North Bennington Historic District Vacations from $518
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Your North Bennington Historic District Vacation
Immerse yourself in all this neighborhood has to offer with a customized North Bennington Historic District vacation package. However you imagine yourself spending your time here, you'll find countless opportunities for adventure, relaxation and fun. Love to sightsee? Bennington College and Park McCullough House are two nearby attractions to swing by during your trip to North Bennington Historic District. Don't just wish for it — take action! Book your perfect North Bennington Historic District vacation with Expedia and travel your way.
The Latest North Bennington Historic District Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort
$518
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (946 reviews)
My wife and i went up to the area for a family wedding. we decided to stay at this hotel/resort - boy were we surprised on how nice it was. Everything from the check in process to the check out, things went very well. we stopped by the activities center on our second day and boy there were a lot of things to do with your kids. the indoor pool, the outdoor pool and other places were very nice and well maintained. We were happy with our room as well. We were upgraded to a two level villa - wow was that a lot of space. we had a full kitchen with a full fridge. we were very happy with that. Overall, we loved this resort and are looking forward going back next time we are in the area. I highly recommend this resort to all. Thank you for a great weekend.
Reviewed on Aug 14, 2026
Prospect Berkshires
$1,293
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.8/10 Exceptional! (40 reviews)
Once I got the cabin I expected it was an amazing stay.
Right on the water as shown on the website.
I look forward to my next stay.
Reviewed on Aug 1, 2026
North Bennington Historic District Hotel Deals
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
$110 nightly
$120 total
Aug 30 - Aug 31
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"The staff was great and welcoming. The room was comfortable and clean. The shower was strong and wonderful. The hotel was walking distance to pubs and restaurants. Overall a great night."
Reviewed on Aug 14, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
$257 nightly
$283 total
Sep 9 - Sep 10
Total with taxes and fees
9.4/10 Exceptional! (860 reviews)
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Reviewed on Aug 3, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
$140 nightly
$157 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Great location, spacious room, staff friendly and helpful."
Reviewed on Aug 15, 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.
Stay near popular North Bennington Historic District attractions
Park McCullough House
6.0/10 (1 review)
Find out about the history of North Bennington with a stop at Park McCullough House. Discover the mountain views and coffeehouses in this relaxing area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.