Chester Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
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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 ₩173,630 per night from Jan 28 to Jan 29
₩173,630
₩201,708 total
Jan 28 - Jan 29
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 ₩143,211 per night from Feb 3 to Feb 4
₩143,211
₩192,387 total
Feb 3 - Feb 4
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 ₩142,217 per night from Jan 30 to Jan 31
₩142,217
₩158,856 total
Jan 30 - Jan 31
includes taxes & fees
8/10 Very Good! (1,002 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.
