
Deals on vacations and trips to Bennington
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Bennington flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.


Hotel Brookmere & Arbor Spa
Save 100% on your flight
per person
Aug 7 - Aug 10
found 16 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

The Cornell Inn, Lenox & The Berkshires
per person
Aug 30 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Raleigh (RDU) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

The Equinox Golf Resort & Spa
per person
Aug 7 - Aug 10
found 16 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
Top Bennington hotels deals

Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street, Bennington, VT
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $114 total per night
$114 total
Aug 3 - Aug 4
Total includes 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 perks like free self parking.
Pool
Pet friendly

Hampton Inn Bennington
51 Hannaford Square, Bennington, VT
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $175 total per night
$175 total
Jul 13 - Jul 14
Total includes 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

The Autumn Inn
924 East Main Street, Bennington, VT
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $97 total per night
$97 total
Jul 8 - Jul 9
Total includes 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.
Pet friendly
Parking included

Best Western Bennington
220 Northside Drive, Bennington, VT
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $133 total per night
$133 total
Jul 13 - Jul 14
Total includes taxes and fees
This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and express check-out are also on offer.
Pool
Breakfast included

South Shire
124 Elm St, Bennington, VT
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $157 total per night
$157 total
Jul 15 - Jul 16
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, luggage storage, and concierge services are also on offer.
Pet friendly
Parking included

Harwood Hill Motel
864 Harwood Hill Road, Bennington, VT
$130 nightly
The price is $142 total per night
$142 total
Jul 8 - Jul 9
Total includes taxes and fees
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
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(71 reviews)
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
5/5(4 reviews)
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.
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.
Frequently asked questions
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.
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