Bennington Vacation Packages 2025/2026 from $465

Bennington flight + hotel vacation packages

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

The Wiltwyck

per person

Sep 7 - Sep 11

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Albany (ALB)

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Hotel Brookmere & Arbor Spa

Save 100% on your flight

per person

Aug 7 - Aug 10

found 16 hours ago

Roundtrip flight included

Raleigh (RDU) to Albany (ALB)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Cornell Inn, Lenox & The Berkshires

per person

Aug 30 - Sep 1

found 1 day ago

Roundtrip non-stop flight included

Raleigh (RDU) 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.

The Equinox Golf Resort & Spa

per person

Aug 7 - Aug 10

found 16 hours ago

Roundtrip flight included

Raleigh (RDU) 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.

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Save 100% on your flight

per person

Sep 7 - Sep 11

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Albany (ALB)

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Top Bennington hotels deals

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$114 total

Aug 3 - Aug 4

Total includes 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 perks like free self parking.

Pool

Pet friendly

Hampton Inn Bennington

51 Hannaford Square, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$175 total

Jul 13 - Jul 14

Total includes 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

The Autumn Inn

924 East Main Street, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

Jul 8 - Jul 9

Total includes 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

Best Western Bennington

220 Northside Drive, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$133 total

Jul 13 - Jul 14

Total includes 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

$144 nightly

$157 total

Jul 15 - Jul 16

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, luggage storage, and concierge services are also on offer.

Pet friendly

Parking included

Harwood Hill Motel

864 Harwood Hill Road, Bennington, VT

$130 nightly

$142 total

Jul 8 - Jul 9

Total includes taxes and fees

This motel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and express check-in are also on offer.

Breakfast included

Pet friendly

Don't see what you're looking for?

See all available properties in Bennington

View all properties

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(71 reviews)

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Old First Congregational Church

5/5(4 reviews)

Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

4.5/5(2 reviews)

You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.

Frequently asked questions

How much are vacation packages to Bennington?

You can find an excellent flight and hotel bundle from just $465. 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.