Bennington Vacation Packages 2026 from $311

Name: Hampton Inn Bennington
Price range: $151 total

Bennington flight + hotel vacation packages

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

Berkshire Mountain Lodge

$311

per person

Jun 19 - Jun 22

found 18 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

$707

per person

Jun 26 - Jun 29

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Albany (ALB)

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Hideaway Inn Lenox

$578

per person

Jun 30 - Jul 3

found 1 day ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.

Lodges At Cresthaven

Save 100% on your flight

$2,410

per person

Aug 10 - Aug 14

found 14 hours ago

Roundtrip flight included

New York (NYC) to Albany (ALB)

A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.

The Yankee Inn

$827

per person

Jun 26 - Jun 29

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) 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.

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

May 26 - May 27

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

Hampton Inn Bennington

51 Hannaford Square Bennington VT

$139 nightly

$151 total

Jun 14 - Jun 15

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

$116 nightly

$126 total

May 24 - May 25

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

The Autumn Inn

924 East Main Street Bennington VT

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$97 total

May 21 - May 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.

Harwood Hill Motel

864 Harwood Hill Road Bennington VT

Get rates

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

The Four Chimneys Inn

21 West Road Bennington VT

$247 nightly

$270 total

May 25 - May 26

Total with taxes and fees

A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A garden, a lobby fireplace, and a picnic area are also on offer.

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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.

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.

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 $311. 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.