Cheshire, MA
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$122 nightly
The price is $136 total per night from Sep 24 to Sep 25
$136 total
Sep 24 - Sep 25
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! (2,668 reviews)
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Reviewed on Sep 22, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$109 nightly
The price is $121 total per night from Oct 1 to Oct 2
$121 total
Oct 1 - Oct 2
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! (1,151 reviews)
"Clean room comfortABLE"
Reviewed on Sep 22, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
$117 nightly
The price is $131 total per night from Sep 28 to Sep 29
$131 total
Sep 28 - Sep 29
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 ...
9.2/10 Wonderful! (1,004 reviews)
"The room was spacious, clean and comfortable. I will definitely stay there again."
Reviewed on Sep 21, 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! (2,668 reviews)
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"
Reviewed on Sep 22, 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! (1,151 reviews)
"Clean room comfortABLE"
Reviewed on Sep 22, 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! (149 reviews)
"Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely."
Reviewed on Sep 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.
Stay near popular Cheshire attractions
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- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- Green Mountain National Forest
- Williams College
- Massachusetts Museum of Contemporary Art
- Norman Rockwell Museum
- National Shrine of the Divine Mercy
- Mount Greylock
- Berkshire East Ski Resort
- Lee Premium Outlets
- Bousquet Ski Area
- Hancock Shaker Village
- The Mount
- The Clark Art Institute
- Jacob's Pillow
- Mount Greylock State Reservation Visitor Center
- Shakespeare and Company
- Southern Vermont College
- Bridge of Flowers
- Natural Bridge State Park
- Naumkeag Museum
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Wyndhurst Golf & Club
- Ventfort Hall Mansion and Gilded Age Museum
- Taconic Golf Club
- Sterling and Francine Clark Art Institute
- Berkshire Museum
- Grafton Lakes State Park
- Williamstown Theatre Festival
- Lenox Library
