Chester Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (2,238 reviews)
Staff was super helpful and hospitable! Shout out to Jim! We were here during a blizzard and they actually cleaned the snow off of our car! Room was lovely and clean. Great breakfast.
Reviewed on 24 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.960.077 ₫ per night from 8 Mar to 9 Mar
2.960.077 ₫
3.886.553 ₫ total
8 Mar - 9 Mar
includes taxes & fees
9/10 Wonderful! (862 reviews)
👍
Reviewed on 23 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.406.028 ₫ per night from 4 Mar to 5 Mar
2.406.028 ₫
2.687.534 ₫ total
4 Mar - 5 Mar
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
Yrs
Reviewed on 23 Feb 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.
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.
