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 2.719.780 ₫ per night from 6 Jan to 7 Jan
2.719.780 ₫
3.159.446 ₫ total
6 Jan - 7 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 2.576.224 ₫ per night from 9 Jan to 10 Jan
2.576.224 ₫
2.877.642 ₫ 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 2.058.088 ₫ per night from 1 Feb to 2 Feb
2.058.088 ₫
2.355.481 ₫ total
1 Feb - 2 Feb
includes taxes & fees
7/10 Good! (1,005 reviews)
Staff at front desk was wonderful and helpful. Room had a glass and plastic cup on the floor by bed.
Reviewed on 29 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.
