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.

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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 $155 per night from Aug 4 to Aug 5
CA $155
CA $169 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (999 reviews)
"Newly renovated. Quiet area. Very close to Bennington museum and monument ."

Reviewed on Jul. 6, 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 $220 per night from Jul 20 to Jul 21
CA $220
CA $240 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (998 reviews)
"It was all we expected."

Reviewed on Jul. 7, 2025

Hampton Inn Bennington
The Autumn Inn
The Autumn Inn
2 out of 5
924 East Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 14 to Jul 15
CA $122
CA $133 total
Jul 14 - Jul 15
includes taxes & fees
7.6/10 Good! (580 reviews)
"Staff was very helpful and very knowledgeable very nice people very clean."

Reviewed on Jul. 6, 2025

The Autumn Inn
See all 738 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

Family Vacations

Family Vacations

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 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.