Bennington County Vacation Packages 2026 from $999

Search vacation packages deals in Bennington County's top destinations

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

Manchester

Vacations

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

Bennington

Vacations

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

$999

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.

The Suites at Killington Center

Save 100% on your flight

$2,028

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.

Summit Lodge

$1,039

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.

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

Save 100% on your flight

$4,336

per person

Dec 19 - Dec 23

found 13 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.

Mountain Green Resort

$2,188

per person

Dec 19 - Dec 23

found 13 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Rutland (RUT)

An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.

Top Bennington County hotels deals

Aspen At Manchester

5669 Main Street Manchester Center VT

$127 nightly

$140 total

Nov 2 - Nov 3

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.

Pool

Pet friendly

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$105 total

Nov 3 - Nov 4

Total with taxes and fees

A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Pool

Breakfast included

The Equinox Golf Resort And Spa

3567 Main Street Manchester VT

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$177 total

Nov 2 - Nov 3

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.

Pool

Hot Tub

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$120 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a gym and an outdoor tennis court. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

$147 nightly

$161 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

The Palmer House Resort, an Ascend Collection Hotel

5383 Main St Manchester Center VT

Free Cancellation

$115 nightly

$127 total

Nov 2 - Nov 3

Total with taxes and fees

This smoke-free hotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the indoor pool and free perks like continental breakfast and free self parking. You'll appreciate the seasonal outdoor pool, bar/lounge, and free newspapers.

Pool

Hot Tub

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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.

See properties

Photos of local treasures

Browse Bennington County vacation photos for more inspiration

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 $999. 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.