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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £89 per night from 24 May to 25 May
£89
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (925 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on 4 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £93 per night from 14 May to 15 May
£93
14 May - 15 May
includes taxes & fees
9/10 Wonderful! (932 reviews)
Easy, comfortable and convenient; rooms and public spaces are nice, modern and stylish updates of modest 60s/70s original motel facilities.
Reviewed on 6 May 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is £140 per night from 27 May to 28 May
£140
27 May - 28 May
includes taxes & fees
9.2/10 Wonderful! (2,219 reviews)
The room was massive and roomy. The floor was shiny and clean. Everything was tidy. The bed and pillows were comfortable.
Reviewed on 6 May 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.
