Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$703 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
Your Chester Holiday
The lively city of Chester is calling. Uncover both its hidden gems and highlights with a Chester holiday package that's tailored to you. Chester Town Hall and Becket Land Trust Historic Quarry are some of the major attractions to check out during a trip to Chester. No matter your travel plans or budget, putting together the ultimate tailored Chester holiday is a walk in the park with Expedia.
Chester Holiday
Chester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 630 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Maple Corner Farm Cross Country Ski Area, Blandford Ski Area and Chester Town Hall |
Our pick of the best Chester Hotel Deals
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 21 Apr to 22 Apr
AU$199
21 Apr - 22 Apr
includes taxes & fees
9.4/10 Exceptional! (2,258 reviews)
Housekeeping was hit or miss, one day they changed out towels, did not make the bed. Another day they did both. Unsure. Room was sandy so no sweeping done. Both the heater and the fireplace were incredibly loud, the heater making ticking noises that kept waking me up. Overall, the stay was fine. ...
Reviewed on 14 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 19 Apr to 20 Apr
AU$159
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (906 reviews)
Clean, hot shower. Great pressure
Reviewed on 14 Apr 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 30 Apr to 1 May
AU$122
30 Apr - 1 May
includes taxes & fees
9/10 Wonderful! (899 reviews)
Perfect
Reviewed on 16 Apr 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
