Bennington Vacations

Hotel options

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

Room 1
*Ages of children at time of trip (for pricing, discounts)


Earn up to 5% on hotels and 1% on flights - It's free!

By clicking, I agree to the terms and conditions.

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.

Find Bennington travel discounts
Be the first to know about exclusive offers and last-minute deals on Bennington travel. Sign for our deals e-mail , or follow us on Twitter and Facebook for promo codes, discounts and more. Our global network of travel experts find big-time savings and travel deals just for you.

Get Bennington travel support 24/7
Reach out to an Orbitz travel specialist for Bennington vacation assistance. Our specialists are available around the clock at 1-800-504-3248. We can even help with last-minute Bennington vacations.

Sign up for free Bennington travel alerts
Make travel plans smoother with Orbitz Care Alerts. Receive real-time info about flight delays, weather and other events via phone, e-mail or text. Keep up to six other people in the loop with travel alerts, too.

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 Hotels

From $175

1 Hampton Inn Bennington

3 stars
4.3 / 5 11 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

From $154

2 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. 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

From $56

3 Howard Johnson Williamstown

2 stars
3.1 / 5 37 reviews

213 Main Street Map

Stay 2, Save 15%

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

From $130

4 Holiday Inn BERKSHIRES

3 stars
3.8 / 5 20 reviews

40 Main Street Map

The Holiday Inn Hotel Berkshires in Western Massachusetts has beautifully appointed guest rooms. We are nestled in the heart of the Berkshires, the ideal choice to explore all the Berkshire museums, theatres, historic sites and outdoor activities. Conveniently located in... More

From $120

5 Midtown Motel

1 star
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

From $142

6 Grand Summit Hotel

3 stars
3.6 / 5 7 reviews

89 Mountain Road Map

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

7 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

8 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

From $57

9 Green Valley Motel Williamstown

1 star
3.0 / 5 4 reviews

1214 Simonds Road Route 7 Map

On historic Route 7 and 2 miles North of the center of Williamstown, and the Williams College campus, the Green Valley Motel offers its guests simple, clean, comfortable rooms with modern amenities at reasonable rates. The Green Valley Motel is near Massachusetts College... More

From $69

10 The Vermonter Motor Lodge

2 stars
2.7 / 5 11 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

  • Promo Code Terms and Conditions

    Book a qualifying 4+ night flight + hotel vacation package between July 24, 2015 12:00AM CT and September 30, 2015 11:59PM CT, for $1000 or more for travel between July 24, 2015 and December 31, 2015 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. Promo code not valid for Las Vegas, NV bookings.

Sign up to receive our best deals

Get insider access to our best hotel deals, coupons and more!