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 ₩157,815 per night from Jan 5 to Jan 6
₩157,815
₩183,329 total
Jan 5 - Jan 6
includes taxes & fees
9.2/10 Wonderful! (2,247 reviews)
Staff and room was great
Reviewed on Jan 1, 2026
The Red Lion Inn
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is ₩216,693 per night from Jan 14 to Jan 15
₩216,693
₩306,592 total
Jan 14 - Jan 15
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!
Reviewed on Dec 26, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is ₩133,916 per night from Jan 4 to Jan 5
₩133,916
₩149,584 total
Jan 4 - Jan 5
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too!
Reviewed on Dec 28, 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.
