Bennington County Vacations & Trips from $296
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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
Bennington
The Latest Bennington County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Schenectady Downtown
Seward Place
Price was $423, price is now $296 per person
$296
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (955 reviews)
Breakfast was good and seating was comfortable. Staff was cheerful all around. Room was comfortable and ironing board and iron was convenient and a life-saver.
Reviewed on Sep 26, 2025
DoubleTree by Hilton Schenectady Downtown
Seward Place
Price was $440, price is now $305 per person
$305
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.4/10 Very Good! (688 reviews)
Staff was friendly and they had warm cookies at check in. The food at the restaurant/bar was very good! The bartender was awesome with great service!
Reviewed on Sep 15, 2025
The Shire Woodstock
Price was $495, price is now $363 per person
$363
per person
Oct 31 - Nov 2
found 6 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.8/10 Excellent! (823 reviews)
Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river.
Reviewed on Sep 25, 2025
The Constance by the Lenox Collection
Price was $506, price is now $388 per person
$388
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.4/10 Very Good! (542 reviews)
Older inn in fair condition. Staff friendly. Very good breakfast w/fruit, yogurt, pastries etc. Shower curtain structure for claw foot tub is leaky and unstable and caused water to spray everywhere. Reported at check out. Nail clippings on desk when we first walked in. Nightstand lightbulb flickering and reported on arrival. Bed very comfortable. Good choice for one night but would research other options if returning to area again.
Reviewed on Sep 24, 2025
Bennington County Hotel Deals
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $189 total per night from Oct 26 to Oct 27
$189 total
Oct 26 - Oct 27
Total with taxes and fees
7.2/10 Good! (533 reviews)
"Such a beautiful location! Especially love the fire pit outside of the Falcon Bar"
Reviewed on Sep 24, 2025
Hampton Inn and Suites Manchester
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Oct 26 to Oct 27
$149 total
Oct 26 - Oct 27
Total with taxes and fees
9.6/10 Exceptional! (1,010 reviews)
"This was one of the best hotel experiences in this range I’ve ever had. Clean, well thought out, and comfortable room and building. Staff were all consistently engaged and friendly."
Reviewed on Sep 25, 2025
Kimpton Taconic Hotel by IHG
3835 Main St., Manchester, VT
Fully refundable
$298 nightly
The price is $328 total per night from Oct 23 to Oct 24
$328 total
Oct 23 - Oct 24
Total with taxes and fees
9.2/10 Wonderful! (803 reviews)
"Great checkout. Friendliness."
Reviewed on Sep 2, 2025
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.