Old Bennington Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿27,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Old Bennington
The Four Chimneys Inn
21 West Road Bennington VT
฿8,460
฿9,221 total
18 Aug - 19 Aug
includes taxes & fees
9.4/10 Exceptional! (290 reviews)
"Room was clean. Staff helpful. Didn’t get a chance to have breakfast either days, the system of pre filled form for breakfast didn’t work for us. Didn’t get a chance to go to the bar"
Reviewed on 24 Jul 2026
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
฿3,630
฿3,957 total
30 Aug - 31 Aug
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"The room was somewhat spartan, but overall comfortable, and the beds were good. Unfortunately, the Internet connection was quite weak. The bathroom was small and somewhat awkwardly designed, as it was impossible to turn on the shower without stepping under cold water first. There was also a rather ..."
Reviewed on 11 Aug 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
฿4,639
฿5,182 total
2 Sept - 3 Sept
includes taxes & 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.
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 cafes and its art scene while you're in the area.
Bennington Museum
9.0/10 (50 reviews)
You can spend an afternoon exploring the galleries in Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and cafes.
Old First Congregational Church
9.6/10 (12 reviews)
Find out about the history of Old Bennington when you spend time 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
฿562
per traveller
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?
- Pick your dates: What you want to do in Old Bennington and your favourite season will help you decide when to travel.
- 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.
- 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.
- 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.
