Old Bennington Vacation Packages
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Your Old Bennington Vacation
The rich history and spectacular views are just the start of the things Old Bennington has on offer. Experience the very best of this interesting city the way you want with a personalized Old Bennington vacation package. If your trip to Old Bennington includes a little sightseeing, check out famous attractions like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Expedia will help you escape the everyday. Tailor your vacation to Old Bennington to suit your travel style, whatever that may look like.
Top Old Bennington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Wilburton Inn
Price was CA $4,585, price is now CA $3,590 per person
CA $3,590
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Albany (ALB)
9/10 Wonderful! (130 reviews)
This is a magical place. We enjoyed a very relaxing four days at the Wilburton. First time, we will be back!
Reviewed on Mar 21, 2026
The Red Lion Inn
Price was CA $3,271, price is now CA $2,609 per person
CA $2,609
per person
Jun 28 - Jul 3
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (1,000 reviews)
What a beautiful, unique building. Full of antiques and feels like going back in time. The ride up to my fourth floor room in the 19th century cage elevator was a wonderful touch. Can’t wait to go back again.
Reviewed on Apr 3, 2026
The Manchester View
Price was CA $1,417, price is now CA $1,159 per person
CA $1,159
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Albany (ALB)
9.4/10 Exceptional! (820 reviews)
Beautiful property, clean room, friendly staff. Will definitely be staying here again!
Reviewed on Mar 18, 2026
voco James Newbury Hudson Valley by IHG
Price was CA $1,830, price is now CA $1,595 per person
CA $1,595
per person
Jun 28 - Jul 3
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (350 reviews)
Beautiful property, friendly staff. Definitely will be back!!
Reviewed on Mar 29, 2026
Old Bennington Hotel Deals
The Four Chimneys Inn
21 West Road Bennington VT
The price is CA $301 per night from Apr 19 to Apr 20
CA $301
CA $328 total
Apr 19 - Apr 20
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $186 per night from May 3 to May 4
CA $186
CA $207 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Nice staff comfy bed nice views
Reviewed on Apr 8, 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $365 per night from Apr 14 to Apr 15
CA $365
CA $408 total
Apr 14 - Apr 15
includes taxes & fees
9.6/10 Exceptional! (610 reviews)
best hotel in the area
Reviewed on Apr 8, 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 Old Bennington
Vermont RT 100 Self 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.
