
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.

Vacation Village in the Berkshires
per person
Aug 28 - Sep 1
found 9 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
This condo 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.

Four Points by Sheraton Albany
per person
Sep 26 - Sep 28
found 21 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a grocery/convenience store are also offered.

Hilton Garden Inn Albany Airport
per person
Sep 26 - Sep 28
found 21 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free area shuttle.

Hyatt Place Albany/Downtown
Downtown Albany
per person
Sep 26 - Sep 28
found 21 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Renaissance Albany Hotel
Downtown Albany
per person
Sep 26 - Sep 28
found 21 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a garden, and a hair salon are also offered.
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 17 - Aug 18
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 27 - Jul 28
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 20 - Jul 21
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 27 - Jul 28
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
$149 nightly
The price is $163 total per night
$163 total
Jul 23 - Jul 24
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
$135 nightly
The price is $147 total per night
$147 total
Jul 20 - Jul 21
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.
Photos of local treasures
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