Chester Packages (Flight + Hotel)
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- Better togetherSave up to ฿4,531 when you book a flight and hotel together*
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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
9.4/10 Exceptional! (2,207 reviews)
The room was beautiful peaceful and I loved the hot tub.
Reviewed on 1 Mar 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿3,539 per night from 2 Mar to 3 Mar
฿3,539
฿4,646 total
2 Mar - 3 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 ฿2,876 per night from 8 Mar to 9 Mar
฿2,876
฿3,213 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
