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.
Berkshire Inn
CA $868
per person
Oct 15 - Oct 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
7.8/10 Good! (914 reviews)
Conveniently located to Tanglewood and Jacob's pillow and other attractions in towns in western Mass. All brand new decorated room. Neighborhood is a little down market but safe and quiet at night. Good value for money.
Reviewed on Aug 27, 2026
Quality Inn Great Barrington
CA $928
per person
Oct 15 - Oct 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.6/10 Excellent! (1,025 reviews)
It is a good value for money. Location is very good, right on the main street, just one block away from downtown Great Barrington with almost all the restaurants and shops within walking distance. Downside is that it is a motel, not a standard hotel. If you have a room on the second floor then you have to haul your luggage up as there is no elevator. Breakfast has bare minimum items. It would help if fresh fruit and cereal is added. There is improvement possible in the overall upkeep. However, I'll certainly recommend it for a short stay for budget customers like me.
Reviewed on Sep 1, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
CA $1,299
per person
Oct 15 - Oct 20
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Albany (ALB)
8.8/10 Excellent! (808 reviews)
This facility appeared to be brand new. Breakfast was excellent and the dining area was spacious and attractive. We would definitely recommend this hotel and will stay here again when we are back in the area!
Reviewed on Aug 30, 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 $149 total
Sep 13 - Sep 14
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"Nice staff. Dirty pool. Rooms were okay."
Reviewed on Aug 27, 2026
Knotty Pine
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
CA $161
CA $176 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very good! (154 reviews)
"Clean and convenient."
Reviewed on Aug 31, 2026
Bennington Motor Inn
143 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
CA $115
CA $125 total
Sep 3 - Sep 4
includes taxes & fees
7.6/10 Good! (490 reviews)
"I would rather not enumerate the many failings of this business."
Reviewed on Aug 28, 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.
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.
Woodford State Park
8.8/10 (11 reviews)
You can take time to visit Woodford State Park during your travels to Woodford.
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 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.
Harmon Hill
8.0/10 (6 reviews)
Commune with nature and explore the great outdoors at Harmon Hill during your travels in Woodford. While you're here, you can savor the charming 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 $868 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.
