Chesterfield Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$134 when you book a flight and hotel together*
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Top hotels in Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (744 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you
Reviewed on 2 Nov, 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is S$133 per night from 16 Nov to 17 Nov
S$133
16 Nov - 17 Nov
includes taxes & fees
7/10 Good! (1,041 reviews)
Everything was okay I think just slightly overpriced
Reviewed on 2 Nov, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
The price is S$143 per night from 21 Nov to 22 Nov
S$143
21 Nov - 22 Nov
includes taxes & fees
7.8/10 Good! (938 reviews)
Spotless and friendly staff
Reviewed on 2 Nov, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
