Chester Travel Guide
Tourist Guide
Visit Chester
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (573 reviews)
I’d stay there again
"Everything was nice expect the “last guests” socks we found tangled in the pull out sofa bed."
Reviewed on 17 Aug. 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
The price is AU$199 per night from 2 Sept to 3 Sept
AU$199
2 Sept - 3 Sept
includes taxes & fees
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,278 reviews)
"Na"
Reviewed on 18 Aug. 2025
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
The price is AU$185 per night from 24 Aug to 25 Aug
AU$185
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,226 reviews)
"I enjoyed my stay"
Reviewed on 18 Aug. 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.
The Ponds at Foxhollow
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (125 reviews)
"The unit was in very good shape and in an excellent location but we had been promised an indoor pool but it was under renovation. It would be nice if we were told that in advance. Most of the front desk people were very nice but one person doesn’t seem to like customers. Overall a good ..."
Reviewed on 14 Aug. 2025
Peace and quiet on the lake
Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (216 reviews)
Lake House Getaway with Access to Berkshire Highlights
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any ..."
Reviewed on 31 Jul. 2025
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Becket
Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (187 reviews)
"Great. It was peaceful and relaxing. Had everything you needed. Very nice place in a beautiful location. Wonderful screen porch. We loved everything about it."
Reviewed on 16 Aug. 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.