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 ₩171,118 per night from Jan 19 to Jan 20
₩171,118
₩198,784 total
Jan 19 - Jan 20
includes taxes & fees
9.2/10 Wonderful! (2,225 reviews)
Yes
Reviewed on Jan 13, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩145,076 per night from Feb 2 to Feb 3
₩145,076
₩194,892 total
Feb 2 - Feb 3
includes taxes & fees
9/10 Wonderful! (810 reviews)
Very comfortable and very close to ski slope and restaurants
Reviewed on Jan 10, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ₩144,070 per night from Jan 23 to Jan 24
₩144,070
₩160,932 total
Jan 23 - Jan 24
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...
Reviewed on Jan 7, 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.
