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 Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $890, price is now CA $717 per person
CA $717
per person
Oct 12 - Oct 16
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,015 reviews)
Staff was great!!

Reviewed on Jul 25, 2026

The Whitlock

The Whitlock

2 out of 5
Price was CA $1,334, price is now CA $1,022 per person
CA $1,022
per person
Oct 12 - Oct 16
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very good! (332 reviews)
Very nice coffee set up in the morning. Staff was super courteous and helpful. Most of property is updated although carpeting and rugs are tired. Location is great, very convenient to Tanglewood and restaurants. Parking is onsite and more than ample. B

Reviewed on Jul 25, 2026

Gedney Farm

Gedney Farm

3.5 out of 5
Price was CA $1,312, price is now CA $1,014 per person
CA $1,014
per person
Oct 12 - Oct 16
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (138 reviews)
Pet friendly and amazing grounds

Reviewed on Jul 17, 2026

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $911, price is now CA $725 per person
CA $725
per person
Oct 12 - Oct 16
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
8.8/10 Excellent! (2,463 reviews)

Berkshires Untold

Berkshires Untold

3.5 out of 5
Price was CA $1,113, price is now CA $917 per person
CA $917
per person
Oct 12 - Oct 16
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,018 reviews)
Nice room, nice bar, fire pit. Don’t eat dinner there.

Reviewed on Jul 25, 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 $152 per night from Aug 3 to Aug 4
CA $152
CA $166 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very good! (1,009 reviews)
"Upon entering the stairwell, there was a terrible smell that reminded me of a house full of animals that has never been cleaned/aired out. The bathroom in our designated room had a dirty shower floor, dust covering everything and dirt/grime/mold in the tile grout. The bed was squeaky, the mattress ..."

Reviewed on Jul 26, 2026

Hotel Vervana, Trademark Collection by Wyndham
Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 6 to Aug 7
CA $154
CA $167 total
Aug 6 - Aug 7
includes taxes & fees
Knotty Pine
New Englander Inn Bennington

New Englander Inn Bennington

2.5 out of 5
220 Northside Drive Bennington VT
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Aug 18 to Aug 19
CA $168
CA $183 total
Aug 18 - Aug 19
includes taxes & fees
7.6/10 Good! (977 reviews)
"The room was very clean. Beds comfortable but bed frame was metal and made loud noise sometimes while on the bed. Staff was great. Pool closed and ice machine broken. Breakfast was good. Picnic table area was dirty from smokers who didn't bother to use the 2 ash trays there."

Reviewed on Jul 21, 2026

New Englander Inn Bennington
See all 810 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.
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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 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

CA $24
per traveller
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 $717 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.