Bennington County Vacations & Trips from $575
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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
Manchester
Bennington
Manchester Center
Wilmington
Dorset
Bondville
Arlington
East Dorset
The Latest Bennington County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Prospect Berkshires
$1,386
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Albany (ALB)
9.8/10 Exceptional! (40 reviews)
It was beautiful but quite expensive. There was no housekeeping included so trash was not picked up and the breakfasts were grossly overpriced!
Reviewed on Aug 19, 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
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
$110 nightly
$120 total
Sep 13 - Sep 14
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"The rooms are paper thin. And the cops get called there quite often for no reason."
Reviewed on Aug 20, 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! (862 reviews)
"A few unexpected extra charges for property fees"
Reviewed on Aug 17, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
$229 nightly
$252 total
Sep 7 - Sep 8
Total with taxes and fees
7.4/10 Good! (659 reviews)
"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."
Reviewed on Aug 16, 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 Bennington County attractions
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.
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.
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 family-friendly 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.
Equinox Preservation Trust
9.2/10 (100 reviews)
Enjoy the mountain views and explore Equinox Preservation Trust, a lovely green space in Manchester Center. Discover the spas in this family-friendly area, or seek out its hiking trails.
Bennington College
8.8/10 (43 reviews)
Explore the campus of Bennington College, during your travels in North Bennington. Attend a sporting event or discover the mountain views in this trendy area.
What to do in Bennington County
Vermont RT 100 App-Guided Driving Audio Tour
$17
per traveler
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