Search Deals onPittsfield Vacation Packages
Pittsfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Club Wyndham Bentley Brook
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Prospect Berkshires
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area are located nearby.
The Equinox Golf Resort & Spa
Save 100% on your flight
per person
Oct 20 - Oct 26
found 12 hours ago
Roundtrip non-stop flight included
Sarasota (SRQ) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pocketbook Hotel and Bath
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Book a stay at this spa hotel in Hudson. Enjoy free WiFi, a full-service spa, and a 24-hour front desk. Popular attractions Hudson Area Library and Stoddard Corner are located nearby.
The Old Catskill Game Farm Inn
Save 100% on your flight
per person
Oct 4 - Oct 8
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star historic guesthouse in Catskill. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Kaaterskill Falls and North-South Lake Campground & Day Use Area are located nearby.
The Wiltwyck
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Stay at this 3.5-star guesthouse in Kingston. Enjoy free WiFi, free parking, and Netflix. Popular attractions Senate House State Historic Site and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Save 100% on your flight
per person
Oct 4 - Oct 8
found 13 hours ago
Roundtrip flight included
Tampa (TPA) 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.
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.
Tue, Nov 4 - Tue, Nov 4
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Fri, Nov 7 - Sun, Nov 9
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$333 Roundtrip, found 2 days ago
$333
Roundtrip
found 2 days ago
Fri, Nov 7 - Sun, Nov 9
RSW
Southwest Florida Intl.
ALB
Albany Intl.
$349 Roundtrip, found 2 days ago
$349
Roundtrip
found 2 days ago
Fri, Oct 10 - Sun, Oct 12
JFK
John F. Kennedy Intl.
ALB
Albany Intl.
$440 Roundtrip, found 2 days ago
$440
Roundtrip
found 2 days ago
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