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
The price is 3.237.226 ₫ per night from 15 Apr to 16 Apr
3.237.226 ₫
3.760.851 ₫ total
15 Apr - 16 Apr
includes taxes & fees
9.4/10 Exceptional! (2,256 reviews)
Clean room and comfortable bed.
Reviewed on 14 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.166.136 ₫ per night from 19 Apr to 20 Apr
2.166.136 ₫
3.008.010 ₫ total
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (905 reviews)
Very friendly staff. The hotel and property was very clean and well maintained the outside. The outside Jacuzzi was amazing. The pool was great very nice hotel all the way around.
Reviewed on 12 Apr 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.067.163 ₫ per night from 21 Apr to 22 Apr
2.067.163 ₫
2.309.020 ₫ total
21 Apr - 22 Apr
includes taxes & fees
9/10 Wonderful! (895 reviews)
We did not see a pool
Reviewed on 8 Apr 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.
