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
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is £121 per night from 7 Jul to 8 Jul
£121
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on 23 Jun 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is £92 per night from 15 Jul to 16 Jul
£92
15 Jul - 16 Jul
includes taxes & fees
9.2/10 Wonderful! (2,153 reviews)
"Great place"
Reviewed on 21 Jun 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is £135 per night from 23 Jul to 24 Jul
£135
23 Jul - 24 Jul
includes taxes & fees
9/10 Wonderful! (997 reviews)
"Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful ..."
Reviewed on 21 Jun 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.
