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.
The Manchester View
CA $1,152
per person
Oct 30 - Nov 1
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
9.4/10 Exceptional! (902 reviews)
Property has been renovated-it is very clean and modern. Nice simple breakfast served. Housekeeping didn’t show the 2nd day of our stay. ( we hunted them down for towels before getting ready for a wedding. They offered to come then- but it was too late in the day)
Great views and quite location.
Reviewed on Sep 25, 2026
Brook Bound Inn
CA $1,297
per person
Oct 30 - Nov 1
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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
The Equinox Golf Resort And Spa
Manchester Village Historic District
CA $1,352
per person
Oct 30 - Nov 1
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
7.4/10 Good! (665 reviews)
Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better.
Reviewed on Sep 23, 2026
Knotty Pine
CA $1,351
per person
Oct 30 - Nov 1
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Albany (ALB)
8.4/10 Very good! (154 reviews)
The woman who checked us in was wonderful. However, the rooms were listed as having two queen beds. They were full size beds and way to small for four people in the room. Sheet was stained, pleather chair was flaking and wall lights were all crooked.
Reviewed on Sep 26, 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 $150
CA $164 total
Oct 5 - Oct 6
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"I travel for work and had the opportunity to stay at this property for 2 months. This is a great lodge in a lovely part of the country. The friendly staff will go out of their way to accomodate guests if at all possible. This is a modernized lodge type property in a picturesque setting. There are ..."
Reviewed on Sep 22, 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
CA $194
CA $211 total
Sep 28 - Sep 29
includes taxes & fees
8.2/10 Very good! (169 reviews)
"The woman who checked us in was wonderful. However, the rooms were listed as having two queen beds. They were full size beds and way to small for four people in the room. Sheet was stained, pleather chair was flaking and wall lights were all crooked."
Reviewed on Sep 26, 2026
Bennington Motor Inn
143 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
CA $133
CA $145 total
Sep 28 - Sep 29
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.
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.
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.
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 $1,152 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.
