Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Elizabeth Massa Peroulakis
Top hotels in Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
The price is 2.717.711 ₫ per night from 7 Jan to 8 Jan
2.717.711 ₫
3.157.041 ₫ total
7 Jan - 8 Jan
includes taxes & fees
9.2/10 Wonderful! (2,249 reviews)
Clearly obvious that the American flag was not being flown daily on the center pole, by the state flag was up on the side pole!
Reviewed on 1 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundable
The price is 2.574.264 ₫ per night from 9 Jan to 10 Jan
2.574.264 ₫
2.875.452 ₫ total
9 Jan - 10 Jan
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Staff was very pleasant and friendly. From front desk to valet.
Reviewed on 1 Jan 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
Fully refundableReserve now, pay when you stay
The price is 2.052.056 ₫ per night from 21 Jan to 22 Jan
2.052.056 ₫
2.348.578 ₫ total
21 Jan - 22 Jan
includes taxes & fees
7/10 Good! (1,009 reviews)
very friendly staff, spotless room, great ameneties good location. one downside is my tv was stuck in a mode where a banner covered up a fifth of the screen every 30 seconds making watching things difficult.
Reviewed on 31 Dec 2025
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.
Popular places to visit
Chester Town Hall
You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.
