Bennington Vacation Rentals

Our Favorite Vacation Rentals in Bennington

  • Mountain Retreat
    ExcellentChalet
    Booking.com
    From
    $150
  • Mountaintop Cabin w/Waterfront & Amazing View
    Good2br Chalet
    HolidayLettings
    From
    $229
  • CH# 274
     Country House
    Booking.com
    From
    $435
  • #223: 9 Spruce Grove Rd 223-01
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $670
  • Tentrr – Hidden Hoosic Riverside Camp
     Country House
    Booking.com
    From
    $174
  • Wilmington Home w/Pool Access- 20 Mins to Mt. Snow
     3br Home/Apartment
    HolidayLettings
    From
    $346
  • CH# 223
     Country House
    Booking.com
    From
    $420
  • Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access
     3br Home/Apartment
    HolidayLettings
    From
    $395

Check prices for these upcoming dates

Bennington Vacation Rentals with a Pool

  • Mountain Log Cabin
     3br Home/Apartment
    Airbnb
    From
    $339
  • Karin's Place: A Secluded Retreat
    Excellent9br Home/Apartment
    Airbnb
    From
    $1,610
  • Wilmington VT log Cabin near Mt. Snow
     3br Home/Apartment
    Airbnb
    From
    $311
  • The Vermont Barn (Mount Snow)
    Good4br Farmhouse
    Airbnb
    From
    $466

Bennington Vacation Rentals with Wi-Fi

  • Linda's Moose Lodge Lake House
    Excellent2br Home/Apartment
    Airbnb
    From
    $229
  • Southern Vermont Getaway Woodford,VT
    Excellent3br Home/Apartment
    Airbnb
    From
    $201
  • Bennington Village Home on VT Rt.9
    Good2br Home/Apartment
    Airbnb
    From
    $126
  • Studio Retreat
    ExcellentStudio
    Airbnb
    From
    $101

Bennington Pet-Friendly Vacation Rentals

  • #522: 28 Lightning Ledge Way 522-02
     3br Home/Apartment
    HolidayLettings
    From
    $633
  • #214: 303 Chimney Hill Rd 214-03
     3br Home/Apartment
    HolidayLettings
    From
    $577
  • #585: 12 Lilla Lane 585-02
     3br Home/Apartment
    HolidayLettings
    From
    $464
  • Off the Grid Cabin ~ Escape to VT
    Excellent2br Home/Apartment
    Airbnb
    From
    $157

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
91 º38
6
82 º24
4
67 º0
6
62 º8
3
65 º-23
3
77 º-7
4
54 º3
2
71 º17
4
87 º38
2
90 º40
3
94 º45
5
92 º50
5
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Bennington. The warmest months in Bennington are June and May, when temperatures reach 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

  • — 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
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa

Vacation Rentals in Bennington

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, Priceline, Bed and Breakfast and more. AllTheRooms has 232 rentals, hotels and other great places to stay during your time in Bennington, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. If you are wanting to save money, the cheapest place to stay in Bennington is just $42 a night. An average rental in Bennington costs on average $144 per night.

Those looking to get some work done during their trip to Bennington can pick from 99 places to stay that include WiFi. We have 17 accommodations that include a breakfast included. You can maintain your workout regime by staying at one of 6 accommodations that provide gym facilities. Driving to Bennington? Then choose one of the 92 places to stay that comes with a parking spot included. We have 8 accommodations that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 31 accommodations that are designated as pet-friendly.

We aggregate vacation rentals, hotels and other bespoke accommodation types from many providers in Bennington, including 77 places to stay from Airbnb, 3 accommodations from Priceline and 3 places to stay from Bed and Breakfast

126 of the accommodations in Bennington have been reviewed and rated. 57% are rated excellent or good. 51 places to stay in are instantly bookable.

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