Chester Holidays

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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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 14 June to 15 June
AU$220
14 June - 15 June
includes taxes & fees
9/10 Wonderful! (960 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"

Reviewed on 28 May 2026

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
Fully refundable
The price is AU$145 per night from 29 June to 30 June
AU$145
29 June - 30 June
includes taxes & fees
7/10 Good! (1,003 reviews)
"Clean comfortable rooms, balcony views, staff was nice and helpful, very clean good smelling"

Reviewed on 31 May 2026

Quality Inn West Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 14 June to 15 June
AU$156
14 June - 15 June
includes taxes & fees
9.2/10 Wonderful! (2,194 reviews)
"Very nice"

Reviewed on 31 May 2026

D. Hotel Suites & Spa
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.