Silk Road covered bridge with trees showing fall colors near Paper Mill Village, Vermont.

Search Resort Hotels in Bennington from CA $234

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Bennington resorts

Free WiFi, bed sheets

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (996 reviews)
"Amazing hotel"
United States
Luis
The price is CA $193
CA $234 total
includes taxes & fees
Jul 5 - Jul 6
The Black Bear Lodge at Stratton Mountain Resort
Exterior

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, (277 reviews)
"Excellent stay, looking forward to visiting again!"
United States
Jordyn C
The price is CA $216
CA $259 total
includes taxes & fees
Jul 13 - Jul 14
Grand Summit Resort, A Vail Resorts Property
Dining

Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfect"
United States
James R.
The price is CA $388
CA $631 total
includes taxes & fees
Jun 21 - Jun 22
Deluxe King Room w/pull-out love seat and fireplace
Exterior

Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"End of season special. Perfect size, fireplace was great on a cold rainy night. Last night restaurant was open for a few weeks."
United States
john L.
The price is CA $421
CA $672 total
includes taxes & fees
Jun 21 - Jun 22
Deluxe King, kitchenette, fireplace
Interior

Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
The price is CA $388
CA $631 total
includes taxes & fees
Jun 23 - Jun 24
Deluxe King Room w/fireplace and separate entrance
Exterior

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Dover
9.4 out of 10, Exceptional, (6 reviews)
"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "
United States
Olivia
The price is CA $421
CA $672 total
includes taxes & fees
Jun 23 - Jun 24
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."
United States
Brendan M.
The price is CA $340
CA $570 total
includes taxes & fees
Jun 23 - Jun 24
Deluxe 2xQueen- 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dover
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, cozy and comfortable. The whole estate is beautiful."
United States
Mike T.
The price is CA $421
CA $672 total
includes taxes & fees
Jul 5 - Jul 6
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen & fireplace

Deluxe 2xQueen & fireplace
Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful Inn however, the fridge should be lifted off the floor. It’s too low. A small broom and dust pan would be nice to sweep up the dirt that treks in from the dirt parking lot and walk ways. Upgrade full size beds to at least two Queen size beds."
United States
Christina R.
The price is CA $340
CA $570 total
includes taxes & fees
Jul 1 - Jul 2
Deluxe 2xQueen & fireplace
Exterior

King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
The price is CA $388
CA $631 total
includes taxes & fees
Jun 23 - Jun 24
King with Bunk Bed- 2nd floor in Historic Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

South Shire

South Shire

10/10 Excellent
"South Shire is a quaint Victorian Inn on Elm Street within walking distance to the center of Bennington, VT. The Inn has a family feel and elegance. We traveled as a couple. It was easy to get to sites and enjoy fine restaurants. The Inn is in keeping with the feel of strength of the Bennington community, as a place for artists, musicians, and people's expression generally to thrive. We enjoyed our stay and would recommend South Shire."
Peter 2-night trip
Posted 2 days ago
South Shire

Find out more about Bennington

Bennington Resorts information

Number of reviews
1,299
Accommodation
11 Resorts
Lowest Price
CA $234
Highest Price
CA $672

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 Equinox Golf Resort And Spa - Luxury resort. 20.5 mi (33 km) from Bennington. Has 4 restaurants, 2 bars, and a golf course. 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. Enjoy the 10 restaurants, 2 bars, and sauna. 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. Palmer House Resort - Deluxe King Bed 5 - Golf resort. 22.1 mi (35.6 km) from Bennington. Access to a garden, free breakfast, and an indoor pool.
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 Bennington Potters Yard or Fiddlehead at Four Corners for some retail therapy. Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Center for the Arts 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.

Explore a world of travel with Expedia