Bennington Vacation Packages 2026 from $498

Bennington flight + hotel vacation packages

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

Hampton Inn Albany-Wolf Road (Airport)

$498

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, and luggage storage are also on offer.

Hilton Albany

Downtown Albany

$776

per person

Apr 18 - Apr 21

found 24 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Albany (ALB)

This traditional hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like free train station pick-up.

Marriott Albany

$514

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Hyatt Place Albany/Downtown

Downtown Albany

$641

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Staybridge Suites Albany Wolf Rd-Colonie Center by IHG

Roessleville

$724

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and free perks like buffet breakfast and 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

$118 nightly

$129 total

Mar 19 - Mar 20

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.

Knotty Pine

130 Northside Dr Bennington VT

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$118 total

Mar 16 - Mar 17

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.

Hampton Inn Bennington

51 Hannaford Square Bennington VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$142 total

Mar 22 - Mar 23

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.

Best Western Bennington

220 Northside Drive Bennington VT

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$111 total

Mar 19 - Mar 20

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.

Harwood Hill Motel

864 Harwood Hill Road Bennington VT

$130 nightly

$142 total

Mar 15 - Mar 16

Total with 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.

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Woodford VT

Get rates

This cottage features barbecue grills.

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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(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.

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.

Woodford State Park

You can take time to visit Woodford State Park during your travels to Woodford.

Frequently asked questions

How much are vacation packages to Bennington?

You can find an excellent flight and hotel bundle from just $498. 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.