Chester Travel Guide
Tourist 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! (2,232 reviews)
We were greeted immediately and felt welcomed as we walked in! The gentleman at the front desk was very kind and welcoming! Whirlpool and indoor pool were wonderful and you can’t beat the location!
Reviewed on 20 Feb 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is NZ$250 per night from 23 Feb to 24 Feb
NZ$250
23 Feb - 24 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! (850 reviews)
Room was clean and suite was huge, staff was friendly and helpful, pool and game room were great for my kids. All was great for a Feb vacation getaway!
Reviewed on 20 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
The price is NZ$173 per night from 2 Mar to 3 Mar
NZ$173
2 Mar - 3 Mar
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. ...
9.2/10 Wonderful! (1,008 reviews)
Beautiful room with a fireplace.
Reviewed on 19 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 ...
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...
Reviewed on 9 Feb 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 ...
10/10 Exceptional! (19 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
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough MA
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
10/10 Exceptional! (10 reviews)
Perfect spot to get in a few days of skiing at Jiminy. Well stocked with the basics and hot tub was great. Very responsive host.
Reviewed on 18 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.
