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Bennington flight + hotel packages

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Super 8 by Wyndham Cobleskill NY

Super 8 by Wyndham Cobleskill NY

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this golf hotel in Cobleskill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cobleskill Fairgrounds and Iroquois Indian Museum are located nearby.
Super 8 by Wyndham Albany

Super 8 by Wyndham Albany

2 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this family-friendly hotel in Kingston. Enjoy free breakfast, free parking, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dietz Stadium and Birch Body Care are located nearby.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel

Holiday Inn Express Hotel & Suites West Coxsackie, an IHG Hotel

2.5 out of 5
per person
Jan. 21 - Jan. 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
Book a stay at this business-friendly hotel in West Coxsackie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Parks Dairy and Bronck Island are located nearby.

Top Bennington hotels deals

The Hotel Vervana at Bennington

The Hotel Vervana at Bennington

2.5 out of 5
141 West Main Street, Bennington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $192 total
includes taxes & fees
26 Nov - 27 Nov
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.
Pool
Parking included
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
The price is CA $125 per night
CA $125
CA $136 total
includes taxes & fees
17 Nov - 18 Nov
Stay at this motel in Bennington. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Norman Rockwell Exhibition and Robert Frost Stone House Museum are located nearby.
Pet-friendly
Parking included
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square, Bennington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $196 per night
CA $196
CA $214 total
includes taxes & fees
8 Dec - 9 Dec
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.
Pet-friendly
Parking included
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $144 per night
CA $144
CA $157 total
includes taxes & fees
26 Nov - 27 Nov
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.
Pool
Breakfast included
Bennington Motor Inn

Bennington Motor Inn

2 out of 5
143 West Main Street, Bennington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
CA $184 total
includes taxes & fees
14 Dec - 15 Dec
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

Harwood Hill Motel

2 out of 5
864 Harwood Hill Road, Bennington, VT
The price is CA $168 per night
CA $168
CA $183 total
includes taxes & fees
20 Nov - 21 Nov
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.
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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 featuring landscape views

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.

Bennington Battle Monument
Old First Congregational Church

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.

Old First Congregational Church

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.

Prospect Mountain Cross-Country Ski Center

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 $570. 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.

Photos of local treasures

Browse Bennington vacation photos for more inspiration

Bennington Battle Monument featuring landscape views