Chester Vacations
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
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Better together
Save up to ￥45,448 when you book a flight and hotel together*
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With 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
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is ￥11,677 per night from Oct 19 to Oct 20
￥11,677
￥16,343 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (646 reviews)
"Excellent location. Friendly staff."
Reviewed on Sep 17, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
The price is ￥17,480 per night from Oct 19 to Oct 20
￥17,480
￥19,831 total
Oct 19 - Oct 20
includes taxes & fees
8/10 Very Good! (1,265 reviews)
"Overall a great stay for a quick business overnight. Downfall was the shower head in bathroom had extremely low water pressure (basically non existent) and made a horrible clunking noise. Perhaps the mixing valve was broken. Found this out in morning of."
Reviewed on Sep 16, 2025
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street, West Springfield, MA
Fully refundableReserve now, pay when you stay
The price is ￥13,160 per night from Oct 1 to Oct 2
￥13,160
￥15,061 total
Oct 1 - Oct 2
includes taxes & fees
6.8/10 (1,013 reviews)
"Excellent overall!"
Reviewed on Sep 13, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
