Deals on vacations and trips to Bennington County

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A white building with black shutters, a sign for Covey & NY, and an American flag.

Manchester

Vacations
Manchester
A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington

Vacations
Bennington

Bennington County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,306, price is now $989 per person
$989
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Summit Lodge

Summit Lodge

3 out of 5
Price was $1,354, price is now $1,029 per person
$1,029
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
This smoke-free hotel features 2 outdoor pools, a hot tub, and a restaurant. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $2,653, price is now $2,018 per person
$2,018
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services, barbecue grills, and a virtual front desk are also on offer.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,445, price is now $1,137 per person
$1,137
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay

3 out of 5
Save 100% on your flight
Price was $5,486, price is now $4,336 per person
$4,336
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

Stay near popular Bennington County attractions

A mountain with autumn foliage.

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.
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Photos of local treasures

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A house on a grassy hill surrounded by autumn-colored trees.
A statue with outstretched arms and a tall obelisk in the background.
A snow-capped mountain with a forested foreground and a cloudy sky.
A red covered bridge over a river, surrounded by greenery and trees.
A red covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 6 ft.

Frequently asked questions

How much are vacation packages to Bennington County?
With Travelocity vacation packages, you can be living it up in Bennington County for only $989. Flights, tours and hotels — we've got you covered. You can save some cash just by bundling together your bookings. With everything taken care of before leaving, you won't have a care in the world.
Where can I get the best vacation package deals for Bennington County?
It's simple — look no further than Travelocity. With as many as 400 airlines and 1,000,000 worldwide properties, it's a breeze to craft a Bennington County package deal that satisfies your wanderlust.
Why should I purchase my Bennington County vacation package via Travelocity?
Incredible savings, an abundance of breathtaking destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.
Can I save on my Bennington County car rental if I bundle it with my hotel or flight?
Combining your bookings into a Bennington County vacation package will leave you with a nice chunk of spare change. You can book a flight and car; a flight, hotel and car; or a hotel and car. You won't find a better way to explore the greater Bennington County area than with your own ride. You can also add experiences and activities to your Travelocity package.
What is the best time of year to go to Bennington County?
Vacationing in the quieter months of the year, March, April and November, comes with a few upsides — think better-value airfares and hotels and less pushing past throngs of tourists. But there's magic in the air during the high season. More events will be planned and more attractions will be open in January, June and August. If you're traveling on a budget, has the thriftiest hotel rates. You'll pay more for a bed in .
Which airport is best for Bennington County?
Flying to Bennington County means you'll step off the plane at Albany Intl. Airport (ALB) or Rutland Southern Vermont Regional Airport (RUT).
What is there to do in Bennington County?
A vibrant and lively destination, Bennington County offers some incredible tourist attractions. Bromley Mountain Ski Resort and Vermont Summer Festival are some of the favorites.

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