Bennington Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Bennington Vacation
Our vacation packages to Bennington allow you to create your own adventure. Tailor your getaway to your interests and needs and make every moment count in this interesting city. Every trip to Bennington needs a well-planned itinerary. Fill yours with famous sights like Bennington College, Hemmings Motor News Car Lovers Convenience Store & Vehicle Display and Bennington Battle Monument. Don't put off visiting this city any longer. The ultimate Bennington vacation is only a few clicks away with Expedia.
Top Bennington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Aspen At Manchester
CA $1,084
per person
Oct 22 - Oct 25
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (683 reviews)
Absolutely loved this property! Amazing location, super clean and spacious rooms! We loved being in close proximity to the town, which was soooooo amazingly pet friendly! We will definitely be back
Reviewed on Sep 14, 2026
Ready to book your vacation to Bennington?
Bennington Hotel Deals
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
CA $137
CA $150 total
Sep 27 - Sep 28
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"Helpful staff, but property shows its age."
Reviewed on Sep 14, 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
CA $176
CA $192 total
Sep 20 - Sep 21
includes taxes & fees
Bennington Motor Inn
143 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
CA $131
CA $142 total
Sep 27 - Sep 28
includes taxes & fees
7.6/10 Good! (493 reviews)
"Roadside motor inn. Outdated, priced right, safe and reasonably clean for its age."
Reviewed on Sep 13, 2026
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 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.
Southern Vermont College
8.2/10 (22 reviews)
Explore the campus of Southern Vermont College, during your travels in Bennington. While you're here, you can savor the charming coffeehouses.
Prospect Mountain Cross-Country Ski Center
9.0/10 (28 reviews)
Hit the slopes in Woodford with a visit to Prospect Mountain Cross-Country Ski Center. In the area, take in the festivals and mountain views.
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.
Woodford State Park
8.8/10 (11 reviews)
You can take time to visit Woodford State Park during your travels to Woodford.
Bennington Center for the Arts
8.6/10 (22 reviews)
Enjoy an outing to Bennington Center for the Arts during your stay in Bennington. Experience the area's art scene and museums.
Bennington Potters Yard
8.0/10 (11 reviews)
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.
Robert Frost Stone House Museum
9.2/10 (15 reviews)
You can spend an afternoon exploring the galleries in Robert Frost Stone House Museum during your trip to Bennington. Discover the area's charming coffeehouses and its fascinating museums.
What to do in Bennington
Vermont RT 100 App-Guided Driving Audio Tour
CA $24
per traveller
Frequently asked questions
How much does a Bennington vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,084 on Expedia. But how much your vacation to Bennington costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Bennington?
January, March and November are great times to search for cheap Bennington vacation packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and hotels.
How many days is enough for Bennington?
To get the most out of your Bennington vacation, we suggest staying for 2 days. Divide your time between visiting Bennington Centre for the Arts, Old First Congregational Church and other leading sights, as well as experiencing neighbourhoods like Old Bennington and South Shaftsbury. If you've got some spare time, include a day trip in your Bennington vacation itinerary.
Is it worth booking a vacation package to Bennington?
Bennington has everything you need for an amazing escape. Get your Bennington vacation off to a flying start by checking out major attractions like Bennington Battle Monument.
How to find the best Bennington package deals?
Use Expedia's filters to help you find some great Bennington package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Bennington package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Bennington vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can customize your Bennington escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Bennington?
If you're considering a spontaneous Bennington adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Bennington?
- Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Bennington.
- Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will likely be the biggest expense during your trip to Bennington.
- Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Bennington. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose a 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.
