A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Best Resorts in Bennington

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Bennington resorts

A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.

1. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.8 out of 10, Good, (1,000 reviews)
"Great place to stay"
United States
Joseph
$151 nightly
The price is $166
Nov 15 - Nov 16
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
A red building with a stone fire pit and outdoor seating.

2. Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (332 reviews)
"We went for a wedding and couldn’t have been happier with our stay."
United States
Kevin
$173 nightly
The price is $190
Nov 16 - Nov 17
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

10/10 Excellent
"We loved our stay! Chris as extremely communicative and accommodating. 10/10 highly recommend."
Angela R. 14-night trip
Posted 18 hours ago
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Find out more about Bennington

Bennington Resorts information

Number of reviews
Accommodation
1 Resorts
Lowest Price
$166
Highest Price
$190

Frequently asked questions

What can I expect from a resort vacation in Bennington?
Longing for a relaxing escape? Indulge in all the comforts and luxuries of a resort, where you can find everything you want for your trip from tasty dining options to entertainment and shopping. Browse the resorts in the area and discover the one that's best for you, whether you picture yourself sitting down to fine dining or hitting the golf course for an afternoon game.
What's the best resort in Bennington?
Our highest-rated resorts around Bennington: Grand Summit Resort, A Vail Resorts Property - Ski resort, 5-minute walk from Green Mountain National Forest. 17.2 mi (27.7 km) from Bennington. Features ski-in/ski-out access, a full-service spa, and a fitness center. The Black Bear Lodge at Stratton Mountain Resort - Ski resort, 5-minute walk from Green Mountain National Forest. 22.3 mi (35.9 km) from Bennington. Has 10 restaurants, 2 bars, and a sauna. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 23 mi (37 km) from Bennington. Enjoy the ski-in/ski-out access, fitness center, and garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 22.9 mi (36.9 km) from Bennington. Amenities include ski-in/ski-out access, a fitness center, and beach sun loungers. King with Bunk Bed- 2nd floor in Historic Inn - Situated just a 5-minute walk from Green Mountain National Forest. 18.6 mi (30 km) from Bennington. Access to a car charging station.
What can I do in Bennington?
Travelers come to Bennington for winter sports like skiing, and also love the shopping and other activities. Check out the interesting exhibits at Bennington Museum and Robert Frost Stone House Museum, or head to Fiddlehead at Four Corners or Bennington Potters Yard for some retail therapy. Prospect Mountain Cross-Country Ski Center and Woodford State Park are a few additional attractions in the area that you might like.
What's the seasonal weather like in Bennington?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Bennington are January, March, February, and December, with each month seeing an average of 8 inches of snowfall.
What's the best way to get to and around Bennington?
Fly into Albany Intl. Airport (ALB), which is located 31.7 mi (51 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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