Old Bennington Vacations

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Find the Best Old Bennington Vacation Packages

Old Bennington Hotel Deals

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road, Bennington, VT
9.6/10 Exceptional! (219 reviews)
Perfection!!
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite."

Reviewed on Aug 20, 2025

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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 ￥21,108 per night from Sep 22 to Sep 23
￥21,108
￥23,579 total
Sep 22 - Sep 23
includes taxes & fees
8.6/10 Excellent! (999 reviews)
"Great stay. Well balanced, clean, friendly."

Reviewed on Aug 20, 2025

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 ￥29,798 per night from Sep 22 to Sep 23
￥29,798
￥33,285 total
Sep 22 - Sep 23
includes taxes & fees
9.6/10 Exceptional! (487 reviews)
"Great stay"

Reviewed on Aug 21, 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.

Discover the most popular places to visit in Old Bennington

Bennington Battle Monument showing landscape views

Bennington Battle Monument

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument

Bennington Potters Yard

You can do some window-shopping at Bennington Potters Yard during your stay in Bennington. Discover the coffeehouses and its art scene while you're in the area.

Bennington Potters Yard

Frequently asked questions

How much does an Old Bennington vacation 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 vacation 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 vacation 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 vacation. 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 vacation package as soon as possible.
Is it cheaper to book an Old Bennington vacation as a package?
An Expedia vacation 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 vacation 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 favorite 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 accommodations 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 vacation 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.