Bennington Vacation Packages
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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.
Albany Airport Inn
CA $712
per person
Oct 16 - Oct 19
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
6.6/10 (1,005 reviews)
Great staff! Checked in and returned my rental car. I called the hotel after dropping off the car and they sent the shuttle to pick me up within minutes and dropped me off at the door number closest to my room. Room can be updated a little bit.. not by much though.
Reviewed on Aug 12, 2026
Hampton Inn & Suites Albany-Downtown
Downtown Albany
CA $874
per person
Oct 16 - Oct 19
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
8.8/10 Excellent! (1,058 reviews)
The hotel was very busy and only one elevator worked. There were stains on the mattress pad visible under the thin sheets. The breakfast was minimal. The parking situation was not explained well ($20/night) Place has potential to be much better
Reviewed on Aug 9, 2026
Hilton Albany
Downtown Albany
CA $861
per person
Oct 16 - Oct 19
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
7.4/10 Good! (1,154 reviews)
It’s in a good location. Staff at front desk are rigid & unfriendly. AC did not work throughout an entire weekend long dance completion event. Mouse ran through the women’s Hair/Make-up room. Bathtub in room didn’t drain when shower was used. Nice restaurant & bar staff and food was fairly good. I would not stay again.
Reviewed on Aug 12, 2026
Fairfield Inn & Suites by Marriott Albany Downtown
Downtown Albany
CA $939
per person
Oct 16 - Oct 19
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
8.6/10 Excellent! (1,002 reviews)
The room was ok, pretty basic, but the A/C did not work - it was 78° in the room, and the bathroom sink drain was stopped up with hair that had never been cleaned. The staff was friendly enough and the breakfast was about what you would expect.
Reviewed on Aug 10, 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 $138
CA $150 total
Aug 30 - Aug 31
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 Aug 11, 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
CA $152
CA $165 total
Aug 13 - Aug 14
includes taxes & fees
8.6/10 Excellent! (132 reviews)
"Staff was very nice and helpful. Rooms were nice but dated. Really not a bad place to stay. The only complaints were that the washing machines were broken so we couldn't do laundry (we're hiking the AT/Long Trail and very dirty clothes) and the breakfast was disappointing (looking forward to a hot ..."
Reviewed on Aug 10, 2026
New Englander Inn Bennington
220 Northside Drive Bennington VT
Fully refundableReserve now, pay when you stay
CA $151
CA $164 total
Aug 30 - Aug 31
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 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.
Hemmings Motor News Car Lover's Convenience Store & Vehicle Display
8.6/10 (18 reviews)
You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display 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.
Woodford State Park
8.8/10 (11 reviews)
You can take time to visit Woodford State Park during your travels to Woodford.
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.
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.
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.
Prospect Mountain Nordic Ski Center
8.6/10 (8 reviews)
Hit the slopes in Woodford with a visit to Prospect Mountain Nordic Ski Center. Discover the area's mountain views and coffeehouses.
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 $712 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.
