Chester Holidays
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Chester Holiday
Our pick of the best Chester Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is NZ$248 per night from 26 Apr to 27 Apr
NZ$248
26 Apr - 27 Apr
includes taxes & fees
9.4/10 Exceptional! (2,220 reviews)
Very nice place.
Reviewed on 29 Mar 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 28 Apr to 29 Apr
NZ$207
28 Apr - 29 Apr
includes taxes & fees
9/10 Wonderful! (888 reviews)
very clean and friendly staff
Reviewed on 24 Mar 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$136 per night from 1 Apr to 2 Apr
NZ$136
1 Apr - 2 Apr
includes taxes & fees
9/10 Wonderful! (883 reviews)
I spent 2 lovely nights here on my way through the Berkshires. Everyone was so kind, helpful and professional. Flatbread was delicious and a cup of tea in the cozy fire nook was perfect.
Reviewed on 28 Mar 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.