Bennington County Vacation Packages
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Your Bennington County Vacation
Set off on your next big adventure with a Bennington County vacation package, and leave relaxed knowing all the details are already organized. And with the ability to customize your escape, it'll be one to remember. With so many things to do and see on a trip to Bennington County, it can be tricky to know where to begin. Kick off your travels in Bennington at Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display — two much-loved attractions here. Another city worthy of a spot on your itinerary is Dorset. Don't miss Hildene and Vermont Summer Festival. When you're ready to stop dreaming and start doing, Expedia will help turn your Bennington County vacation into a reality.
Top Bennington County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Yankee Inn
Price was CA $896, price is now CA $711 per person
CA $711
per person
Jul 27 - Jul 30
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
9.2/10 Wonderful! (1,006 reviews)
Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff.
Reviewed on May 26, 2026
The Shire Woodstock
Price was CA $1,849, price is now CA $1,609 per person
CA $1,609
per person
Jun 26 - Jun 30
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (929 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants
Reviewed on May 12, 2026
Align Inn Vermont
Price was CA $1,551, price is now CA $1,460 per person
CA $1,460
per person
Jun 26 - Jun 30
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
9.4/10 Exceptional! (1,186 reviews)
There were some issues with the layout of the room, namely that the bathroom and the kitchen share the same space! There was a main room with beds, tv and chairs (no problems in this room), and then a dividing barn door. On the other side of the barn door was a sink. To the right of the sink was the toilet and shower, and to the left of the sink was the fridge, and counter space.
Another issue was that there was no designated sidewalk or walkway to the front door or lobby on the outside, so pedestrians had to walk with vehicles alongside. This is a potential safety issue, especially with little children.
Reviewed on May 27, 2026
Deer Brook Inn
Price was CA $1,720, price is now CA $1,630 per person
CA $1,630
per person
Jun 26 - Jun 30
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (1 review)
A beautiful location. Hosts were amazing. Clean and tastefully decorated. My only criticism would be to add ports for charging cell phones and computers. Otherwise, it was incredible. We highly recommend this location!
Reviewed on May 24, 2026
Woodstock Inn & Resort
Price was CA $2,705, price is now CA $2,700 per person
CA $2,700
per person
Jun 26 - Jun 30
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (578 reviews)
Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel.
Reviewed on May 22, 2026
Bennington County Hotel Deals
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
The price is CA $222 per night from Jun 16 to Jun 17
CA $222
CA $302 total
Jun 16 - Jun 17
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
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
The price is CA $182 per night from Jun 2 to Jun 3
CA $182
CA $278 total
Jun 2 - Jun 3
includes taxes & fees
7.4/10 Good! (629 reviews)
"It was a beautiful setting! Service was slow. Our room had a slight smell to it and the pull out couch was dirty. We were very hopeful and are very understanding. Sharing this input to help hotel improve their services."
Reviewed on May 26, 2026
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jun 14 to Jun 15
CA $147
CA $160 total
Jun 14 - Jun 15
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Most importantly, our room was clean, nice, and quiet. No problems within the room, and I thought they offered a pretty nice room configuration for a hotel of their price range. However, outside of the room, the amenities were a little disappointing. The pool was not maintained (to be fair, it might ..."
Reviewed on May 24, 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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
