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.
Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

2.5 out of 5
per person
Oct 17 - Oct 19
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,008 reviews)
Great location and nice amenities including great breakfast!

Reviewed on Jul. 30, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Oct 17 - Oct 19
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.8/10 Good! (1,174 reviews)
The bathroom smells so bad, looks clean but smells like mold

Reviewed on Jul. 30, 2025

La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
per person
Oct 17 - Oct 19
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (1,000 reviews)
Breakfast was disappointing, bed was comfortable

Reviewed on Jul. 28, 2025

Homewood Suites By Hilton Schenectady

Homewood Suites By Hilton Schenectady

3 out of 5
per person
Oct 17 - Oct 19
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
The reception desk personnel were helpful and very friendly. We enjoyed the pool. Breakfast delighted my grandson. The breakfast assistants were kind to him. We enjoyed the suite and the amenities.

Reviewed on Jul. 26, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Oct 17 - Oct 19
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
Prixw reasonable with good service

Reviewed on Jul. 31, 2025

Ready to book your vacation to Bennington?

 

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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 $145 per night from Aug 31 to Sep 1
CA $145
CA $158 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
"Such a lovely hotel in a sweet town!"

Reviewed on Jul. 28, 2025

Hotel Vervana, Trademark Collection by Wyndham
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 $222 per night from Aug 17 to Aug 18
CA $222
CA $242 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"I thought i booked a king suite with a sleeper couch and come to find out it was only a king bed. Guess the description was wrong."

Reviewed on Jul. 17, 2025

Hampton Inn Bennington
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Aug 7 to Aug 8
CA $159
CA $174 total
Aug 7 - Aug 8
includes taxes & fees
7.6/10 Good! (866 reviews)
"Great customer service. Perfect spot for a berkshires getaway"

Reviewed on Jul. 20, 2025

Best Western Bennington
See all 741 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
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What to do in Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

CA $23
per traveller
Vermont RT 100 Self 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 $918 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.