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
90° 49°
87° 43°
84° 33°
78° 28°
73° 10°
57° -4°
56° -12°
63° -8°
76° 19°
83° 33°
86° 36°
Rainy days

This climate histogram shows you the weather patterns in Bennington. The hottest month in Bennington is June, when temperatures peak at 90 ˚F. The coolest month is December, when temperatures drop to -12 ˚F. The wettest month in Bennington is March with 5.92 inches of rain, while the driest month is October with 1.41 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Bennington

Find the perfect rental for your trip at We aggregate Airbnb, Priceline, Agoda and others. AllTheRooms has 199 rentals, hotels and other great places to stay during your time in Bennington, with everything from budget hostels and homestays to extravagant Airbnbs and hotels. When traveling on a budget, the most economical place to stay in Bennington is available at $38 per night. On average, a place to stay in Bennington will cost you $131 per night.

Those needing to get some work done during their trip to Bennington can pick from 87 places to stay that provide WiFi. 14 places to stay include a breakfast. Choose from 6 accommodations that provide gym options, so you don't miss a single workout. Driving to Bennington? Then choose one of the 89 places to stay that comes with a parking spot included. We have 11 vacation rentals that have a pool or jacuzzi.

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

125 of the accommodations in Bennington have been reviewed and rated. 70% are rated excellent or good. 62 places to stay in are instantly bookable.

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