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.
Tru By Hilton Albany Airport, NY

Tru By Hilton Albany Airport, NY

2.5 out of 5
Price was CA $1,203, price is now CA $1,162 per person
CA $1,162
per person
Dec 21 - Dec 24
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
9/10 Wonderful! (1,960 reviews)

Marriott Albany

Marriott Albany

3.5 out of 5
Price was CA $1,299, price is now CA $1,203 per person
CA $1,203
per person
Dec 21 - Dec 24
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
8.4/10 Very good! (1,001 reviews)
staff at reception is not that polite

Reviewed on Oct 31, 2026

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was CA $1,419, price is now CA $1,357 per person
CA $1,357
per person
Dec 21 - Dec 24
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was CA $1,241, price is now CA $1,199 per person
CA $1,199
per person
Dec 21 - Dec 24
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
We had a 3 night/4 day stay and our room was never cleaned/made up the entire time. I also do not appreciate that breakfast is shut down at 9 am… this does not work for many people. It should be available until AT LEAST 10 am. The parking lot is being worked on and is a bit of a mess.

Reviewed on Oct 30, 2026

The Stockade Inn

The Stockade Inn

2 out of 5
Stockade Historic District
Price was CA $1,384, price is now CA $1,338 per person
CA $1,338
per person
Dec 21 - Dec 24
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Albany (ALB)
9.4/10 Exceptional! (222 reviews)
PERFECT location should the Historic District be of interest...Recommend Solana Bagel & Coffee Shop within the premises...Arthur's Market on Ferry St., Stella's Pasta Bar and Bistro on Union St... Pleasant and responsive staff...Recommend...

Reviewed on Oct 31, 2026

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Bennington Hotel Deals

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Nov 16 to Nov 17
CA $135
CA $148 total
Nov 16 - Nov 17
includes taxes & fees
8.2/10 Very good! (1,005 reviews)
":)"

Reviewed on Oct 31, 2026

Hotel Vervana, Trademark Collection by Wyndham
New Englander Inn Bennington

New Englander Inn Bennington

2.5 out of 5
220 Northside Drive Bennington VT
The price is CA $128 per night from Nov 3 to Nov 4
CA $128
CA $140 total
Nov 3 - Nov 4
includes taxes & fees
New Englander Inn Bennington
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Nov 8 to Nov 9
CA $217
CA $236 total
Nov 8 - Nov 9
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Breakfast had cooked oatmeal And had 3 main items for breakfast each day"

Reviewed on Oct 25, 2026

Hampton Inn Bennington
See all 813 properties in Bennington
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

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.
See properties

What to do in Bennington

Vermont RT 100 App-Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
80% of travellers recommend
Vermont RT 100 App-Guided Driving Audio Tour
See all activities in Bennington

Frequently asked questions

How much does a Bennington vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,162 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.