Old Bennington Vacation Packages
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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.
Top Old Bennington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Lenox
CA $1,358
per person
Sep 26 - Oct 2
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8/10 Very good! (39 reviews)
Staff is non-existent. I did see some people cleaning rooms.
Self check-in and self-check-out. I was told it would be by text, but all instructions came by email, so I missed the check-out instructions. I was long gone when I saw it. No coffee in the morning is major!!! Better instructions for Roku TV and for the A/C split unit would be nice. Parking was insufficient, so I parked on the lawn the first night. Our room only had sheer curtains on a first floor. Privacy or room darkening shades would seem appropriate for a first floor room.
Close to town, nice to be able to walk instead of drive. Exterior is appealing. Front porch seating is nice. Our room was comfortable, bathroom was clean and functional.
Reviewed on Aug 24, 2026
Ready to book your vacation to Old Bennington?
Old Bennington Hotel Deals
The Four Chimneys Inn
21 West Road Bennington VT
CA $391
CA $426 total
Aug 31 - Sep 1
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 Jul 24, 2026
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
CA $136
CA $148 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very good! (1,009 reviews)
"The staff was incredibly helpful and the breakfast was homemade not powdered eggs. Down side was the walls were a bit thin. Rooms were well appointed and it’s in a great location. I was there to volunteer for a RAm event and a lot of us stayed there. Next year I would stay there again. Maybe we can ..."
Reviewed on Aug 21, 2026
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
CA $354
CA $396 total
Sep 14 - Sep 15
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 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
CA $24
per traveller
Frequently asked questions
How much does an Old Bennington vacation package cost?
Offering great value package deals from CA $788 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 — perfect for travellers wishing to save money.
How many days is enough for Old Bennington?
Usually, a handful of days is enough to go to the major attractions during your Old Bennington vacation. However, if you want to have some time to relax or take day trips, think about extending your trip.
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 travelling 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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
