Search Deals onBennington Vacation Packages
Bennington Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
The Ponds at Foxhollow
Save 100% on your flight
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
Gedney Farm
Save 100% on your flight
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library are located nearby.
Berkshire Mountain Lodge
Save 100% on your flight
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Lodges At Cresthaven
Save 100% on your flight
per person
Jul 18 - Jul 20
found 24 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
Stay at this 4-star beach lodge in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Fort William Henry and Hearthstone Point Campground are located nearby.
Life House Berkshires
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Save 100% on your flight
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this 3-star cottage in Lee. Enjoy patios, in-room washers/dryers, and in-room fireplaces. Popular attractions Tanglewood Music Center and Greenock Country Club are located nearby.
Wilder House Berkshires
per person
Jul 7 - Jul 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.
Bennington Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Bennington 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.
Wed, May 14 - Sun, May 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$187 Roundtrip, found 4 days ago
$187
Roundtrip
found 4 days ago
Fri, Jun 6 - Wed, Jun 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$221 Roundtrip, found 18 hours ago
$221
Roundtrip
found 18 hours ago
Wed, Jul 2 - Wed, Jul 9
TPA
Tampa Intl.
ALB
Albany Intl.
$235 Roundtrip, found 14 hours ago
$235
Roundtrip
found 14 hours ago
Mon, Jul 28 - Tue, Aug 5
SFO
San Francisco Intl.
ALB
Albany Intl.
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days ago
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