Bennington Vacation Rentals

Check prices for these upcoming dates

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

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
70°
3
64° 24°
3
88° 25°
2
91° 32°
3
92° 55°
5
89° 43°
4
84° 28°
4
77° 17°
4
75° 14°
3
64° -9°
3
66° -6°
1
58° -9°
3
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Rainy days

This climate histogram shows you the weather patterns in Bennington. The hottest month in Bennington is June, when temperatures peak at 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

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels

Vacation Rentals in Bennington

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, Priceline, Agoda and many more. Bennington has 199 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, luxury travelers and everything in between. When traveling on a budget, the most economical place to stay in Bennington is available at $38 per night. An average accommodation in Bennington costs on average $131 a night.

If you want an internet connection during your time in Bennington, then you can choose from over 87 places to stay that have WiFi internet. We have 14 accommodations that include a breakfast included. Choose from 6 places to stay that provide gym options, so you don't miss a single workout. If you are driving to Bennington, you'll want to pick from 89 places to stay that provide parking. We have 11 hotels and vacation rentals that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 32 accommodations that are designated as pet-friendly.

125 of the accommodations in Bennington have been reviewed and rated. 70% are rated great. You can instantly book any of 62 places to stay right now.

Destinations near Bennington

  • Killington3,197 Properties
  • Stowe2,508 Properties
  • Ludlow1,575 Properties
  • Warren982 Properties
  • Dover899 Properties
  • Burlington646 Properties
  • Smugglers Notch467 Properties
  • Wilmington459 Properties
  • Waitsfield425 Properties
  • Woodstock302 Properties
  • Jamaica274 Properties
  • Plymouth268 Properties
  • Brattleboro257 Properties
  • Stratton Mountain235 Properties
  • Jay232 Properties
  • Middlebury230 Properties
  • Rutland205 Properties
  • Londonderry203 Properties
  • Manchester200 Properties
  • Montpelier199 Properties
  • Colchester197 Properties
  • South Hero193 Properties
  • Morrisville178 Properties
  • Waterbury165 Properties
  • East Burke157 Properties
  • Arlington137 Properties