Chester Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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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 ₩175,071 per night from Jan 27 to Jan 28
₩175,071
₩203,382 total
Jan 27 - Jan 28
includes taxes & fees
9.2/10 Wonderful! (2,245 reviews)
Friendly staff. Enjoy the homey feel, different from the cookie cutter box feel of chains.
Reviewed on Jan 24, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ₩144,400 per night from Feb 1 to Feb 2
₩144,400
₩193,984 total
Feb 1 - Feb 2
includes taxes & fees
9/10 Wonderful! (818 reviews)
Great kitchen! Helpful staff, very convenient location.
Reviewed on Jan 21, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ₩143,398 per night from Jan 30 to Jan 31
₩143,398
₩160,176 total
Jan 30 - Jan 31
includes taxes & fees
8/10 Very Good! (1,001 reviews)
generally good
Reviewed on Jan 19, 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.
