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
The price is SARĀ 960 per night from Aug 4 to Aug 5
SARĀ 960
SARĀ 1,046 total
4 Aug - 5 Aug
includes taxes & fees
9.4/10 Exceptional! (289 reviews)
"We enjoyed our stay."

Reviewed on 11 July 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 SARĀ 603 per night from Aug 16 to Aug 17
SARĀ 603
SARĀ 674 total
16 Aug - 17 Aug
includes taxes & fees
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

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Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
See all 1,015 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.

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 coffeehouses and its art scene while you're in the area.
See properties

Frequently asked questions

How much does an Old Bennington vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Old Bennington costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Old Bennington?
If you'd like to book a cheap Old Bennington vacation package, consider visiting in January, March and August. You'll generally find lower rates on accommodations and flights during these months ā€” perfect for travelers wishing to save money.
How to find the best Old Bennington package deals?
Bagging a cheap Old Bennington package deal is easy with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Old Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book an Old Bennington vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking hotels and flights separately. Better still, you can customize your Old Bennington trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Old Bennington?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Old Bennington trip.
How to plan a trip to Old Bennington?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the available activities will also help you decide when to visit Old Bennington.
  2. Budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Old Bennington.
  3. Decide how long to go away for: Now that you're up to speed on Old Bennington, you can figure out the perfect length of your vacation. Put together a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose an Old Bennington vacation package that brings all your bookings together.