Bennington Vacation Packages 2026 from $529

Bennington flight + hotel vacation packages

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

Vacation Village in the Berkshires

$529

per person

Jul 18 - Jul 20

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Albany (ALB)

This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Seesaw's Lodge

$797

per person

Aug 22 - Aug 25

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Albany (ALB)

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

The Yankee Inn

$651

per person

Jul 18 - Jul 20

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Albany (ALB)

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Kimpton Taconic Hotel by IHG

Manchester Village Historic District

$919

per person

Aug 22 - Aug 25

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Albany (ALB)

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.

The Equinox Golf Resort & Spa

Manchester Village Historic District

$687

per person

Aug 22 - Aug 25

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Albany (ALB)

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.

Top Bennington hotels deals

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$128 total

Jun 29 - Jun 30

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

The Autumn Inn

924 East Main Street Bennington VT

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

Jun 21 - Jun 22

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Pet friendly

Parking included

Hampton Inn Bennington

51 Hannaford Square Bennington VT

Free Cancellation

Reserve now, pay when you stay

$142 nightly

$155 total

Jul 5 - Jul 6

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

Knotty Pine

130 Northside Dr Bennington VT

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$168 total

Jun 21 - Jun 22

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this motel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A communal living room, express check-in, and express check-out are also on offer.

Pool

Breakfast included

New Englander Inn Bennington

220 Northside Drive Bennington VT

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$139 total

Jul 9 - Jul 10

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and express check-out are also on offer.

Pool

Breakfast included

South Shire

124 Elm St Bennington VT

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$231 total

Jun 21 - Jun 22

Total with taxes and fees

A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.

Pet friendly

Parking 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.

Popular places to visit

Bennington Battle Monument

4.5/5(72 reviews)

After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the coffeehouses and its art scene while you're in the area.

Prospect Mountain Cross-Country Ski Center

4.5/5(11 reviews)

Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.

Bennington Museum

4.5/5(11 reviews)

You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.

Frequently asked questions

How much are vacation packages to Bennington?

You can find an excellent flight and hotel bundle from just $529. With one of our Travelocity vacation packages, an escape to Bennington has never been more tempting! Save both time and money and then start packing those bags.

How long should my Bennington vacation be?

Many travelers pack their bags and kick back in Bennington for about 2 nights. That gives you a rough guide, but don't be restricted by it. Whether you only stay a couple of nights to see the big attractions or hang around to explore new places, an epic adventure awaits.

Where can I get the best vacation package deals for Bennington?

There are awesome Bennington package deals waiting for you with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the world? Keep that in mind when you're ready to tick another place off your must-visit list.

Why should I book my Bennington vacation bundle with Travelocity?

The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.

Can I save money on my Bennington car rental if I book it with hotels and flights?

Combining your bookings into a Bennington vacation package will certainly save you money. Combine a flight and car; a flight, hotel and car; or a car and hotel. There's no better way to discover the greater Bennington region than from behind the wheel of your own rental car. You can also add experiences and tours to your Travelocity package.

What is there to do in Bennington?

While getting off the beaten track can be rewarding, you really shouldn't miss the big sights that make a place famous. Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display are just two of them in Bennington.

Where should I stay when visiting Bennington?

Many travelers opt to stay at the Hampton Inn Bennington. It's a great base for your Bennington escape.

Where to stay in Bennington: Best areas for travelers

Winhall: All aboard the Bennington express — this neighborhood is your first stop! Whether it's because of its good restaurants, many sights or its undeniable "je ne sais quoi," this neighborhood is the first choice for many visitors. Book a room at the Lovely Ski Chalet 1 Mile From Stratton Mountain Access Rd Many Update or the Large Contemporary Vt New Home and take your time exploring one of the city's undisputed highlights.
Shaftsbury: This neighborhood's unique character is one of the many reasons visitors return time and again. The Governor's Rock Motel and the Shaftsbury Vermont Farm House Full Of History, Views, And Classic Beauty are two hotel options to look into here.