Old Bennington Holidays

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Your Old Bennington Holiday

The rich history and spectacular views are just the start of the things Old Bennington has on offer. Experience the very best of this interesting city the way you want with a personalised Old Bennington holiday package. If your trip to Old Bennington includes a little sightseeing, check out famous attractions like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Expedia will help you escape the everyday. Tailor your holiday to Old Bennington to suit your travel style, whatever that may look like.

Old Bennington Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Prospect Mountain Cross-Country Ski Centre, Woodford State Park and Prospect Mountain Nordic Ski Centre

Top hotels in Old Bennington

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
The price is £206 per night from 4 Aug to 5 Aug
£206
4 Aug - 5 Aug
includes taxes & fees
9.4/10 Exceptional! (289 reviews)
"We enjoyed our stay."

Reviewed on 11 Jul 2026

The Four Chimneys Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is £133 per night from 16 Aug to 17 Aug
£133
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Every one was very helpful and friendly"

Reviewed on 15 Jul 2026

Hotel Downstreet, an Ascend Collection Hotel
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on 25 May 2026

Get rates
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
See all 1,016 properties in Old Bennington
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.
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Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.
See properties

What to do in Old Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

£13
per traveller
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Old Bennington

Frequently asked questions

How much does an Old Bennington travel package cost?
Customize your Old Bennington travel package from just . Pick from any combination of flights, hotels and rental cars to put together the getaway you've long been dreaming about. Remember to add on one or two experiences!
If I'm not able to travel, can I cancel my Old Bennington travel package?
Your situation can change in a flash, so yes. You may be able to amend or cancel your Old Bennington travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make changes, but your car rental company, hotel or airline may charge additional fees. Need more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Old Bennington?
You'll save loads of cash if you combine your flights, car rentals and hotels into an Old Bennington travel package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer over 550 airlines and 1,000,000 hotels globally, which means you'll always have plenty of options to choose from. Like to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Old Bennington holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has devised a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a fabulous getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you come across an unbeatable deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Old Bennington?
Stay where the action is. Many travellers book hotels around top attractions, such as Bennington Battle Monument, Southern Vermont College and Bennington Museum.
What are the top hotels in Old Bennington?
Get your escape off to a fantastic start by staying at Hampton Inn Bennington. It's one of most sought-after hotels in Old Bennington. Another option is Paradise Inn.
How far in advance should I book my Old Bennington holiday?
The earlier, the better. Airlines typically release flight tickets around a year prior to departure, and this is your chance to pick up some of the cheapest prices. Boss just told you to take some holiday time next week? No problem! Expedia are never short on fantastic bargains to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Old Bennington travel package include?
It all comes down to what type of escape you have in mind. Old Bennington travel deals can include hotels, flights and car rentals. You can mix and match to find the bundle that suits you. You can also add on activities and experiences after you've booked to land even bigger discounts.
What should I know before booking an Old Bennington travel package?
A travel package can be easier on the credit card than separately booking everything you need for your escape. For example, bundle your flights, hotels and rental cars and land a great deal. Whatever your holiday goals are, there's sure to be a package that matches your budget.
Can I choose my airline with an Old Bennington Expedia travel package?
Expedia has access to more than 550 airline partners worldwide, so you sure can! Simply select your favourite carrier and craft the perfect Old Bennington getaway.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.