Hillsdale Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Top Hotel Deals
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 ...
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 ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
282 Cairo Junction Rd Catskill NY
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
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 ...
Pocketbook Hotel and Bath
549 Washington Street Hudson NY
Stay at this hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Oakdale Beach and Stoddard Corner are located nearby.
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. ...
Howard Johnson by Wyndham Saugerties
2764 Route 32 Saugerties NY
Book a stay at this business-friendly hotel in Saugerties. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular ...
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 ...
St. Charles Hotel
16 Park Place Hudson NY
Stay at this hotel in Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
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 ...
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 ...
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, Sep 29 - Tue, Oct 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$287
Roundtrip
found 15 hours ago
Fri, Sep 25 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$327
Roundtrip
found 15 hours ago
Sat, Sep 26 - Fri, Oct 9
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$337
Roundtrip
found 15 hours ago
Sat, Sep 26 - Fri, Oct 9
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$391
Roundtrip
found 15 hours ago
Tue, Sep 15 - Tue, Sep 22
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$445
Roundtrip
found 6 days ago
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