Bennington Vacations 2025 from CA $833

Bennington flight + hotel packages

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

Brookmere

per person

May 16 - May 18

found 7 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Book a stay at this spa hotel in Saratoga Springs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Saratoga Race Course and Saratoga Performing Arts Center are located nearby.

Club Wyndham Bentley Brook

per person

Apr. 19 - Apr. 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.

DoubleTree by Hilton Schenectady Downtown

Seward Place

per person

Apr. 19 - Apr. 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Stay at this 4-star eco-certified hotel in Schenectady. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Museum of Innovation and Science are located nearby.

The Clocktower Hotel at Century House, Ascend Hotel Collection

per person

Apr. 19 - Apr. 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Book a stay at this business-friendly hotel in Cohoes. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.

Hilton Garden Inn Albany Airport

per person

Apr. 19 - Apr. 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Albany (ALB)

Stay at this 3-star business-friendly hotel in Latham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.

Top Bennington hotels deals

Best Western Bennington

220 Northside Drive, Bennington, VT

Free cancellation

Reserve now, pay when you stay

CA $152

CA $166 total

includes taxes & fees

19 Mar - 20 Mar

Stay at this hotel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bennington Battle Monument and Bennington Museum are located nearby.

Hampton Inn Bennington

51 Hannaford Square, Bennington, VT

Free cancellation

Reserve now, pay when you stay

CA $194

CA $212 total

includes taxes & fees

30 Mar - 31 Mar

Book a stay at this business-friendly hotel in Bennington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Bennington Battle Monument and Old First Congregational Church are located nearby.

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street, Bennington, VT

Free cancellation

Reserve now, pay when you stay

CA $158

CA $172 total

includes taxes & fees

19 Mar - 20 Mar

Book a stay at this ski hotel in Bennington. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Museum are located nearby.

Bennington Motor Inn

143 West Main Street, Bennington, VT

Free cancellation

Reserve now, pay when you stay

CA $174

CA $190 total

includes taxes & fees

10 Apr - 11 Apr

Stay at this motel in Bennington. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Harmon Hill are located nearby.

Harwood Hill Motel

864 Harwood Hill Road, Bennington, VT

CA $173

CA $189 total

includes taxes & fees

16 Mar - 17 Mar

Stay at this motel in Bennington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Robert Frost Stone House Museum and Bennington Battle Monument are located nearby.

Breakfast included

Pet-friendly

Starlight Inn

357 Us Route 7 S, Bennington, VT

Get rates

Stay at this hotel in Bennington. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Robert Frost Stone House Museum and Norman Rockwell Exhibition are located nearby.

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

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

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.

Prospect Mountain Cross-Country Ski Center

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 Vacations

Make new memories, have incredible adventures and tread the path less traveled — anything is possible in Bennington. But first, let us fill you in on a few basic facts about your next vacation destination!

To help get you oriented, Bennington sits 110 miles (177 kilometers) west of the well-known city of Boston.

Eager to meet the locals? That shouldn't be an issue. 9,000 people call this part of Southern Vermont home.

Hotels in Bennington

Preparing to venture down the path less traveled in Bennington? Before you head on that extraordinary adventure, you'll need a place to rest and relax. Chose from Travelocity's 12 properties and get your vacation off to a sensational start.

On the hunt for somewhere to get some rest in Bennington? The Safford Mills Inn and Cafe and The Four Chimneys Inn are some of our favorite properties in the region.

Places to visit in Bennington

It has been said that knowledge is power. With that in mind, you'll certainly feel more powerful after spending an afternoon at Bennington Museum. Like some more options? Bennington Battle Monument stands as a reminder of history. Discover why this commemorative piece was built and gain more insight into the local heritage and achievements. And there's more. Get ready to encounter exciting ideas and wonderful artwork at Fiddlehead at Four Corners. It maintains a rotating roster of collections that are sure to interest art enthusiasts.

Where do you fly into for Bennington?

Pull on your headphones and watch one of the latest in-flight films. Before long, you'll be coming in to land at Albany International Airport (ALB). It's approximately 30 miles (48 kilometers) from the middle of Bennington.

Frequently asked questions

How much are vacation packages to Bennington?

You can find an excellent flight and hotel bundle from just CA $833. 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.