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
$108 nightly
The price is $120 total per night from Oct 22 to Oct 23
$120 total
Oct 22 - Oct 23
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
Explore a world of travel with Expedia
- Budget in Pittsfield
- Hotels in Cheshire
- Privatevacationhomes in Pittsfield
- Preferred Hotels in Cheshire
- Hotels in Dalton
- Hotels in Hancock
- 3 Star Hotels in North Adams
- Hotels in Adams
- Best Western Hotels in Williamstown
- Bedandbreakfast in Adams
- Motels in Adams
- Hotels in Lanesborough
- Hotels in Pittsfield
- Tennis in Hancock
- 4 Star Hotels in Ashuwillticook Rail Trail
- Inns in Dalton
- Resorts in Pittsfield
- Cabins in Cheshire
- Flights to Cheshire
- Oceanic Airlines Nantucket (ACK) to Pittsfield (PSF) flights
- Flights to Pittsfield
- Flights to Adams
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights to Dalton
- Flights to Williamstown
- Oceanic Airlines Lexington (LEX) to Pittsfield (PSF) flights
- Flights to North Adams
- Flights from Mississauga (YYZ) to Pittsfield (PSF)
- Western Massachusetts All Inclusive Vacation Packages
- Where to stay in Northampton
- Mount Greylock
- Where to stay in Lenox
- Where to stay in The Berkshires
- Visit Lanesborough
- Visit Stockbridge
- Cheshire Vacations
- Western Massachusetts All Inclusive Vacation Packages
- Visit Hancock
- Visit Pittsfield
- Western Massachusetts All Inclusive Vacation Packages
- Jiminy Peak Mountain Resort
- Visit North Adams
- Lenox Vacations
- Visit Lenox
- Visit Charlemont
- Visit Williamstown
- Western Massachusetts All Inclusive Vacation Packages
- Western Massachusetts All Inclusive Vacation Packages
- Visit Shelburne Falls
- Where to stay in Great Barrington
- Where to stay in Greenfield
- The Clark Art Institute
- Where to stay in Ashuwillticook Rail Trail
- The Berkshires All Inclusive Vacation Packages
- Western Massachusetts All Inclusive Vacation Packages
- Where to stay in Pittsfield
- Visit Lee
- Western Massachusetts All Inclusive Vacation Packages
- Visit Becket
- Visit Adams
- Where to stay in Stockbridge
- Where to stay in Hadley
- The Berkshires All Inclusive Vacation Packages
- Visit South Lee
- Stockbridge Vacations
- Drury Vacations
- Where to stay in Mohawk Trail State Forest
- Hancock Vacations
- Visit Dalton
- Visit Otis
- Adams Vacations
- Western Massachusetts All Inclusive Vacation Packages
- The Berkshires All Inclusive Vacation Packages
- Tanglewood Music Center
- Where to stay in Shelburne Falls
- Visit Great Barrington
- Pickup Car Rentals in North Adams
- Hertz Rental Cars in Pittsfield
- Car rentals in Williamstown
- Car rentals in Pittsfield
- Van Car Rentals in Pittsfield
- Car rentals in Hancock
- Car rentals in Adams
- Luxury Car Rentals in Pittsfield
- Car rentals in North Adams
- Enterprise Rental Cars in Pittsfield
- Car rentals in Cheshire
- 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
- The Mount
- Hancock Shaker Village
- Jacob's Pillow
- Mount Greylock State Reservation Visitor Center
- The Clark Art Institute
- Bridge of Flowers
- Natural Bridge State Park
- Shakespeare and Company
- Southern Vermont College
- Naumkeag Museum
- Berkshire Museum
- Wyndhurst Golf & Club
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Ventfort Hall Mansion and Gilded Age Museum
- Taconic Golf Club
- Sterling and Francine Clark Art Institute
- Lenox Library
- Grafton Lakes State Park
