Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Kingston
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this business-friendly motel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dietz Stadium and Birch Body Care are located nearby.
Hasbrouck House
Save 100% on your flight
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 4-star business-friendly hotel in Stone Ridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.
Urban Cowboy Lodge
Save 100% on your flight
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 5-star luxury lodge in Big Indian. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions Catskill Mountains and Slide Mountain are located nearby.
Kingston Carriage House
Save 100% on your flight
per person
Jul 25 - Jul 30
found 3 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
Stay at this 4-star B&B in Kingston. Enjoy free breakfast, free WiFi, and in-room massages. Popular attractions Hudson River Maritime Museum and Trolley Museum of New York are located nearby.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Save 100% on your flight
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star cottage in Stone Ridge. Enjoy free parking and patios. Popular attractions Mohonk Lake and Tongore Park Beach are located nearby.
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Save 100% on your flight
per person
Jul 17 - Jul 21
just found
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Stay at this 3-star cottage in East Chatham. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Queechy Lake and Shaker Museum and Library are located nearby.
Hampton Inn Schenectady Downtown
per person
Jul 17 - Jul 21
just found
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
Stay at this hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rivers Casino & Resort and Proctors Theater are located nearby.
Pittsfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Pittsfield Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Nov 27 - Thu, Nov 27
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$285 Roundtrip, found 6 days ago
$285
Roundtrip
found 6 days ago
Fri, Nov 21 - Thu, Nov 27
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$336 Roundtrip, found 6 days ago
$336
Roundtrip
found 6 days ago
Tue, Nov 25 - Thu, Nov 27
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$432 Roundtrip, found 6 hours ago
$432
Roundtrip
found 6 hours ago
Tue, Nov 25 - Thu, Nov 27
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$589 Roundtrip, found 6 hours ago
$589
Roundtrip
found 6 hours ago
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