
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. ..."
Reviewed on 26 Jun 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.
Stay near popular Chester attractions
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