Chester, MA
Travel Guide
Visit Chester
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$111 nightly
The price is $124 total per night from May 28 to May 29
$124 total
May 28 - May 29
Total with taxes and fees
Book a stay at this 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! (927 reviews)
Room very spacious and clean. Full kitchen is a great bonus.
Reviewed on May 4, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
$101 nightly
The price is $113 total per night from May 12 to May 13
$113 total
May 12 - May 13
Total with taxes and fees
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (934 reviews)
Great room, quaint hotel. Nice bar, lounge area. Great staff, very helpful
Reviewed on May 10, 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
$85 nightly
The price is $97 total per night from May 31 to Jun 1
$97 total
May 31 - Jun 1
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! (1,008 reviews)
Very convenient location.
Reviewed on May 9, 2026
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 aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and National Shrine of the ...
8.6/10 Excellent! (141 reviews)
I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...
Reviewed on Feb 9, 2026
Peace and quiet on the lake
Becket MA
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! (236 reviews)
Great spot on the water!
Reviewed on Apr 23, 2026
Cozy Riverside Berkshires Retreat
Great Barrington MA
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Monument Mountain Reservation and Art ...
9.2/10 Wonderful! (14 reviews)
Awesome location. Host was very informative and responsive.
Reviewed on Apr 15, 2026
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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- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Mount Holyoke College
- Big E
- Norman Rockwell Museum
- Smith College
- Holyoke Mall
- Eastern States Exposition
- The Mount
- Jacob's Pillow
- Lee Premium Outlets
- Ski Butternut
- Historic Northampton
- Naumkeag Museum
- Berkshire Botanical Garden
- Connecticut River
- Bousquet Ski Area
- Goose Pond Reservation
- Otis Reservoir
- Chicopee Falls Dam
- Berkshire Museum
- Smith College Botanic Garden
- Shakespeare and Company
- Wyndhurst Golf & Club
- Olympia Ice Center
- Don Muller Gallery