Chester, MA
Travel Guide
Visit Chester
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and 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! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
Reviewed on Aug 23, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
$112 nightly
The price is $127 total per night from Sep 1 to Sep 2
$127 total
Sep 1 - Sep 2
Total with taxes and 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! (1,272 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
$150 nightly
The price is $168 total per night from Sep 1 to Sep 2
$168 total
Sep 1 - Sep 2
Total with taxes and 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! (2,217 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! (188 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.
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- Big E
- Tanglewood Music Center
- Eastern States Exposition
- Smith College
- National Shrine of the Divine Mercy
- Mount Holyoke College
- Norman Rockwell Museum
- Ski Butternut
- Connecticut River
- Holyoke Mall
- Lee Premium Outlets
- Jacob's Pillow
- The Mount
- Bousquet Ski Area
- Naumkeag Museum
- Olympia Ice Center
- Ventfort Hall Mansion and Gilded Age Museum
- Berkshire Botanical Garden
- Historic Northampton
- Berkshire Museum
- Otis Reservoir
- Shakespeare and Company
- Berkshire Mountain Country Store
- Smith College Botanic Garden
- Goose Pond Reservation
- Colonial Theater