Chester
Travel Guide
Visit Chester
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is CA $181 per night from Jul 6 to Jul 7
CA $181
CA $202 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,002 reviews)
"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical ..."
Reviewed on Jul 2, 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
The price is CA $135 per night from Aug 2 to Aug 3
CA $135
CA $155 total
Aug 2 - Aug 3
includes taxes & 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! (1,004 reviews)
"The staff is terrible"
Reviewed on Jul 4, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is CA $190 per night from Aug 4 to Aug 5
CA $190
CA $244 total
Aug 4 - Aug 5
includes taxes & 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! (1,015 reviews)
"Room was clean. Beds were old and uncomfortable. Place is very dated. Toilet seat was broken off. We needed a clean, inexpensive place to stay for a night, but I would’ve been disappointed if we had to stay there longer."
Reviewed on Jul 4, 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
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 National Shrine of the Divine Mercy and ...
9.4/10 Exceptional! (18 reviews)
"We thoroughly enjoyed our stay. The house was very comfortable and convenient. We loved Studley, the resident cat - such a sweetheart."
Reviewed on Jun 29, 2026
Private Island - Largest Fresh Water Reservoir in Mass
Otis MA
Stay at this cottage in Otis. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Larkum Pond and Otis Reservoir are located nearby.
8.6/10 Excellent! (9 reviews)
"Location was wonderful, panoramic lake view.Glassed in porch was the primo spot to just relax and chill. Main bedroom and living room were good size. Kitchen was well appointed except for one staple item, no microwave! Second bedroom and bathroom are very small. You’ll want to bring your own linens, ..."
Reviewed on Oct 14, 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.
