Name: Holiday Inn & Suites Pittsfield-Berkshires by IHG
Price range: AU$164
Rating: 8

Photo by Elizabeth Massa Peroulakis

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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

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Fully refundableReserve now, pay when you stay

AU$202

12 Jan - 13 Jan

includes taxes & fees

9.2/10 Wonderful! (2,261 reviews)

The staff was super helpful and courteous. The room and public areas were superb. We did not use the pool but the area was neatly kept and very attractive (brightly colored and well lit). The hotel is located in a safe area, surrounded by woods, and overlooking the Connecticut River.

Reviewed on 6 Jan 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

AU$198

1 Feb - 2 Feb

includes taxes & fees

9/10 Wonderful! (807 reviews)

I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights.

Reviewed on 5 Jan 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Fully refundable

AU$164

23 Jan - 24 Jan

includes taxes & fees

8/10 Very Good! (1,001 reviews)

Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...

Reviewed on 7 Jan 2026

See all 833 properties in Chester

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.