Bennington Vacations from $306

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Your Bennington Vacation

With a vacation package to Bennington, say goodbye to endless planning and hello to an effortless adventure. Every detail of your escape has been taken care of before departing, so you can enjoy each moment experiencing this interesting city. Every trip to Bennington needs a well-designed itinerary. Fill yours with big-name attractions like Crotched Mountain Ski and Ride Area, Peterborough Players and Greenfield State Park. Stop dreaming and start traveling. Check out the multitude of options on Expedia today and put your Bennington vacation plans into action!

The Latest Bennington vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunset Hill House
The Centennial
Omni Bretton Arms Inn at Mount Washington
Mountain View Grand Resort & Spa
Presidential Mountain Resort
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Bennington Hotel Deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $130 total per night from Jan 12 to Jan 13
$130 total
Jan 12 - Jan 13
Total with taxes and fees
8.4/10 Very Good! (976 reviews)
Nice clean room, very good shower, friendly staff

Reviewed on Jan 3, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 out of 5
80 Concord Street Peterborough NH
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $194 total per night from Jan 15 to Jan 16
$194 total
Jan 15 - Jan 16
Total with taxes and fees
9.2/10 Wonderful! (439 reviews)
Beds were sooo comfortable

Reviewed on Jan 5, 2026

Riverhouse by Weekender (Formerly Jack Daniels Inn)
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St Keene NH
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $195 total per night from Jan 18 to Jan 19
$195 total
Jan 18 - Jan 19
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
The room and property in general was amazing. Super comfortable beds, and room plan. Very walkable to many restaurants and attractions in the town center. Easy parking. I wasnt impressed with the "Bistro" that is essentially a starbucks. Also, no free lounge coffee, you have to buy at the Bistro/starbucks. ...

Reviewed on Dec 28, 2025

Courtyard by Marriott Keene Downtown
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 near Bennington

Bennington, New Hampshire, is an excellent destination for ski enthusiasts and adventure seekers. Visitors can enjoy a range of outdoor activities, including skiing at local resorts, exploring beautiful landscapes, and engaging in various recreational options. With opportunities for vacation sightseeing and day trips, Bennington offers a perfect blend of thrilling adventures and serene nature experiences for all types of travelers.

Shopping

For a unique shopping experience in Bennington, visit StoneFalls Gardens, located 14 miles away, offering charming local goods. If you're up for a drive, the Merrimack Premium Outlets, 24 miles away, features a wide range of brand-name outlets perfect for gift shopping.

Recreation

Experience the charm of Peterborough Players, a vibrant theater just 6 miles from Bennington, offering captivating performances perfect for families. For outdoor enthusiasts, enjoy a round at Shattuck Golf Course or Stonebridge Golf Course, both providing stunning landscapes and invigorating sports activities within 14 and 15 miles, respectively.

Adventure

Experience thrilling skiing at Crotched Mountain Ski and Ride Area, located 2 miles from Bennington, where you can enjoy exciting slopes and a vibrant sports atmosphere. For hiking enthusiasts, the Nashua River Rail Trail, 29 miles away, offers breathtaking scenery and outdoor adventures. Additionally, Pats Peak, 13 miles from Bennington, provides fantastic ski options.

Nightlife

In Bennington, New Hampshire, enjoy a relaxed nightlife at local pubs and bars, such as The Bennington Station and The Olde Bennington Inn. Experience live music, cozy atmospheres, and friendly conversations, perfect for unwinding after a day of exploring this charming New England town.

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

Find the best attractions near Bennington

Bennington, New Hampshire, is perfect for adventure seekers with its skiing, sports, and outdoor activities. Explore the area's natural beauty at local nature reserves and lakes, and visit notable attractions like the Bennington Monument, Bennington Museum, and the historic Battle of Bennington. Don't miss the vibrant local theater scene for an enriching experience. Whether you're seeking eco-friendly adventures or cultural insights, Bennington has something for every traveler.

  • Eaton's Magic Morsel: Experience the charm of this delightful attraction, located 8 miles from Bennington, where sunny vibes create a perfect atmosphere for enjoying sweet treats and local flavors. Visitors can indulge in unique confections and enjoy the warm, inviting ambiance.
  • Franklin Pierce Homestead: Step back in time at this historic house, also 8 miles away from Bennington. Embrace the rich cultural heritage of the 14th president of the United States, exploring the beautifully preserved home and gardens, which reflect the essence of mid-19th century life.
  • Pack Monadnock Mountain: Located 10 miles from Bennington, this mountain offers breathtaking scenery and outdoor adventure. Hike the trails to enjoy panoramic views and connect with nature, making it a perfect escape for outdoor enthusiasts and those seeking stunning landscapes.

Best time to go to Bennington

The best time to visit Bennington is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately high and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.4°F (-5.9°C)Light RainMostly CloudyModerately HighSlightly Low
February23.2°F (-4.9°C)Light RainMostly CloudyModerately HighAverage
March30.7°F (-0.7°C)Light RainMostly CloudyAverageSlightly Low
April42.6°F (5.9°C)Light RainMostly CloudyModerately LowAverage
May55.0°F (12.8°C)Light RainMostly SunnyModerately LowAverage
June63.1°F (17.3°C)Light RainMostly SunnyAverageSlightly High
July69.4°F (20.8°C)Light RainMostly SunnyModerately HighSlightly High
August67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
September60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
October48.9°F (9.4°C)Light RainMostly SunnyModerately LowSlightly High
November36.9°F (2.7°C)Light RainMostly SunnyAverageAverage
December28.0°F (-2.2°C)Light RainMostly CloudyAverageSlightly Low

Tips to save on your trip to Bennington

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Bennington.
  • Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Bennington.
  • 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
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
380
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Crotched Mountain Ski and Ride Area, Peterborough Players and Greenfield State Park

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Frequently asked questions

How much does a Bennington vacation package cost?
You can grab a vacation package to this top destination from $306 on Expedia. But how much your vacation to Bennington costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Bennington?
You can generally find lower prices and better availability in October, November and December. Browse our cheap Bennington vacation packages and you could land some great off-season discounts.
How many days is enough for Bennington?
Typically, a handful of days is enough to explore the top sights during your Bennington vacation. But if you want to have time to unwind or take day trips, think about extending your itinerary.
How to find the best Bennington package deals?
Use Expedia's filters to help you find some tempting Bennington package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Bennington package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Bennington vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Bennington vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Bennington?
If you're planning a spontaneous Bennington trip, 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 score amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Bennington vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Bennington vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

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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.