Chester Vacations
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Find the Best Chester Vacation Packages
Chester Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is ₩217,192 per night from Mar 30 to Mar 31
₩217,192
₩252,314 total
Mar 30 - Mar 31
includes taxes & fees
9.4/10 Exceptional! (2,224 reviews)
Staff was amazing! Rooms were spotless.
Reviewed on Mar 26, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩130,129 per night from Apr 26 to Apr 27
₩130,129
₩178,913 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (888 reviews)
very clean and friendly staff
Reviewed on Mar 24, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ₩104,916 per night from Mar 29 to Mar 30
₩104,916
₩117,189 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (881 reviews)
Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, ...
Reviewed on Mar 26, 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.
