Cheshire, MA
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$128 nightly
The price is $143 total per night from Aug 31 to Sep 1
$143 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,514 reviews)
"The 1 bedroom suite was comfortable and had everything we needed. The one thing that could be improved would be the mattress on the pull out couch. Needs to be thicker and less bumpy."
Reviewed on Aug 8, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
$137 nightly
The price is $153 total per night from Aug 9 to Aug 10
$153 total
Aug 9 - Aug 10
Total with taxes and 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 ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$140 nightly
The price is $154 total per night from Aug 31 to Sep 1
$154 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,054 reviews)
"Some rooms could use “freshening”"
Reviewed on Aug 8, 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.
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,514 reviews)
"The 1 bedroom suite was comfortable and had everything we needed. The one thing that could be improved would be the mattress on the pull out couch. Needs to be thicker and less bumpy."
Reviewed on Aug 8, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,054 reviews)
"Some rooms could use “freshening”"
Reviewed on Aug 8, 2026
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 The Mount are located ...
8.6/10 Excellent! (145 reviews)
"Quiet property. Convenient location."
Reviewed on Aug 2, 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.
Stay near popular Cheshire attractions
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- Castles in Lanesborough
- Visit Lee
- Visit Becket
- Visit Savoy
- East Hoosac Quaker Meetinghouse
- Visit Ashfield
- Visit Hancock
- Visit Cummington
- Visit Shelburne Falls
- Visit Buckland
- Visit Williamstown
- Visit Charlemont
- Visit Lanesborough
- Jiminy Peak Mountain Resort
- Mount Greylock
- Visit Middlefield
- Visit Great Barrington
- Visit New Ashford
- Adams Vacations
- Visit Berkshire County
- Visit South Lee
- Visit Dalton
- Visit Drury
- Where to stay in Ashuwillticook Rail Trail
- Visit West Stockbridge
- Visit Hawley
- Visit Pittsfield
- Cheshire Vacations
- Visit Stockbridge
- Visit Hinsdale
- Mount Greylock State Reservation Visitor Center
- Visit Adams
- Visit Chesterfield
- Visit Worthington
- Visit North Adams
- Visit Rowe
- Visit Lenox
- Visit Richmond
- Susan B. Anthony Birthplace Museum
- Wahconah Falls State Park
- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- Green Mountain National Forest
- Massachusetts Museum of Contemporary Art
- Williams College
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
- Lee Premium Outlets
- Mount Greylock
- Berkshire East Ski Resort
- Jacob's Pillow
- The Clark Art Institute
- The Mount
- Hancock Shaker Village
- Mount Greylock State Reservation Visitor Center
- Bousquet Ski Area
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Lenox Library
- Sterling and Francine Clark Art Institute
- Bridge of Flowers
- Berkshire Botanical Garden
- Naumkeag Museum
- Harriman Reservoir
- Grafton Lakes State Park
- Williamstown Theatre Festival
- Colonial Theater
- Wyndhurst Golf & Club
- Natural Bridge State Park
- Berkshire Mountain Country Store
