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

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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
The price is CA $202
CA $244 total
includes taxes & fees
Nov 15 - Nov 16
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
The price is CA $227
CA $271 total
includes taxes & fees
Nov 16 - Nov 17
Grand Summit Resort, A Vail Resorts Property
A cozy living room with a fireplace, a dining table set for a meal, and a kitchen in the background.

3. 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.
Deluxe King Room w/pull-out love seat and fireplace
A two-story house with a large porch and a pond in front.

4. 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.
Deluxe King, kitchenette, fireplace
A cozy room with a fireplace, a flat-screen TV mounted above it, and a dining table set with a bottle of champagne, a glass, and a plate of cheese and crackers.

5. 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.
Deluxe King Room w/fireplace and separate entrance
A two-story house with a large porch and a pond in front.

6. 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
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

7. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
Deluxe King - 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

8. Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
Deluxe King- 2nd floor in Historic Inn
A room with two brown leather armchairs, a wooden coffee table with a bowl and a magazine, and a bed with pillows in the background.

9. 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.
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
A two-story house with a large porch and a pond in front.

10. Luxury King w/balcony, accessible

Luxury King w/balcony, accessible
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."
United States
Kimberley B.
Luxury King w/balcony, accessible
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

11. Luxury King with balcony

Luxury King with balcony
West Dover
Luxury King with balcony
A two-story house with a large porch and a pond in front.

12. 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.
King with Bunk Bed- 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

13. Deluxe King Suite, Living Room w/sofa bed & fireplace

Deluxe King Suite, Living Room w/sofa bed & fireplace
West Dover
10.0 out of 10, Exceptional, (1 review)
"My husband and I really enjoyed the accommodations. Great location with tons do do nearby. The place was so cozy and inviting. Would definitely stay again"
United States
Megan M.
Deluxe King Suite, Living Room w/sofa bed & fireplace
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

14. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
Deluxe King - 2nd floor in Historic Inn
A modern bedroom with a bed, bedside tables, a dresser, and a fireplace.

15. 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.
Deluxe 2xQueen & fireplace
A bedroom with a large bed, a wooden headboard, a nightstand, and a bench.

16. Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
West Dover
8.0 out of 10, Very good, (1 review)
"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."
United States
Craig C.
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
A two-story house with a large porch and a pond in front.

17. Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
United States
Jessica
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
A hotel room with two single beds, a wooden headboard, a small bedside table, and a nightstand with a lamp.

18. 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.
Deluxe 2xQueen- 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

19. Deluxe King, Living Room w/sofa bed & fireplace

Deluxe King, Living Room w/sofa bed & fireplace
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Had a really nice time - the place was lovely. They had some on property activities and were very close to the mountain. We had a great time and would definitely stay here again if back in the area!"
United States
Taylor G.
Deluxe King, Living Room w/sofa bed & fireplace
A hotel room with two beds, a desk, a TV, and a window with a city view.

20. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very good, (1 review)
Deluxe 2xQueen 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.
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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 less than an hour ago
Vermont Downtown Oasis - Two Bedroom in Picturesque Downtown

Find out more about Bennington

Bennington Resorts information

Number of reviews
36
Accommodation
1 Resorts
Lowest Price
CA $244
Highest Price
CA $271

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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