North Bennington Vacation Packages
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Your North Bennington Vacation
Our North Bennington vacation packages provide countless opportunities to indulge in new sights, sounds and tastes. And with all the finer details worked out, you can let go and enjoy your city break without a care in the world. You'll want to do some exploring during your trip to North Bennington. Drop by big-name attractions such as Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Don't put off your visit to this city any longer. The perfect North Bennington vacation is a few clicks away with Expedia.
Top North Bennington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CA $1,213, price is now CA $1,030 per person
CA $1,030
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
8.8/10 Excellent! (2,355 reviews)
The room was clean and spacious. The kitchen was equipped with all necessary supplies to cook a full meal. Great place to stay and relax or plan family fun!
Reviewed on May 24, 2026
The Yankee Inn
Price was CA $1,388, price is now CA $1,156 per person
CA $1,156
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Excellent value, I had a great experience. The breakfast was a cut above, but they didn't include any fresh fruit. Maybe that's nit-picking. I'd recommend it, especially to families. Lots of good restaurants nearby.
Reviewed on May 23, 2026
Berkshire Mountain Lodge
Price was CA $1,231, price is now CA $1,042 per person
CA $1,042
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (928 reviews)
The stay was great . No complains at all . Definitely will be staying in the near future .
Reviewed on May 22, 2026
Berkshires Untold
Price was CA $1,406, price is now CA $1,198 per person
CA $1,198
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (938 reviews)
Loved my stay here! The staff is friendly and helpful and the property is clean, comfortable and nicely appointed with a small bar and dining area. My room was spotless with an updated and spacious bathroom. The bed and linens were comfortable and there was a cozy reading chair as well. I loved the thoughtful decorative nods to the Berkshires and its history throughout. My only suggestion would be an adjustable desk chair as it was pretty low.
Reviewed on May 23, 2026
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was CA $1,221, price is now CA $1,076 per person
CA $1,076
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9.2/10 Wonderful! (894 reviews)
Wonderful stay for families.
Reviewed on May 22, 2026
North Bennington Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $213 per night from May 27 to May 28
CA $213
CA $237 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"I loved the use of space for local artists to display there art. Beautiful work. The hotel was very clean. Loved that you could get a coffee or water throughout the day. I wish that the pool was opened all day. Ample parking"
Reviewed on May 23, 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $389 per night from Jun 22 to Jun 23
CA $389
CA $434 total
Jun 22 - Jun 23
includes taxes & fees
9.6/10 Exceptional! (628 reviews)
"Great property and restaurant. Perfect location and very helpful, friendly staff."
Reviewed on May 23, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
The price is CA $229 per night from Jun 2 to Jun 3
CA $229
CA $306 total
Jun 2 - Jun 3
includes taxes & fees
9.4/10 Exceptional! (844 reviews)
"This is one of my favorite hotels. It’s close to restaurants but is also quiet with lots of cozy common space. It’s dog-friendly, has a great social hour and restaurant, and the morning coffee is delicious!"
Reviewed on May 23, 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.
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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.
