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.
Schuyler Yacht Basin
Price was CA $1,381, price is now CA $1,224 per person
CA $1,224
per person
Jun 4 - Jun 8
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.6/10 Excellent! (20 reviews)
What a beautiful place it was for an escape weekend! Definitely would recommend this beautiful place!
Reviewed on Oct 6, 2025
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
Price was CA $1,435, price is now CA $1,282 per person
CA $1,282
per person
Jun 4 - Jun 8
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.8/10 Excellent! (1,061 reviews)
We got a phone stuck between the bed frame and the wall and they told us there was nothing they could do. I asked for a late check out so we could figure it out on our own and they said no….
Reviewed on Apr 14, 2026
Homewood Suites By Hilton Schenectady
East Glenville
Price was CA $1,462, price is now CA $1,340 per person
CA $1,340
per person
Jun 4 - Jun 8
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The staff texted daily to ask if we needed anything. The kitchenette was well appointed and the room was spacious. The bath was spacious and clean as well. The pool was clean and our daughter was thrilled with the view of the trains passing through several times per day. The room was quiet and the grounds were lovely.
Reviewed on Apr 17, 2026
Bennington Hotel Deals
Hampton Inn Bennington
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Apr 26 to Apr 27
CA $200
CA $218 total
Apr 26 - Apr 27
includes taxes & fees
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 4 to May 5
CA $173
CA $189 total
May 4 - May 5
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Needed a place to stay last minute. Easily booked through hotels.com. Was able to check in early, staff super nice and helpful. Very clean, comfy bed. My only gripe is they are hard to find - their sign should say to enter from Harrison ave.
Reviewed on Apr 14, 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Apr 22 to Apr 23
CA $230
CA $251 total
Apr 22 - Apr 23
includes taxes & fees
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.
