Bennington Vacation Rentals

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Bennington Travel Guide Travel Guide

Located in the Southern corner of Vermont, Bennington is a charming small town defined by the lush green mountains surrounding it. The town’s nature has served as inspiration for poets and artists like Robert Frost, Grandma Moses, and Norman Rockwell. Today, inspiration still awaits at this Northeastern getaway destination.

Things to Do in Bennington Travel Guide

Top things to do include visiting the top of the Bennington Battle Monument, which is the tallest structure in Vermont, attending a Sunday service at Vermont’s first Protestant Church, the Old First Church, and touring the Park-McCullough historic Victorian home in North Bennington. For hiking, climb up the summit of the Appalachian Trail to witness a stunning view of Bennington, and visit Stratton Mountain in the winter months for world class skiing.

Best Places to Stay in Bennington Travel Guide

Your best bet for lodging in Bennington is a classic bed and breakfast that demonstrates New England hospitality. The Eddington House Inn is a B&B gem, named a 2014 Yankee Editor’s Pick for “Best Small B&B.” For a more spacious suite with pasture views, Taraden Bed & Breakfast is the way to go. Elsewhere, set on an 18th-century property, the now restored Four Chimneys Inn would be your ideal choice for a stay that brings you back in time.

Best Time to Visit Bennington Travel Guide

Bennington is a 4 season town with activities for all of the Seasons. The warmest time of year is early to mid-July where highs are regularly around 83 degrees, perfect for a round of golf. Meanwhile, the winter months are snowy enough for world class skiing.

Food in Bennington Travel Guide

For a classic American experience, grab a seat at Madison Brewing Company Pub & Restaurant, a two-level pub with 14 of its own brews on tap, and a menu that features sandwiches and burgers, as well as steak, meatloaf, salads and pasta. For some satisfying breakfast, visit Jensen's Restaurant, a comfort food diner located on North Street. And for a fancy dinner, eat at Fuji Hibachi, Sushi and Asian Bistro, a small restaurant known for having good sushi and even better service.

Price and Availability in Bennington

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The cheapest day to stay at a vacation rental in Bennington tends to be Tuesday, while the most expensive day tends to be Sunday. Vacation homes in Bennington tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Bennington is in June, while the cheapest month is in November. The most popular time to book a vacation rental in Bennington is in the high season in July. Bennington has its low season in May, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Bennington

Rainy days
88° 25°
91° 32°
92° 55°
89° 43°
84° 28°
77° 17°
75° 14°
64° -9°
66° -6°
58° -9°
64° 24°
Rainy days

This climate histogram shows you the weather patterns in Bennington. The warmest months in Bennington are June and July, when temperatures reach 92 ˚F. The coolest month is January, when temperatures drop to -9 ˚F. The wettest month in Bennington is June with 4.58 inches of rain, while the driest month is December with 1.34 inches of rain.

What Expert Travelers Think

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    Sarah PoolTammymum
  • — makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

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Vacation Rentals in Bennington

Pick the perfect rental for your trip at We compare Airbnb, Priceline, Agoda and others. We have 199 vacation rentals, hotels and other places to stay in Bennington ranging from budget options to luxury places to stay. If you are trying to save money, the cheapest place to stay in Bennington is only $38 per night. An average accommodation in Bennington costs on average $131 per night.

Those looking to get some work finished during their trip to Bennington can pick from 87 places to stay that include WiFi. We have 14 accommodations that include a breakfast included. Fitness addicts can get a workout in during their stay by choosing from 6 accommodations that have gyms. If you are driving to Bennington, you'll want to pick from 89 places to stay that provide parking. 11 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then be sure to select one of the 32 pet-friendly accommodations available.

125 of the accommodations in Bennington have been rated by previous guests. They rated 70% as excellent or good. 62 places to stay in are instantly bookable.

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