Chester
Travel Guide
Visit Chester
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is €125 per night from 6 Jul to 7 Jul
€125
6 Jul - 7 Jul
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,002 reviews)
"Friendly, helpful, high-morale staff. Decent location, minutes from Historic Lenox. The room was excellent. Very good breakfast. We plan to stay at the Yankee again."
Reviewed on 27 Jun 2026
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
The price is €83 per night from 19 Jul to 20 Jul
€83
19 Jul - 20 Jul
includes taxes & fees
Stay at this golf hotel in West Springfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
7/10 Good! (1,004 reviews)
"The breakfast was very good and the place for the price was ok, I stayed for two nights on the third floor; the place is currently being renovated. The room was clean, but the hallway -despite being a non-smoking area- smelled like cigarettes on the first day, but smelled much, much better by the ..."
Reviewed on 27 Jun 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundable
The price is €157 per night from 27 Jul to 28 Jul
€157
27 Jul - 28 Jul
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (1,003 reviews)
"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. ..."
Reviewed on 26 Jun 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 Wi-Fi, free parking and a fitness centre. 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 9 Feb 2026
Cozy Riverside Berkshires Retreat
Great Barrington MA
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions National Shrine of the Divine Mercy and ...
9.4/10 Exceptional! (16 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
Reviewed on 13 Jun 2026
Private Island - Largest Fresh Water Reservoir in Mass
Otis MA
Stay at this cottage in Otis. Enjoy free Wi-Fi, a fitness centre 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 14 Oct 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.
