Sheffield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
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 ...
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 ...
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. ...
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 ...
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 ...
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
Stay at this motel in Lenox. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
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 ...
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. ...
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 ...
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 ...
Little Cat Lodge
37 Catamount Rd Copake Falls NY
Stay at this hotel in Copake Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Catamount Ski Area and Catamount Aerial Adventure ...
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 ...
The Little Lion
506 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
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.
Fri, Sep 11 - Sun, Sep 13
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217
Roundtrip
found 5 days ago
Sun, Sep 13 - Mon, Sep 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$237
Roundtrip
found 5 days ago
Thu, Sep 10 - Mon, Sep 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$277
Roundtrip
found 1 day ago
Thu, Sep 10 - Mon, Sep 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$307
Roundtrip
found 1 day ago
Tue, Sep 22 - Wed, Sep 23
TPA
Tampa Intl.
ALB
Albany Intl.
$311
Roundtrip
found 1 hour ago
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