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Bennington Vacations

Your trip

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Hotel stay must be within date range of Leave and Return.

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Your Bennington vacation

From family vacations to last-minute romantic getaways, make Orbitz your first and only stop for Bennington vacations. You can customize your trip with flights, hotels and activities to match your travel plans and tastes. Sweeten the pot with extra savings when you book your flight and hotel together.

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Build your own Bennington vacation itinerary. Choose a flight that matches your schedule and a hotel with the amenities you need. Book them together for extra discounts you won't find when booking separately.

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Bennington Vacation Packages

Hotel only $100

1 BEST WESTERN PLUS New Englander Motor Inn

3 stars
4.0 / 5 22 reviews

220 Northside Drive Map

This charming Bennington, Vermont hotel provides convenient access to Bennington College and several local ski resorts. Discover the beauty and serenity of southern Vermont while staying at the BEST WESTERN PLUS New Englander Motor Inn. This Bennington hotel is ideal... More

Hotel only $129

2 Hampton Inn Bennington

3 stars
4.3 / 5 9 reviews

51 Hannaford Square Map

Free On The House hot breakfast, Wi-Fi

a true taste of New England...welcome to the Hampton Inn Bennington. The Hampton Inn® hotel in Bennington offers guests a quintessential taste of Vermont: the apples, the fall foliage, the old spire of a white clapboard church and plenty of Colonial architecture. From the... More

Hotel only $65

3 Bennington Motor Inn

2 stars
2.8 / 5 4 reviews

143 West Main Street Map

The Bennington Motor Inn is family owned and operated. All our guest rooms offer newly decorated, cozy colonial charm, and all modern conveniences including private shower baths, color cable television, air conditioning, touch-tone telephones individual heat thermostats,... More

4 Paradise Inn

2 stars
2.5 / 5 2 reviews

141 West Main Street Map

The Paradise Inn offers you 77 rooms, some of which include, private balconies, patios, Jacuzzi and sauna. Also available are suites and luxurious studios with full kitchens. The complex is surrounded by 8 acres of beautifully landscaped gardens including a heated outdoor... More

Hotel only $65

5 Midtown Motel

2 stars
1.5 / 5 2 reviews

107 W. Main St Map

The Midtown Motel is a familyowned motel conveniently located in Bennington Vermont. With its important place in Revolutionary War history Bennington is a great getaway destination offering a variety of attractions for visitors of all ages. The MidTown Motel is located... More

6 The Vermonter Motor Lodge

2 stars
2.8 / 5 12 reviews

2968 West Road Map

Flower strewn grounds set against a backdrop of Vermont's lush Green Mountains welcome you to our special part of the world, where natural beauty and gracious hospitality play equal parts in making your visit relaxing and enjoyable. Set against a backdrop of Vermont's... More

Hotel only $41

7 Alexandra B and B

3 stars
4.5 / 5 11 reviews

916 Orchard Road Map

An 1859 Vermont Farm House BB Inn with splendid views overlooking the Bennington Monument and Green Mountains of Vermont- the Alexandra BB Inn offers an elegant understated respite for weary business travelers or vacationing adventurers. Step inside and enjoy the... More