Bennington Vacations from $470

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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.
Hill Farm Inn

Hill Farm Inn

$470
per person
Nov 13 - Nov 15
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.6/10 Exceptional! (179 reviews)
Our favorite place to stay!!

Reviewed on Aug 11, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

Save 100% on your flight
$543
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (1,000 reviews)
Hideaway Inn Lenox

Hideaway Inn Lenox

$560
per person
Nov 6 - Nov 10
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.6/10 Good! (50 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.

Reviewed on Sep 18, 2026

Gedney Farm

Gedney Farm

$563
per person
Nov 4 - Nov 7
found 11 hours ago
Roundtrip flight included
Houston (IAH) to Albany (ALB)
9.4/10 Exceptional! (141 reviews)
Beautiful location with a fantastic chef and meal options. Lee the bartender was great, too!

Reviewed on Sep 15, 2026

Brook Bound Inn

Brook Bound Inn

$879
per person
Nov 25 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!

Reviewed on Aug 30, 2026

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Stay near popular Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
This 306-foot obelisk commemorates a pivotal Revolutionary War battle and stands as Vermont's tallest structure. Ascend to the observatory for breathtaking views spanning Vermont, Massachusetts, and New York.
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Southern Vermont College

8.2/10 (22 reviews)
Explore the historic Everett Mansion on the former Southern Vermont College campus with its striking architecture. Wander the 371-acre grounds for breathtaking views of the Green Mountains in this peaceful setting.
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Prospect Mountain Cross-Country Ski Center

9.0/10 (28 reviews)
Vermont's highest-based Nordic ski center offers over 30 kilometers of groomed trails for all skill levels. Warm up by the stone fireplace in the cozy lodge after conquering the pristine mountain routes.
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Woodford State Park

8.8/10 (11 reviews)
Vermont's highest campground at 2,400 feet, Woodford State Park surrounds pristine Adams Reservoir. Explore the lakeside trail through forests or rent a boat to fish for brook trout in this mountain sanctuary.
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Bennington Museum

9.0/10 (50 reviews)
Home to the world's largest public collection of Grandma Moses paintings, this museum celebrates Vermont's cultural heritage. Explore Revolutionary War artifacts and view the galleries.
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Bennington Center for the Arts

8.6/10 (22 reviews)
This cultural hub showcases diverse art exhibitions, Native American works, and Vermont's heritage through its Covered Bridge Museum. Explore multiple galleries and surrounding gardens for a complete artistic immersion.
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Bennington Potters Yard

8.0/10 (11 reviews)
Watch skilled artisans shape clay into beautiful stoneware at this historic pottery workshop dating back to 1948. Tour the factory floor to witness the crafting process before browsing finished pieces.
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Robert Frost Stone House Museum

9.2/10 (15 reviews)
You can spend an afternoon exploring the galleries in Robert Frost Stone House Museum during your trip to Bennington. Discover the area's charming coffeehouses and its fascinating museums.
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What to do in Bennington

Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 App-Guided Driving Audio Tour

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

Bennington Hotel Deals

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT
$114 nightly
$124 total
Sep 29 - Sep 30
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"I travel for work and had the opportunity to stay at this property for 2 months. This is a great lodge in a lovely part of the country. The friendly staff will go out of their way to accomodate guests if at all possible. This is a modernized lodge type property in a picturesque setting. There are ..."

Reviewed on Sep 22, 2026

Hotel Vervana, Trademark Collection by Wyndham
Knotty Pine

Knotty Pine

130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
$129 nightly
$140 total
Sep 24 - Sep 25
Total with taxes and fees
8.2/10 Very Good! (166 reviews)
"Quaint roadside motel that harkens back to a different time. Clean. Comfortable. Friendly staff. Close to downtown and Bennington Battlefield. Recommended."

Reviewed on Sep 20, 2026

Knotty Pine
Bennington Motor Inn

Bennington Motor Inn

143 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
$89 nightly
$97 total
Sep 24 - Sep 25
Total with taxes and fees
Bennington Motor Inn
See all 811 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

Things to do in and around Bennington

Bennington, Vermont, is an ideal destination for outdoor enthusiasts, offering a range of activities such as skiing at local resorts and exploring scenic ski fields. Visitors can enjoy various recreational options, including vacation sightseeing and outdoor adventures. Whether you’re looking for day trips or thrilling activities, Bennington provides a perfect backdrop for an unforgettable adventure in nature.

Shopping

In Bennington, visit Hemmings Motor News Car Lover's Convenience Store for unique automotive gifts and Bennington Potters Yard for handcrafted pottery. If you're up for a drive, check out Colonial Plaza, 13 miles away, offering a mix of shops and a vibrant family-friendly atmosphere.

Recreation

At Taconic Golf Club, enjoy a round of golf surrounded by the beautiful Vermont landscape, perfect for relaxation and socializing. Visit Windsor Lake Park for serene walks, picnics, and unwinding by the water, offering a tranquil escape to rejuvenate your spirit.

Adventure

Experience the thrill of skiing at Mount Snow, located 16 miles from Bennington, where you can enjoy an exhilarating day on the slopes. For hiking enthusiasts, the Harmon Hills Trail offers stunning scenery and outdoor adventure right in Bennington, making it perfect for nature lovers.

Nightlife

Experience a cozy night in Bennington with a drink at the lively Bennington Station Restaurant & Pub. For a more laid-back vibe, visit the charming The Publyk House, where local brews and good company create a welcoming atmosphere. Enjoy live music and friendly conversation in this quaint Vermont town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Bennington

Bennington, Vermont, offers a fantastic blend of ski, adventure, and outdoor activities, making it an ideal vacation spot. Explore historic sites like the Bennington Battle Monument and the Bennington Museum, or enjoy performances at the local theater. Don't miss the natural beauty of nearby state parks, perfect for family experiences and cultural enrichment. For accommodations, consider hotels near the battle monument for convenient access to these attractions.

  • Bennington College: Nestled 3 miles from Bennington, this historic college offers a vibrant cultural atmosphere with its stunning architecture and beautiful campus. Visitors can explore the rich artistic community and enjoy various events and exhibitions that highlight creativity and innovation.
  • Bennington Battle Monument: Located within Bennington, this impressive monument commemorates a pivotal Revolutionary War battle. Climb to the top for panoramic views of the surrounding landscape and delve into the rich history that shaped the nation.
  • Bennington Museum: Situated in the heart of Bennington, this museum showcases local history, art, and culture. Visitors can explore fascinating exhibits that highlight the region's heritage, including the works of renowned artists and historical artifacts.

Best time to go to Bennington

The best time to visit Bennington can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Bennington falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Bennington falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.2°F (-6.0°C)Light RainMostly CloudyAverageAverage
February23.4°F (-4.8°C)Light RainMostly CloudyAverageSlightly High
March31.5°F (-0.3°C)Light RainMostly CloudyAverageAverage
April43.7°F (6.5°C)Light RainMostly CloudyModerately LowSlightly Low
May56.5°F (13.6°C)Light RainMostly SunnyModerately LowSlightly Low
June63.9°F (17.7°C)Light RainMostly SunnyAverageAverage
July70.0°F (21.1°C)Light RainMostly SunnyModerately HighSlightly High
August68.2°F (20.1°C)Light RainMostly SunnyModerately HighAverage
September61.0°F (16.1°C)Light RainMostly SunnyAverageAverage
October49.3°F (9.6°C)Light RainMostly CloudyModerately HighSlightly High
November36.9°F (2.7°C)Light RainMostly SunnyModerately LowSlightly Low
December28.2°F (-2.1°C)Light RainMostly CloudyAverageAverage

Tips to save on your trip to Bennington

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Bennington during the low season (April to May and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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 $470 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

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