Old Bennington Holidays

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Your Old Bennington Holiday

With one of our holiday packages to Old Bennington, you'll discover countless opportunities for relaxation and adventure. There's a lot to enjoy, including its rich history and spectacular views. Make your trip to Old Bennington even more fun by including some sightseeing. Bennington College, Bennington Battle Monument and Hemmings Motor News Car Lovers Convenience Store & Vehicle Display are some of the top attractions you'll want to explore. Expedia can help you escape your routine. Tailor your holiday to Old Bennington to suit your style of travel, whatever that may be.

Old Bennington Holiday

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

Our pick of the best Old Bennington Hotel Deals

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road, Bennington, VT
Get rates
The Four Chimneys Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$259 per night from 28 Sept to 29 Sept
AU$259
28 Sept - 29 Sept
includes taxes & fees
Hotel Downstreet, Ascend Hotel Collection
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$356 per night from 22 Sept to 23 Sept
AU$356
22 Sept - 23 Sept
includes taxes & fees
9.6/10 Exceptional! (489 reviews)
"Beautiful atmosphere and grounds."

Reviewed on 26 Aug. 2025

The Williams Inn
See all 951 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Old Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

AU$26
per traveller
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Old Bennington

Frequently asked questions

How much does an Old Bennington holiday package cost?
You'll find cheap prices on Expedia for your Old Bennington escape. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your holiday to Old Bennington costs.
What are the cheapest months to go to Old Bennington?
January, March and August are great times to look for cheap Old Bennington holiday packages. Opting to travel in quieter periods means you can generally find better prices on flights and hotels.
How many days is enough for Old Bennington?
Typically, a handful of days is enough to visit the main sights during your Old Bennington holiday. However, if you prefer to have time to relax or go on day tours, consider extending your itinerary.
How to find the best Old Bennington package deals?
Use Expedia's filter tool to find some great Old Bennington package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Old Bennington package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book an Old Bennington holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can tailor your Old Bennington escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Old Bennington?
Land amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Old Bennington adventure.
How to plan a trip to Old Bennington?

  1. Pick your dates: What you want to do in Old Bennington and your favourite season will help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will likely be the biggest expense during your trip to Old Bennington.
  3. Work out your trip length: Consider how long you'd like to spend discovering Old Bennington. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick an Old Bennington holiday package that brings all your bookings together.

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