Bennington Vacation Rentals

Our Favorite Vacation Rentals in Bennington

  • Mountain Retreat
     Chalet
    Booking.com
    From
    $185
  • Mountaintop Cabin w/Waterfront & Amazing View
    Good2br Chalet
    HolidayLettings
    From
    $229
  • Karin's Place
     7br Home/Apartment
    Flipkey
    From
    $1,868
  • NEW! Wilmington Home w/Deck, Lake View & Game Room
     5br Home/Apartment
    HolidayLettings
    From
    $903
  • Wilmington Home w/Pool Access- 20 Mins to Mt. Snow
     3br Home/Apartment
    HolidayLettings
    From
    $346
  • Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access
     3br Home/Apartment
    HolidayLettings
    From
    $408
  • #164: 16 Big Bend Loop 164-03
     4br Country House
    HolidayLettings
    From
    $550
  • #214: 303 Chimney Hill Rd 214-03
     3br Home/Apartment
    HolidayLettings
    From
    $577

Check prices for these upcoming dates

Bennington Vacation Rentals with a Pool

  • Cozy house on the hill
    Excellent3br Home/Apartment
    Airbnb
    From
    $424
  • Karin's Place: A Secluded Retreat
    Excellent9br Home/Apartment
    Airbnb
    From
    $1,610
  • 4 bedroom Ski House 15 min to Mount Snow
    Excellent4br Home/Apartment
    Airbnb
    From
    $410
  • Hillside Haven: Mount Snow - Ski Patrol Discount
    Excellent3br Home/Apartment
    Airbnb
    From
    $513

Bennington Vacation Rentals with Wi-Fi

  • Linda's Moose Lodge Lake House
    Excellent2br Home/Apartment
    Airbnb
    From
    $229
  • Post & Beam on Stamford Stream in VT Nat’l Forest
    Excellent2br Home/Apartment
    Airbnb
    From
    $273
  • Southern Vermont Getaway Woodford,VT
    Excellent3br Home/Apartment
    Airbnb
    From
    $201
  • Private Compound, Green Mtn. Nat’t Forest
     3br Home/Apartment
    Airbnb
    From
    $655

Bennington Pet-Friendly Vacation Rentals

  • #A2: 173 Howes Loop A002-01
     3br Home/Apartment
    HolidayLettings
    From
    $689
  • Woodford Cabin in the Woods
    Excellent2br Home/Apartment
    Airbnb
    From
    $174
  • Off the Grid Cabin ~ Escape to VT
    Excellent2br Home/Apartment
    Airbnb
    From
    $145
  • 426 sf cabin! Private! Remote!
    GoodHome/Apartment
    Airbnb
    From
    $146

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
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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
67°
6
62°
3
65° -23°
3
77° -7°
4
54°
2
71° 17°
4
87° 38°
2
90° 40°
3
94° 45°
5
92° 50°
5
91° 38°
6
82° 24°
4
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Bennington. The hottest month in Bennington is June, when temperatures peak at 94 ˚F. The coolest month is December, when temperatures drop to -23 ˚F. The wettest month in Bennington is February with 5.74 inches of rain, while the driest month is August with 1.85 inches of rain.

What Expert Travelers Think

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Vacation Rentals in Bennington

Browse places to stay from all the best providers including Airbnb, Priceline, Bed and Breakfast and many more at AllTheRooms.com. Bennington has 236 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, extravagant travelers and everything in between. A vacation in Bennington can be budget-friendly - our cheapest price vacation rental is available at $42 per night. On average, a place to stay in Bennington will cost you $144 per night.

If you need an internet connection during your time in Bennington, then you can choose from over 87 accommodations that provide WiFi internet. 19 places to stay include a breakfast. Fitness fanatics can get a workout in during their stay by choosing from 5 accommodations that have gyms. If you're planning on arriving in Bennington by car, be sure to choose from 82 accommodations that provide parking. 8 accommodations have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 26 accommodations that are designated as pet-friendly.

We combine a wide variety of Bennington accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 79 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from Bed and Breakfast.

123 accommodations in Bennington have been reviewed; 63% are rated excellent or good. 55 places to stay in are instantly bookable.

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