Chester Vacations
Book a Hotel + Flight or Car together to unlock savings
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- 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
- Rest easyPlan, book, and manage your trip all in one place
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 ₩168,261 per night from Jan 11 to Jan 12
₩168,261
₩195,463 total
Jan 11 - Jan 12
includes taxes & fees
9.2/10 Wonderful! (2,262 reviews)
The staff was super helpful and courteous. The room and public areas were superb. We did not use the pool but the area was neatly kept and very attractive (brightly colored and well lit). The hotel is located in a safe area, surrounded by woods, and overlooking the Connecticut River.
Reviewed on Jan 6, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ₩136,104 per night from Jan 10 to Jan 11
₩136,104
₩152,028 total
Jan 10 - Jan 11
includes taxes & fees
8/10 Very Good! (1,007 reviews)
Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN
Reviewed on Jan 4, 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundableReserve now, pay when you stay
The price is ₩111,693 per night from Feb 1 to Feb 2
₩111,693
₩127,833 total
Feb 1 - Feb 2
includes taxes & fees
7/10 Good! (1,009 reviews)
very friendly staff, spotless room, great ameneties good location. one downside is my tv was stuck in a mode where a banner covered up a fifth of the screen every 30 seconds making watching things difficult.
Reviewed on Dec 31, 2025
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.
