Chester, MA
Travel Guide
Visit Chester
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Nov 4 to Nov 5
$126 total
Nov 4 - Nov 5
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 ...
9/10 Wonderful! (744 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you
Reviewed on Nov 2, 2025
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
$114 nightly
The price is $129 total per night from Nov 10 to Nov 11
$129 total
Nov 10 - Nov 11
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! (1,296 reviews)
I Have stayed here numerous times and I am never disappointed.Clean room good location good breakfast
Reviewed on Oct 31, 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
$86 nightly
The price is $99 total per night from Dec 2 to Dec 3
$99 total
Dec 2 - Dec 3
Total with 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! (1,035 reviews)
Breakfast was a little cold and had clearly sat prior to the opening of breakfast
Reviewed on Oct 26, 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! (132 reviews)
All as promised!
Reviewed on Oct 21, 2025
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Great Barrington, MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Monument Mountain Reservation ...
9/10 Wonderful! (2 reviews)
Great location with nice space to hangout as a group - appreciated the music and games options. Comfortable space. Host was very responsive and checked in with us. Small bathroom for 4 people but nice big windows throughout the house for good light and great views. Everything was clean and ready ...
Reviewed on Oct 27, 2025
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Lee
Stay at this vacation home in Lee. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and Greenock Country Club are ...
9.4/10 Exceptional! (15 reviews)
The house was very clean and the kitchen was well stocked. All you need to do is add food. I did have a few questions and the managers response was extremely quick. We walked to town for dining, shopping and a little further was a great hike. Lee is close to many other fun towns too, so easy access ...
Reviewed on Oct 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.
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