Bennington Vacations from $366

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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.
The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Save 100% on your flight
Price was $535, price is now $366 per person
$366
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.4/10 Very Good! (1,014 reviews)
Very nice staff great room a lot to do around

Reviewed on Oct 5, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,453, price is now $910 per person
$910
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
7.4/10 Good! (529 reviews)
Outdoor hot tub was pleasant, but the property looks and feels old and worn. Front desk staff were not particularly pleasant or helpful. Restaurants service was quite slow.

Reviewed on Oct 4, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $633, price is now $462 per person
$462
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,006 reviews)
Clean room. Great service. We got an upgrade with a view over the river.

Reviewed on Oct 8, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Save 100% on your flight
Price was $634, price is now $477 per person
$477
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8/10 Very Good! (1,148 reviews)
The staff was excellent. The items in their ministore were a little less diverse than other locations. The dining facilities were poor - no continental breakfast option. The rooms were nice and clean and the area was very quiet.

Reviewed on Oct 8, 2025

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
Price was $498, price is now $385 per person
$385
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (1,186 reviews)
I was very comfortable

Reviewed on Oct 5, 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

Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (924 reviews)
"The staff was great. The refrigerator in my room wasn’t working. I went to the front desk and the girl was unable to reach maintenance, but she managed to find a new fridge, carried it to my room and set it up. She went above and beyond and I was truly thankful. Also, I was pleasantly surprised to ..."

Reviewed on Oct 6, 2025

Best Western Bennington
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $82 total per night from Oct 27 to Oct 28
$82 total
Oct 27 - Oct 28
Total with taxes and fees
7.4/10 Good! (621 reviews)
"Very clean"

Reviewed on Oct 5, 2025

The Autumn Inn
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
$108 nightly
The price is $118 total per night from Nov 2 to Nov 3
$118 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (999 reviews)
"Friendly staff easy check in accessible to different places"

Reviewed on Sep 24, 2025

Hotel Vervana, Trademark Collection by Wyndham
See all 785 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.

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 $366 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.