Name: South Shire
Price range: $183

Bennington flight + hotel vacation packages

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

Brookmere

per person

Jul 15 - Jul 18

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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 Ponds at Foxhollow

Save 100% on your flight

per person

Jul 20 - Jul 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

This condo resort features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a 24-hour front desk and laundry facilities.

Vacation Village in the Berkshires

per person

Jul 20 - Jul 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Lodges At Cresthaven

per person

Jun 6 - Jun 9

just found

Roundtrip non-stop flight included

Boston (BOS) to Albany (ALB)

A private beach, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

Save 100% on your flight

per person

Jul 20 - Jul 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

This cottage includes free WiFi in public areas and barbecue grills.

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

May 18 - May 19

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

$125

includes taxes & fees

$114 per night

May 18 - May 19

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 8 - May 9

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 7 - May 8

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 8 - May 9

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

Don't see what you're looking for?

See all available properties in Bennington

View all properties

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.