Chester Holidays
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Top hotels in Chester
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is S$207 per night from 7 Jul to 8 Jul
S$207
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on 23 Jun, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 15 Jul to 16 Jul
S$158
15 Jul - 16 Jul
includes taxes & fees
9.2/10 Wonderful! (2,153 reviews)
"Great place"
Reviewed on 21 Jun, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is S$205 per night from 24 Jun to 25 Jun
S$205
24 Jun - 25 Jun
includes taxes & fees
9/10 Wonderful! (997 reviews)
"Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful ..."
Reviewed on 21 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.
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