Chester
Travel Guide
Visit Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants and room service. Our guests praise the breakfast and the pool in their reviews. Popular ...
9.2/10 Wonderful! (2,245 reviews)
Staff was very nice, room was clean. Breakfast was good.
Reviewed on 9 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is €126 per night from 16 Feb to 17 Feb
€126
16 Feb - 17 Feb
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (831 reviews)
The doors wouldn’t stay locked
Reviewed on 6 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
The price is €87 per night from 22 Feb to 23 Feb
€87
22 Feb - 23 Feb
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9/10 Wonderful! (1,014 reviews)
All of the above plus its consistency. Reliable stay every time.
Reviewed on 11 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.
The Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.4/10 Very Good! (140 reviews)
Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned.
Reviewed on 3 Jan 2026
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge MA
Stay at this family-friendly holiday home in West Stockbridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Stockbridge Bowl and Berkshire ...
9.8/10 Exceptional! (134 reviews)
We always love visiting this house! It is comfortable, clean, and very welcoming. Highly recommend!
Reviewed on 25 Jan 2026
The Kemble- Built by a US Secretary of State in Lenox
Lenox MA
Stay at this family-friendly villa in Lenox. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Ventfort Hall Mansion and Gilded Age ...
9.8/10 Exceptional! (18 reviews)
We stayed at The Kemble, the historic Lenox estate built by a U.S. Secretary of State, for a large family reunion with 10 adults and 16 children—and it was, without question, the best large-house experience we’ve ever had.We rent a large home every year, and nothing has come close to this. The house ...
Reviewed on 13 Jan 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.
