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 includes 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! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."
Reviewed on Aug 11, 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
$93 nightly
The price is $106 total per night from Aug 27 to Aug 28
$106 total
Aug 27 - Aug 28
Total includes taxes and fees
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,006 reviews)
Enjoyable one night stay at the Quality Inn!
"I recently stayed 1 night at the Quality Inn while in the area for Six Flags. This is my go to hotel when visiting the park as it is a great value and about 15 minutes away. I checked in later, around 9pm, and long time employee Rick was at the desk. He is never shy about his dislike for computers ..."
Reviewed on Aug 12, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
$116 nightly
The price is $132 total per night from Sep 2 to Sep 3
$132 total
Sep 2 - Sep 3
Total includes 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! (1,268 reviews)
"Everyone was nice. It needs a little updating/painting"
Reviewed on Aug 12, 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! (124 reviews)
"Staff was responsive and very helpful. The property was well-landscaped and clean. Check-in and out were easy. The outdoor pool area was very nice, however, the unheated pool was too cold. The property was close to Lenox, Lee, and Stockbridge, all offering lots of dining options. The apartment was ..."
Reviewed on Jul 28, 2025
The Clearing - Quiet - Close To Nature
Cummington
Stay at this cottage in Cummington. Enjoy free WiFi, private pools, and a garden. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (187 reviews)
My stay
"Everything was great: kitchen, WiFI, etc."
Reviewed on Aug 6, 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
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