Chester
Travel Guide
Visit Chester
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is CA $107 per night from Sep 7 to Sep 8
CA $107
CA $150 total
Sep 7 - Sep 8
includes taxes & fees
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! (583 reviews)
Satisfied customer
"as good as the last time we stayed there."
Reviewed on Aug. 21, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
The price is CA $156 per night from Sep 1 to Sep 2
CA $156
CA $177 total
Sep 1 - Sep 2
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! (1,270 reviews)
"The doors are paper thin so you hear everything in the corridor. Our tv did not work during our stay but the hotel was kind to discount us at checkout. There is no housekeeping service during the stay. It’s a nice property but the things above took away from the experience unfortunately."
Reviewed on Aug. 21, 2025
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
The price is CA $144 per night from Aug 24 to Aug 25
CA $144
CA $167 total
Aug 24 - Aug 25
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! (2,229 reviews)
"Great place and friendly staff."
Reviewed on Aug. 21, 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 ...
8.4/10 Very Good! (126 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 Aug. 14, 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 Jul. 31, 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 Aug. 16, 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 during your trip to Chester. Wander the lakeside and forest in this relaxing area.