Bennington Vacation Packages
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Your Bennington Vacation
Our vacation packages to Bennington allow you to create your own adventure. Tailor your getaway to your interests and needs and make every moment count in this interesting city. Every trip to Bennington needs a well-planned itinerary. Fill yours with famous sights like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Don't put off visiting this city any longer. The ultimate Bennington vacation is only a few clicks away with Expedia.
Top Bennington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,315, price is now CA $1,074 per person
CA $1,074
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,010 reviews)
Staff was great. Bathrooms could use a little upkeep.
Reviewed on May 1, 2026
The Cornell Inn, Lenox & The Berkshires
Price was CA $2,976, price is now CA $2,089 per person
CA $2,089
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
Lovely Inn , comfy bed and suite. The breakfast was delicious…especially enjoyed the frittata, fresh baked sweet breads, and latte. Appreciated the fireplace and cognac nightcap served on on a cool April evening ,coming back from a delicious dinner in Lenox. Kool speak easy style bar, good vibes!
Reviewed on May 1, 2026
Hideaway Inn Lenox
Price was CA $2,103, price is now CA $1,612 per person
CA $1,612
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6/10 (1 review)
The room was comfortable and well done. There was no heat in our room with no control for the air unit. There was also a drip coming from the exhaust fan in the bathroom. We were only there one night so I didn't call for support.
Reviewed on Apr 16, 2026
The White House Inn
Price was CA $1,881, price is now CA $1,550 per person
CA $1,550
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (309 reviews)
This property was a delight. Complementary breakfast was terrific along with the restaurant for dinner. Rooms were clean and quiet.
Reviewed on Apr 28, 2026
Vacation Village in the Berkshires
Price was CA $1,337, price is now CA $1,105 per person
CA $1,105
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,342 reviews)
Muito bom para aproveitar em família ou a 2
Reviewed on May 3, 2026
Bennington Hotel Deals
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from May 26 to May 27
CA $161
CA $176 total
May 26 - May 27
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
nice hotel. good bed. tv didn't work. staff tried to fix. when we checked out we asked to be comped a room the next time we were in town. we were told yes, the mgr would call us. never heard from them.
Reviewed on May 6, 2026
Hampton Inn Bennington
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jun 7 to Jun 8
CA $223
CA $243 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Loves the grab and go bagels in the morning.
Reviewed on Apr 29, 2026
Knotty Pine
130 Northside Dr Bennington VT
The price is CA $172 per night from May 13 to May 14
CA $172
CA $188 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (98 reviews)
Room was very clean very easy access to the room
Reviewed on May 4, 2026
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.
What to do in Bennington
Vermont RT 100 App-Guided Driving Audio Tour
CA $23
per traveller
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
