Old Bennington Vacations from $893
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Your Old Bennington Vacation
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 personalized Old Bennington vacation 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 vacation to Old Bennington to suit your travel style, whatever that may look like.
The Latest Old Bennington vacation packages
Price found within the past 48 hours. Click for updated prices.
The Cornell Inn, Lenox & The Berkshires
$1,103
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf.
Reviewed on Oct 14, 2026
Brook Bound Inn
$1,333
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 2026
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View all tripsStay 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.
Bennington Museum
9.0/10 (50 reviews)
You can spend an afternoon studying the exhibits at Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and coffeehouses.
Old First Congregational Church
9.6/10 (12 reviews)
Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.
What to do in Old Bennington
Vermont RT 100 App-Guided Driving Audio Tour
$17
per traveler
Old Bennington Hotel Deals
The Four Chimneys Inn
21 West Road Bennington VT
$249 nightly
$271 total
Nov 1 - Nov 2
Total with taxes and fees
9.4/10 Exceptional! (291 reviews)
"Very nice, quiet place. Relaxing and cute."
Reviewed on Sep 7, 2026
The Williams Inn
101 Spring Street Williamstown MA
$206 nightly
$230 total
Nov 10 - Nov 11
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$163 nightly
$178 total
Nov 16 - Nov 17
Total with taxes and fees
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.
Find the Best Old Bennington Vacation Packages
Old Bennington Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Prospect Mountain Cross-Country Ski Center, Woodford State Park and Prospect Mountain Nordic Ski Center |
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Frequently asked questions
How much does an Old Bennington vacation package cost?
You'll find cheap prices from $893 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?
You can typically find lower prices and better availability in August, October and November. Take a look at our cheap Old Bennington vacation packages and you could land some excellent off-season deals.
How many days is enough for Old Bennington?
With a well-organized travel plan, you can easily tick off the top Old Bennington attractions in a few days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Old Bennington vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Old Bennington vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Old Bennington trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.