Cheshire Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Ed Gaffny
Top Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
10.45 km from city center
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
The Williams Inn
101 Spring Street, Williamstown, MA
16.77 km from city center
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Hotel Downstreet, Ascend Hotel Collection
40 Main St, North Adams, MA
15.79 km from city center
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
33.29 km from city center
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
21.55 km from city center
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
14.75 km from city center
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
10.84 km from city center
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
18.74 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
18.58 km from city center
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
The Red Lion Inn
30 Main Street, Stockbridge, MA
33.43 km from city center
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
19.61 km from city center
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 ...
The Constance by the Lenox Collection
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
25.02 km from city center
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd, Lenox, MA
19.83 km from city center
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 helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sun, Aug 24 - Sun, Aug 31
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Tue, Aug 26 - Mon, Sep 1
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Tue, Aug 26 - Mon, Sep 1
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Tue, Aug 26 - Mon, Sep 1
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$248 Roundtrip, found 6 days ago
$248
Roundtrip
found 6 days ago
Best points of interest in Cheshire
- St Mary's of the Assumption Church Vacations
- Tanglewood Music Center Vacations
- Jiminy Peak Mountain Resort Vacations
- Williams College Vacations
- National Shrine of the Divine Mercy Vacations
- Green Mountain National Forest Vacations
- Massachusetts Museum of Contemporary Art Vacations
- Mount Greylock Vacations
- The Clark Art Institute Vacations
- Berkshire East Ski Resort Vacations
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