Deals on vacations and trips to Bennington

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Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

3.5 out of 5
Price was $419, price is now $341 per person
$341
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
South Shire

South Shire

4 out of 5
Price was $1,482, price is now $1,108 per person
$1,108
per person
Dec 26 - Jan 2
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, express check-in, and express check-out are also on offer.
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Manchester Village Historic District
Price was $1,743, price is now $1,424 per person
$1,424
per person
Dec 26 - Jan 2
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
Price was $933, price is now $773 per person
$773
per person
Dec 26 - Jan 2
found 15 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
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.
Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,173, price is now $979 per person
$979
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.

Top Bennington hotels deals

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $116 total per night
$116 total
Nov 15 - Nov 16
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
New Englander Inn Bennington

New Englander Inn Bennington

2.5 out of 5
220 Northside Drive Bennington VT
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $100 total per night
$100 total
Oct 25 - Oct 26
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.
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square Bennington VT
Free Cancellation
Reserve now, pay when you stay
$171 nightly
The price is $187 total per night
$187 total
Oct 25 - Oct 26
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

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $164 total per night
$164 total
Oct 19 - Oct 20
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
Bennington Motor Inn

Bennington Motor Inn

2 out of 5
143 West Main Street Bennington VT
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $86 total per night
$86 total
Oct 19 - Oct 20
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
Starlight Inn

Starlight Inn

2 out of 5
357 Us Route 7 S Bennington VT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $108 total per night
$108 total
Oct 19 - Oct 20
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.
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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 $341. 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

Photos of local treasures

Browse Bennington vacation photos for more inspiration

A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.
A mountainous landscape with autumn foliage, a prominent church spire, and a winding road.
A large, historic mansion with a symmetrical facade, a central entrance with a portico, and a well-manicured garden with flower beds and a lawn.
A silhouette of a person hiking with a backpack against a sunset sky.
A park with autumn trees, a picnic table, and a bench.

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