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.
The Yankee Inn
Price was CA $1,202, price is now CA $1,005 per person
CA $1,005
per person
Jun 13 - Jun 20
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
My partner and I just moved back to MA so we are local to the area. We have stayed there just to have an evening of respite together and solo and send our family there during holidaze! Very friendly staff, comfortable rooms, prime location, and breezy breakfast options.
Reviewed on May 8, 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 $162 per night from May 25 to May 26
CA $162
CA $176 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Room was clean and comfortable and quiet. There was plenty of parking. Rooms were recently remodeled. There wasn't a lot to choose from for breakfast but it was adequate. The landline in our room didn't work so if you wanted the front desk, you had to walk there. (We asked but no one came to fix ...
Reviewed on May 11, 2026
Hampton Inn Bennington
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from May 17 to May 18
CA $225
CA $246 total
May 17 - May 18
includes taxes & fees
8.6/10 Excellent! (1,002 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 $189 per night from May 14 to May 15
CA $189
CA $206 total
May 14 - May 15
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.
