A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Bennington Holidays from £638

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Your Bennington Holiday

Our holiday packages to Bennington allow you to create your own adventure. Tailor your getaway to your interests and needs and make every moment count in this interesting city. Every trip to Bennington needs a well-planned itinerary. Fill yours with famous sights like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Don't put off visiting this city any longer. The ultimate Bennington holiday is only a few clicks away with Expedia.

Top Bennington flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 28 Jan - 1 Feb

    Berkshire Mountain Lodge + Flight

    Pittsfield
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,268 reviews)
    Return • Manchester (MAN) - Albany (ALB)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £723
    £638
    per traveller
    found 1 day ago
    Berkshire Mountain Lodge
  • 28 Jan - 1 Feb

    Vacation Village in the Berkshires + Flight

    Williamstown
    4 nights
    3.0 star property
    8.8/10 - Excellent (2,841 reviews)
    Return • Manchester (MAN) - Albany (ALB)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £771
    £667
    per traveller
    found 1 day ago
    Vacation Village in the Berkshires
  • 28 Jan - 1 Feb

    The Whitlock + Flight

    Lenox
    4 nights
    2.0 star property
    8.4/10 - Very good (417 reviews)
    Return • Manchester (MAN) - Albany (ALB)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £802
    £709
    per traveller
    found 1 day ago
    The Whitlock
  • 28 Jan - 1 Feb

    Hotel Downstreet, an Ascend Collection Hotel + Flight

    North Adams
    4 nights
    3.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    Return • Manchester (MAN) - Albany (ALB)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £830
    £777
    per traveller
    found 1 day ago
    Hotel Downstreet, an Ascend Collection Hotel
  • 28 Jan - 1 Feb

    Quality Inn Lee - Lenox South + Flight

    Lee
    4 nights
    2.5 star property
    8.6/10 - Excellent (1,005 reviews)
    Return • Manchester (MAN) - Albany (ALB)
    MAN - BOS • 1 stop BOS - MAN • 1 stop
    £684
    £644
    per traveller
    found 1 day ago
    Quality Inn Lee - Lenox South

Discover the most popular places to visit in Bennington

What to do in Bennington

Bennington Hotel Deals

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.

Frequently Asked Questions

Why should I book my Bennington holiday with Expedia?

Expedia has your back for every detail of your Bennington getaway. You'll always get the best deals, but when you bundle your flights, hotel and/or hire car into a holiday package, you'll get even bigger savings. Looking to really make the most of your adventure? Add some fun tours and activities to your package. Expedia offers flexible cancellation policies on almost all bookings, so you won't need to worry if your travel plans change. Visit our Customer Service Portal link to find out more.

When is the best time of year to holiday in Bennington?

Bennington can get very busy in January, February and July, so if you want to avoid the crowds, pack your bags for September, October and November. With average daytime temperatures of -6ºC, January is the coolest period in Bennington. The warmest month is July, when you can experience average temperatures of 21ºC throughout the day. Whatever the temperature, you'll find plenty of things to keep you entertained here.

What are the top hotels for my holiday in Bennington?

Paradise Inn in the Old Bennington neighbourhood is an excellent choice for a Bennington holiday. Check in here and you'll be perfectly placed to get out and discover all that this colourful city has to offer.

How do I get a cheap holiday to Bennington?

One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and hire cars — we've got them all. Pick and choose the combination that best fits you and see your savings grow. We know holidays are never a one-size-fits-all. That's why we offer over 400 partner airlines and 321,000 properties throughout the world, which lets you customise your Bennington holiday your way. Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.

What should I do on my Bennington holiday?

Make sure your next holiday in Bennington is one to remember by checking out its leading attractions. Bennington Battle Monument, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display, Prospect Mountain Cross-Country Ski Centre and Bennington Potters Yard are just a few of the things you should see while you're in this city.

What is the best area to stay in when on holiday in Bennington?

There's lots to explore in Bennington, so spend your nights close to its best attractions and maximise your time sightseeing. Bromley Mountain Ski Resort is one place to put on your must-see list.

Do I need a visa for my Bennington holiday?

Look up the latest rules on official government websites. Your nationality and whether you're travelling for business, study or leisure will determine if you need a visa for Bennington. Find out about the application process, including the required documentation, turnaround times and fees. Finalise your application well in advance to allow enough time for processing. Some visas may take weeks or even months to go through, depending on the country.

What should I wear on my Bennington holiday?

Although everyone's style is different, it can be useful to have some guidelines for what type of clothes to bring during your holiday in Bennington. Think about looking up social media before you head off for inspiration on local fashion trends. Check the weather forecast so you can pack appropriately. The warmest time of year in Bennington is July, with average daytime temperatures of 21ºC. If you plan to travel in the coolest month of January, the mercury averages -6ºC during the day.

What does an Expedia Bennington holiday include?

Flights, hotels and a shiny set of wheels for all your fun road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on some sightseeing tours and watch your savings pile up. When it comes to creating your Bennington trip, you're in charge! Discover a large range of property types and choose one that fits your group size and travel needs. The most sought-after rentals here are private holiday homes and cottages. With Expedia, you can easily design your Bennington escape however you like.

Does Expedia offer Book Now, Pay Later Bennington holidays?

Your bank balance shouldn't prevent you from taking a 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 your dream getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions works for you, Klarna offers just that! Paying in several transactions will make your getaway dreams come true.
  • No-deposit holidays: If no upfront fee for your getaway makes clicking that "book now" button easier, choose a no-deposit holiday plan from Klarna so you can Book Now, Pay Later!

Can I choose my airline with a Bennington Expedia holiday?

You can, and with more than 400 airlines to pick from throughout the world, you're not short on choice. Have a look through the available options and see which airline best suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.