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 £88 per night from 10 Feb to 11 Feb
£88
10 Feb - 11 Feb
includes taxes & fees
9.2/10 Wonderful! (2,232 reviews)
Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back
Reviewed on 31 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is £98 per night from 8 Feb to 9 Feb
£98
8 Feb - 9 Feb
includes taxes & fees
9/10 Wonderful! (827 reviews)
Room was clean and nicely equipped with kitchen. Will return if the future.
Reviewed on 1 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is £81 per night from 9 Feb to 10 Feb
£81
9 Feb - 10 Feb
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
Room was reasonably comfortable and always nice to be looking out at the mountain. Staff is always pleasant and efficient. Very good value for the money.
Reviewed on 3 Feb 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.
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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.
