Bennington County Vacations & Trips from $1,092
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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 destinations in Bennington County
Wilmington
Manchester
Bennington
Manchester Center
Dorset
Bondville
Arlington
Shaftsbury
The Latest Bennington County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Cornell Inn, Lenox & The Berkshires
$1,092
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back.
Reviewed on Oct 12, 2026
Mountain Green Resort
$4,036
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
$3,712
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
9.2/10 Wonderful! (68 reviews)
Property was good. We founded a lot of cobble webs around the house. The stove was dirty when we used and made a horrible smell of burned. The guys next door were very loud at 3am and we couldn't sleep till they left around 5-6am. Will for sure be back if we have a chance. The place is well located around town and near lot os restaurants e attractions.
Reviewed on Oct 5, 2026
Find the Best Bennington County Vacation Packages
Bennington County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Albany Intl. Airport (ALB) |
Top Sights | Emerald Lake State Park, Lake Shaftsbury State Park and Woodford State Park |
Bennington County Hotel Deals
Aspen At Manchester
5669 Main Street Manchester Center VT
Fully refundableReserve now, pay when you stay
$147 nightly
$162 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (701 reviews)
"Overall, we enjoyed our stay at Aspen. The grounds are beautiful, the location is very convenient, and the rooms were clean. We also appreciated the nice quality towels and the generous supply of them. However, we were very disappointed by the inaccurate information provided in the Expedia listing. ..."
Reviewed on Oct 12, 2026
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
$113 nightly
$124 total
Nov 3 - Nov 4
Total with taxes and fees
9.4/10 Exceptional! (927 reviews)
"Beautiful room, very clean and new. It was very bare in the room though. Breakfast from 8-10 and we went at 9:40, it was wiped out with nobody refilling so make sure you go early. Next day we went early and it was delicious! Hot tub was amazing which we used both nights. Overall, the views are gorgeous ..."
Reviewed on Oct 12, 2026
The Equinox Golf Resort And Spa
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
$160 nightly
$176 total
Nov 11 - Nov 12
Total with taxes and 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.
Stay near popular Bennington County attractions
Mount Equinox
9.6/10 (43 reviews)
Enjoy beautiful views of rivers, lakes and valley communities as you motor along the skyline drive in the Green Mountain State.
Photo by Marc Stempel
Emerald Lake State Park
You can take time to visit Emerald Lake State Park during your travels to East Dorset. Discover the mountain views in this quaint area.
Bromley Mountain Ski Resort
8.8/10 (160 reviews)
Hit the slopes in Peru with a visit to Bromley Mountain Ski Resort. Discover the mountain views in this quaint area.
Hildene
9.4/10 (148 reviews)
You can learn about the history of Manchester Center with a trip to Hildene. Discover the mountain views in this quaint area.
Golf Club at Equinox
8.4/10 (29 reviews)
Enjoy a round of golf in Manchester at Golf Club at Equinox. Discover the mountain views while you're in the area.
Manchester Designer Outlets
8.6/10 (185 reviews)
You can search for that perfect souvenir at Manchester Designer Outlets during your stay in Manchester Center. Discover the mountain views while you're in the area.
Southern Vermont Arts Center
9.0/10 (26 reviews)
Enjoy an outing to Southern Vermont Arts Center during your stay in Manchester Center. Discover the mountain views while you're in the area.
Southern Vermont College
8.2/10 (22 reviews)
Explore the campus of Southern Vermont College, during your travels in Bennington. While you're here, you can savor the charming coffeehouses.
What to do in Bennington County
Vermont RT 100 App-Guided Driving Audio Tour
$17
per traveler
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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.
