Bennington Vacation Packages 2026 from $422

Bennington flight + hotel vacation packages

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

Vacation Village in the Berkshires

$422

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This aparthotel features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

The Whitlock

Save 100% on your flight

$530

per person

Oct 2 - Oct 5

found 15 hours ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

Berkshire Mountain Lodge

$425

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

This aparthotel 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 Express & Suites Pittsfield-Lenox-Berkshires by IHG

$447

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

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

Berkshires Untold

$637

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Albany (ALB)

A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.

Top Bennington hotels deals

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$120 total

Aug 30 - Aug 31

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

Knotty Pine

130 Northside Dr Bennington VT

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$132 total

Aug 18 - Aug 19

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

New Englander Inn Bennington

220 Northside Drive Bennington VT

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$113 total

Sep 13 - Sep 14

Total with taxes and fees

A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, a picnic area, and express check-out are also on offer.

Breakfast included

Parking included

Hampton Inn Bennington

51 Hannaford Square Bennington VT

Free Cancellation

Reserve now, pay when you stay

$171 nightly

$187 total

Aug 23 - Aug 24

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

Starlight Inn

357 Us Route 7 S Bennington VT

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$103 total

Aug 18 - Aug 19

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and free newspapers are also provided.

Pet friendly

Parking included

Bennington Motor Inn

143 West Main Street Bennington VT

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$108 total

Aug 18 - Aug 19

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A library and free newspapers are also provided.

Parking included

Free WiFi

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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.

Stay near popular Bennington attractions

Bennington Battle Monument

9.0/10 (202 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.

See properties

Frequently asked questions

How much are vacation packages to Bennington?

You can find an excellent flight and hotel bundle from just $422. 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.