Chester Holidays
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Your Chester Holiday
Our holiday packages to Chester allow you to create your own adventure. Tailor your getaway to your needs and interests and make every moment count in this fantastic city. There's a whole load to see during a trip to Chester, including Becket Land Trust Historic Quarry and Chester Town Hall. Check out Expedia's wide range of travel options and book your ultimate holiday to Chester today.
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 | Blandford Ski Area, Maple Corner Farm Cross Country Ski Area and Chester Town Hall |
Top hotels in Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is £94 per night from 30 Mar to 31 Mar
£94
30 Mar - 31 Mar
includes taxes & fees
9.4/10 Exceptional! (2,220 reviews)
The staff were very friendly, making the entire stay pleasant from check-in to check-out. The hotel was clean and well-maintained, and the surroundings were quiet, which made it easy to relax. The room was also quite spacious, providing plenty of comfort during the stay. It’s a great choice for anyone ...
Reviewed on 23 Mar 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £92 per night from 30 Mar to 31 Mar
£92
30 Mar - 31 Mar
includes taxes & fees
9/10 Wonderful! (885 reviews)
very clean and friendly staff
Reviewed on 24 Mar 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £58 per night from 1 Apr to 2 Apr
£58
1 Apr - 2 Apr
includes taxes & fees
9/10 Wonderful! (880 reviews)
Wonderful place, great toiletries and great friendly staff. We will be back
Reviewed on 22 Mar 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
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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. Flight-inclusive packages are ATOL protected.
