Chatham 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 ...
Country Inn & Suites by Radisson, Downtown Albany New York
300 Broadway Albany NY
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Popular attractions MVP Arena and Palace Theater are ...
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. ...
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 ...
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 ...
Comfort Inn & Suites East Greenbush - Albany
99 Miller Rd Castleton-on-Hudson NY
Book a stay at this business-friendly hotel in Castleton-on-Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
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 ...
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.
Comfort Inn Glenmont - Albany South
37 Route 9W Glenmont NY
Book a stay at this business-friendly hotel in Glenmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
Stay at this hotel in Hancock. Enjoy free parking, 2 hot tubs, and breakfast (surcharge). Our guests praise the property condition 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.
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$142
Roundtrip
found 3 days ago
Tue, Sep 1 - Wed, Sep 2
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$192
Roundtrip
just found
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$212
Roundtrip
found 3 days ago
Tue, Sep 1 - Wed, Sep 2
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217
Roundtrip
just found
Tue, Sep 1 - Wed, Sep 2
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217
Roundtrip
just found
Best points of interest in Chatham
- The Mac-Haydn Theatre Vacations
- Tanglewood Music Center Vacations
- Jiminy Peak Mountain Resort Vacations
- National Shrine of the Divine Mercy Vacations
- Hudson River Vacations
- Norman Rockwell Museum Vacations
- Lee Premium Outlets Vacations
- Olana State Historic Site Vacations
- Taconic State Park Vacations
- Ski Butternut Vacations
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