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.
The Whitlock
CA $811
per person
Nov 30 - Dec 4
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
8.4/10 Very good! (385 reviews)
The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property.
Reviewed on Sep 25, 2026
Hideaway Inn Lenox
CA $866
per person
Nov 30 - Dec 4
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
7.8/10 Good! (60 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.
Reviewed on Sep 18, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
CA $703
per person
Nov 30 - Dec 4
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (989 reviews)
Very nice property excellent to stay with family. Especially if you have little ones with you. Property was clean well maintained. Helpful professional staff.
Reviewed on Sep 28, 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 6 - Oct 7
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"X"
Reviewed on Sep 27, 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
CA $194
CA $211 total
Sep 29 - Sep 30
includes taxes & fees
8.2/10 Very good! (171 reviews)
"This is a old motel. The room had a sweet overpowering odor of room deodorizer with a musty smell behind it. The towels had stains on them. Also, their description says they offer a breakfast. Their idea of a breakfast is a bottle of apple or orange juice, a granola bar, and a mandarin orange fruit ..."
Reviewed on Sep 27, 2026
Bennington Motor Inn
143 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
CA $106
CA $116 total
Sep 29 - Sep 30
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 $675 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.
