Name: South Shire
Price range: $183

Bennington flight + hotel vacation packages

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

The Wiltwyck

per person

Jun 16 - Jun 20

found 14 hours ago

Roundtrip flight included

Jacksonville (JAX) to Albany (ALB)

Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.

Church Des Artistes Guest House

Roundout

Save 100% on your flight

per person

Jun 16 - Jun 20

found 14 hours ago

Roundtrip flight included

Jacksonville (JAX) to Albany (ALB)

This guesthouse features an area shuttle, free self parking, and free WiFi in public areas. Enjoy the free continental breakfast each morning. A business center, a terrace, and a garden are also on offer.

Brookmere

per person

Aug 1 - Aug 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Hasbrouck House

per person

Jun 16 - Jun 20

found 14 hours ago

Roundtrip flight included

Jacksonville (JAX) to Albany (ALB)

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free valet parking. Guests will appreciate freebies like continental breakfast and free self parking.

La Quinta Inn & Suites by Wyndham Latham Albany Airport

per person

Jul 5 - Jul 9

found 12 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Albany (ALB)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Top Bennington hotels deals

Hampton Inn Bennington

51 Hannaford Square, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$166

includes taxes & fees

$152 per night

Jun 1 - Jun 2

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 conference rooms, 24-hour business center, and express check-out. There's a gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Pet friendly

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$105

includes taxes & fees

$96 per night

May 25 - May 26

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

Parking included

Best Western Bennington

220 Northside Drive, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$118

includes taxes & fees

$108 per night

May 6 - May 7

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

Harwood Hill Motel

864 Harwood Hill Road, Bennington, VT

$142

includes taxes & fees

$130 per night

May 6 - May 7

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 Autumn Inn

924 East Main Street, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$97

includes taxes & fees

$89 per night

May 6 - May 7

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

South Shire

124 Elm St, Bennington, VT

Free Cancellation

Reserve now, pay when you stay

$183

includes taxes & fees

$167 per night

May 6 - May 7

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

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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(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.

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.