Bennington County Vacation Packages 2026 from $624

Search vacation packages deals in Bennington County's top destinations

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Bennington County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Gedney Farm

$624

per person

Mar 19 - Mar 22

found 10 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.

Prospect Berkshires

$735

per person

Mar 19 - Mar 22

found 10 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.

The Dewey

$667

per person

Mar 19 - Mar 22

found 10 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

The Cornell Inn, Lenox & The Berkshires

$678

per person

Mar 19 - Mar 22

found 10 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Wilder House Berkshires

$657

per person

Mar 19 - Mar 22

found 10 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.

Top Bennington County hotels deals

Kimpton Taconic Hotel by IHG

3835 Main St. Manchester VT

Free Cancellation

$219 nightly

$241 total

Feb 23 - Feb 24

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Pet friendly

The Equinox Golf Resort & Spa

3567 Main Street Route 7A Manchester VT

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$208 total

Feb 1 - Feb 2

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

The Manchester View

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

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$118 total

Feb 4 - Feb 5

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 Palmer House Resort, an Ascend Collection Hotel

5383 Main St Manchester Center VT

Free Cancellation

$100 nightly

$110 total

Feb 22 - Feb 23

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

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

Feb 1 - Feb 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

Hampton Inn Bennington

51 Hannaford Square Bennington VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$142 total

Feb 1 - Feb 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

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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.

Photos of local treasures

Browse Bennington County vacation photos for more inspiration

View of Stratton Mtn from Bromley Mtn in Vermont. Early spring.

Burt Henry Covered Bridge over the Walloomsac River in Bennington, VT

One of my favorite old 1800s covered bridges I got to enjoy today was the silk bridge. You can still travel on it but it is only wide enough for one car at a time. A beautiful piece of history in Bennington, VT

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 $624. 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.