Cheshire Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
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 ...
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 ...
The Yankee Inn
461 Pittsfield Rd Lenox MA
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 ...
Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
Book a stay at this ski hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. ...
Berkshires Untold
194 Pittsfield Rd Lenox MA
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Red Lion Inn
30 Main Street Stockbridge MA
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Hotel On North
297 North Street Pittsfield MA
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms ...
The Williams Inn
101 Spring Street Williamstown MA
Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Book a stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
The Whitlock
16 Church St Lenox MA
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
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 ...
The Cornell Inn, Lenox & The Berkshires
203 Main St Lenox MA
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular ...
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
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.
Tue, Oct 27 - Tue, Nov 17
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$287
Roundtrip
found 5 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$307
Roundtrip
found 5 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$307
Roundtrip
found 5 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$307
Roundtrip
found 5 days ago
Thu, Oct 29 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$307
Roundtrip
found 5 days ago
Best points of interest in Cheshire
- St Mary's of the Assumption Church Vacations
- Jiminy Peak Mountain Resort Vacations
- Tanglewood Music Center Vacations
- Green Mountain National Forest Vacations
- Williams College Vacations
- Norman Rockwell Museum Vacations
- Massachusetts Museum of Contemporary Art Vacations
- National Shrine of the Divine Mercy Vacations
- Mount Greylock Vacations
- Berkshire East Ski Resort Vacations
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