Bennington Vacations from $418

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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.

The Sunny G B&B

$418

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Manchester (MHT)

9.4/10 Exceptional! (711 reviews)

Stonybrook Motel & Lodge

$554

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Manchester (MHT)

7.6/10 Good! (1,008 reviews)

The Village of Loon Mountain Fixed Rooms

Save 100% on your flight

$892

per person

Dec 26 - Dec 30

found 23 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Manchester (MHT)

8.6/10 Excellent! (67 reviews)

Presidential Mountain Resort

$848

per person

Dec 26 - Dec 30

found 24 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Manchester (MHT)

9.6/10 Exceptional! (304 reviews)

Attitash Mountain Village

$840

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Manchester (MHT)

8.6/10 Excellent! (578 reviews)

It was not like the picture s. Its basically a 1 room condo with a pull down bed and a Castro convertible couch. It smelled musty initially but aired out quickly. I feel it was portrayed as a hotel but its not. There was no sign and the check in desk took some driving and asking people where it was.

Reviewed on Oct 7, 2026

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Bennington Hotel Deals

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Bennington NH

$367 nightly

$398 total

Oct 18 - Oct 19

Total with taxes and fees

10/10 Exceptional! (16 reviews)

"It was exactly as described and very private. We had a couple issues but communication was good and everything was sorted out."

Reviewed on Oct 1, 2026

Best Western Plus Keene Hotel

401 Winchester St Keene NH

Fully refundableReserve now, pay when you stay

$142 nightly

$154 total

Nov 1 - Nov 2

Total with taxes and fees

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

Fully refundableReserve now, pay when you stay

$119 nightly

$129 total

Nov 2 - Nov 3

Total with taxes and fees

See all 333 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 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	21.4°F (-5.9°C)	Light Rain	Mostly Cloudy	Moderately High	Slightly Low
February	23.2°F (-4.9°C)	Light Rain	Mostly Cloudy	Moderately High	Average
March	30.7°F (-0.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	42.6°F (5.9°C)	Light Rain	Mostly Cloudy	Moderately Low	Average
May	55.0°F (12.8°C)	Light Rain	Mostly Sunny	Moderately Low	Average
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Average	Average
September	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Average	Average
October	48.9°F (9.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly High
November	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Average
December	28.0°F (-2.2°C)	Light Rain	Mostly Cloudy	Average	Slightly 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

What's included in a Bennington vacation package?

A Bennington vacation package lets you combine round-trip flights, a hotel stay, and a rental car, offering convenience for exploring this outdoor and nature destination. Around 1 in 10 hotels in the area offers airport shuttle service, which can be helpful for transfers from Boston, MA (BOS-Logan Intl.). Additionally, about half of hotels include free breakfast, providing a convenient start to your day before heading out to the ski slopes or hiking trails.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Bennington vacation package?

When you bundle, you can save up to 30%*. To save money on a Bennington package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What are the top things to do in Bennington?

Bennington, United States of America, is an outdoor and nature destination, offering a range of activities for your Bennington vacation:Browse and book things to do in Bennington on Expedia.

Do you need to rent a car in Bennington, or is public transport enough?

For a Bennington vacation package, renting a car is highly recommended to fully explore this outdoor and nature destination. Bennington is primarily known for skiing and other outdoor activities, with many attractions spread out from the central area. A car offers the flexibility to reach ski resorts like Crotched Mountain Ski and Ride Area, about 4 miles away, or natural areas such as Pack Monadnock Mountain, about 6 miles from central Bennington. This allows travelers to easily access various trailheads, golf courses like Crotched Mountain Golf Club, and scenic spots at their own pace. For Bennington vacation packages with flights, a rental car allows you to make the most of the region's outdoor offerings.

Can I change or cancel my Bennington vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Bennington vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Bennington vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Bennington vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Bennington?

To find last-minute vacation packages to Bennington, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Bennington vacation packages?

Free cancellation on a Bennington vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Bennington vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Bennington getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Bennington vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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Hancock Vacation Rentals

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

Bennington Vacations from $418

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Bennington Vacation

The Latest Bennington vacation packages

The Sunny G B&B

Stonybrook Motel & Lodge

The Village of Loon Mountain Fixed Rooms

Presidential Mountain Resort

Attitash Mountain Village

Bennington Hotel Deals

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Best Western Plus Keene Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

Find the Best Bennington Vacation Packages

Things to do near Bennington

Find the best attractions near Bennington

Best time to go to Bennington

Tips to save on your trip to Bennington

Bennington Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

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