Chatham Vacations

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Top Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
33.49 km from city center
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

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
300 Broadway Albany NY
33.77 km from city center
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 ...
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
32.39 km from city center
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 ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
27.73 km from city center
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

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
27.24 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 ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
26.52 km from city center
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. ...
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
26.9 km from city center
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 ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
31.65 km from city center
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
24.99 km from city center
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 ...
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
99 Miller Rd Castleton-on-Hudson NY
24.95 km from city center
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 ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
27.67 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
34.23 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 ...
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
549 Washington Street Hudson NY
19.92 km from city center
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.
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd Lenox MA
27.34 km from city center
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 ...
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd Hancock MA
32.85 km from city center
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 ...
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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.

Breeze Airways
Thu, Aug 27 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$178 Roundtrip, found 12 hours ago
$178
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Sep 3, priced at $178 found 12 hours ago
American Airlines
Thu, Aug 27 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$251 Roundtrip, found 12 hours ago
$251
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, Aug 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Sep 3, priced at $251 found 12 hours ago
JetBlue Airways
Thu, Aug 27 - Thu, Sep 3
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$257 Roundtrip, found 12 hours ago
$257
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, Aug 27 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Thu, Sep 3, priced at $257 found 12 hours ago
Delta
Sun, Aug 30 - Mon, Aug 31
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$277 Roundtrip, found 12 hours ago
$277
Roundtrip
found 12 hours ago
Select Delta flight, departing Sun, Aug 30 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Aug 31, priced at $277 found 12 hours ago
United
Tue, Sep 1 - Wed, Sep 2
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$287 Roundtrip, found 5 days ago
$287
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 1 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Wed, Sep 2, priced at $287 found 5 days ago