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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 Wiltwyck
The Equinox Golf Resort & Spa
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Luxury Private Estate w Pool Near Rhinebeck
Lodges At Cresthaven
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Discover the most popular places to visit in Bennington

What to do in Bennington

Bennington Hotel Deals

Knotty Pine

Knotty Pine

2.5 out of 5
130 Northside Dr Bennington VT
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $165 total per night from Jan 18 to Jan 19
$165 total
Jan 18 - Jan 19
Total with taxes and fees
8.6/10 Excellent! (54 reviews)
Pet friendly, cooking was great plus, warm room

Reviewed on Jan 5, 2026

Knotty Pine
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square Bennington VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $142 total per night from Feb 1 to Feb 2
$142 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Good Beautiful stay

Reviewed on Jan 10, 2026

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
$106 nightly
The price is $115 total per night from Jan 25 to Jan 26
$115 total
Jan 25 - Jan 26
Total with taxes and fees
7.6/10 Good! (949 reviews)
Location and amenities basic, which is all we needed.

Reviewed on Jan 12, 2026

Best Western 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 $292 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.

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