Search Deals onBennington Vacation Packages
Bennington Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Aspen At Manchester
Price was $600, price is now $440 per person
$440
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.
Absolutely loved this property! Amazing location, super clean and spacious rooms! We loved being in close proximity to the town, which was soooooo amazingly pet friendly! We will definitely be back
Reviewed on Sep 14, 2026
The Cornell Inn, Lenox & The Berkshires
Price was $1,408, price is now $984 per person
$984
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Tanglewood Music Center and Lenox Library are located nearby.
Prospect Berkshires
Price was $2,724, price is now $1,933 per person
$1,933
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) 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 Perch Hotel
Price was $1,599, price is now $1,161 per person
$1,161
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.
Holiday Inn Club Vacations Oak 'n Spruce Resort
Price was $811, price is now $593 per person
$593
per person
Oct 22 - Oct 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Book a stay at this ski hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
The Ponds at Foxhollow
Price was $1,036, price is now $768 per person
$768
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located nearby.
Our unit was very comfortable for 2 senior couples. We were only there for the weekend so we didn’t use any of the amenities but, the property is lovely.
Reviewed on Sep 4, 2026
The White House Inn
Price was $581, price is now $465 per person
$465
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions South Main Street and Pettee Memorial Library are located nearby.
South Shire
Price was $563, price is now $459 per person
$459
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
Stay at this B&B in Bennington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Bennington Arts Guild Gallery and Fiddlehead at Four Corners are located nearby.
Romantic old Victorian with charming decor. Nice walkable distance to downtown.
Reviewed on Sep 15, 2026
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.
Thu, Oct 29 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$151 Roundtrip, found 1 day ago
$151
Roundtrip
found 1 day ago
Tue, Nov 3 - Sat, Nov 14
LAX
Los Angeles Intl.
ALB
Albany Intl.
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Sat, Sep 26 - Tue, Sep 29
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$264 Roundtrip, found 12 hours ago
$264
Roundtrip
found 12 hours ago
Thu, Dec 3 - Thu, Dec 10
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
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