Bennington Vacations

Hotel options

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.

Create your own Bennington travel plans
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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Scope out your Bennington vacation options and savings
With the Orbitz Matrix Display, you can view all your flight and hotel options quickly. Plus, you'll see what you can save on your travel packages when you book them together.
 

Bennington Vacation Packages

Free Cancellation
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51 Hannaford Square Map
4.3 / 5 12 reviews
  • Free On The House hot breakfast, Wi-Fi
  • Free On The House hot breakfast, Wi-Fi
Hotel only
$142

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
$142
Free Cancellation
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222 Adams Rd Map
4.3 / 5 18 reviews
Hotel only
$117

This old english property is located in the beautiful Berkshire Mountains in Williamstown MA. The Orchards Hotel a charming luxury hotel is built around a peaceful courtyard with a pond which can be viewed from many of our 49 beautifully appointed guest rooms and suites... More

Hotel only
$117
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213 Main Street Map
3.0 / 5 36 reviews
  • Save 10% on your stay
  • Save 10% on your stay
Hotel only
$44

Find family fun at this Howard Johnson Williamstown ideally located in the foothills of the Berkshire Mountains near Tanglewood. Tour the historic campus of Williams College, and view the art collections at Sterling and Francine Clark Art Institute and Massachusetts... More

Hotel only
$44
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231 River St Map
4.5 / 5 13 reviews
Hotel only
$119

accent contemporary pieces. Artwork is predominately paintandbyandnumber paintings from the 50ands and 60ands. Bedspreads are a distinctive whiteandonandwhiteand toned patchwork created by a local designer. The reception building includes two living roomsand one with a... More

Hotel only
$119
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89 Mountain Road Map
3.6 / 5 7 reviews
Hotel only
$184

Mount Snow Condominiums is the on-site rental manager at Mount Snow. We represent 7 condo complexes located slopeside base area or within 1 mile of the base of Mount Snow. Guests of Mount Snow Condos are permitted to use the amenities at the Grand Summit Hotel at no... More

Hotel only
$184
Free Cancellation
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220 Northside Drive Map
4.0 / 5 23 reviews
Hotel only
$109

This charming Bennington, Vermont hotel provides convenient access to Bennington College and several local ski resorts. 100% Non Smoking Rooms Discover the beauty and serenity of southern Vermont while staying at the BEST WESTERN PLUS New Englander Motor Inn. This... More

Hotel only
$109
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141 West Main Street Map
2.5 / 5 2 reviews

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

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143 West Main Street Map
2.8 / 5 4 reviews

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

Free Cancellation
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480 Main Street Map
3.6 / 5 25 reviews
Hotel only
$66

The Willows Motel, a non-smoking AAA 2 diamond rated Magnuson Hotels affiliate, is less than 5 miles from Massachusetts Museum of Contemporary Art and Mohawk Trail. Jiminy Peak Mountain Resort 15 miles, Tanglewood 30 miles, and the Norman Rockwell Museum 38 miles. We are... More

Hotel only
$66
Free Cancellation
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89 Mountain Road Map
3.7 / 5 9 reviews
Hotel only
$243

Located at the base of Mount Snow the Grand Summit Resort Hotel offers hotel rooms studios and multi-room suites with full-service kitchenettes to accommodate you and your family. Enjoy a full menu of spa services work out in the health club or relax in the outdoor... More

Hotel only
$243

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  • Promo Code Terms and Conditions

    50VACA
    Book a qualifying 4-night flight + hotel vacation package between January 1, 2014 12:00AM CT and March 31, 2016 11:59PM CT, for $1000 or more for travel between January 1, 2014 and June 30, 2016, via Orbitz and instantly receive $50 off the hotel portion of your booking through the use of the promotion code. Limit one discount per hotel room and one promotion code per booking. Discounts are not redeemable for cash for any reason. Promotion codes cannot be resold. Any attempt at fraud will be prosecuted to the fullest extent of the law. Void where prohibited, taxed or restricted. Orbitz reserves the right to change or limit the promotion in its sole discretion.