Bennington Vacations from $319

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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.

The Latest Bennington vacation packages

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 12 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
8.6/10 Excellent! (1,862 reviews)
Wonderful property in an idyllic setting! Everything you need for a quality vacation with friends or family. One of the most relaxing getaways I've ever had.

Reviewed on Jul 11, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 25
found 17 hours ago
Roundtrip non-stop flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (463 reviews)
Wonderful trip and wonderful resort!

Reviewed on Jul 1, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Cornell Inn was lovely. The place is so clean- and I’m a germaphobe! The staff was kind, helpful and welcoming. The breakfast was delicious and served outside in a beautiful garden. Would definitely recommend.

Reviewed on Jul 7, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
7.4/10 Good! (486 reviews)
Just love the very historic sence

Reviewed on Jul 6, 2025

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 20
found 12 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Great service and a wonderful place to stay

Reviewed on Jul 9, 2025

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Discover the most popular places to visit in Bennington

Bennington Battle Monument showing landscape views

Bennington Battle Monument

4.5/5(71 reviews)

Learn about the local history of Old Bennington when you spend time at Bennington Battle Monument. In the area, take in the art scene and mountain views.

Bennington Battle Monument
2017

Old First Congregational Church

5/5(4 reviews)

Find out about the history of Old Bennington with a stop at Old First Congregational Church. In the area, take in the art scene and mountain views.

Old First Congregational Church

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

4.5/5(2 reviews)

You can spend an afternoon browsing the exhibits at Hemmings Motor News Car Lover's Convenience Store & Vehicle Display in Bennington. While you're here, you can savor the charming coffeehouses.

Hemmings Motor News Car Lover's Convenience Store & Vehicle Display

What to do in Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

$17
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Bennington

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
$113 nightly
The price is $123 total per night from Aug 4 to Aug 5
$123 total
Aug 4 - Aug 5
Total includes taxes and 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
$161 nightly
The price is $175 total per night from Jul 20 to Jul 21
$175 total
Jul 20 - Jul 21
Total includes taxes and 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
$89 nightly
The price is $97 total per night from Jul 14 to Jul 15
$97 total
Jul 14 - Jul 15
Total includes taxes and fees
7.6/10 Good! (581 reviews)
"Staff was very helpful and very knowledgeable very nice people very clean."

Reviewed on Jul 6, 2025

The Autumn Inn
See all 747 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.

Find the Best Bennington Vacation Packages

Bennington Essential Information

Language
English
Currency
U.S dollars
Population
9,100
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Lake Shaftsbury State Park, Prospect Mountain Cross-Country Ski Center and Woodford State Park

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Frequently asked questions

How much does a Bennington vacation package cost?
Offering excellent value package deals from $319 on Expedia, you'll be thrilled with how little a vacation to Bennington costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bennington?
You can typically find lower prices and greater availability in September, October and November. Take a look at our cheap Bennington vacation packages and you could score some great off-season discounts.
How many days is enough for Bennington?
We recommend booking a Bennington vacation for at least 2 days. This will give you plenty of time to tick off key attractions including Robert Frost Stone House Museum and Southern Vermont College, as well as explore neighborhoods like Old Bennington and South Shaftsbury. You might even be able to slot in a day trip beyond Bennington.
Is it worth booking a vacation package to Bennington?
It's no wonder a Bennington vacation is on the must-do list of many travelers. Leading attractions like Bennington Battle Monument are just the start of what you can explore here.
How to find the best Bennington package deals?
Finding a cheap Bennington package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bennington vacation as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Bennington?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Bennington adventure.
How to plan a trip to Bennington?

  1. Choose when to get away: Check your calendar and pack your bags. Your favorite season and the available activities will also help you decide when to vacation in Bennington.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to save for your trip to Bennington. Then, pick a hotel that matches your budget, whether that's a wallet-friendly option or a swankier retreat.
  3. Discover Bennington using Expedia's trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Bennington. You can also save your favorite places, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Bennington, you can figure out the ideal length of your break. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  5. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Bennington vacation package.
  6. Book any activities or day trips: Now to the fun part --- locking in everything you want to do and see. Browse some of the top things to do in Bennington and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Bennington vacation packages?
Secure your dream escape to Bennington with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck --- we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.