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
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

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
7.6 out of 10, Good, (1,002 reviews)
"friendly, helpful staff and very clean accommodations"
United States
DENNIS
The price is CA $187
CA $226 total
includes taxes & fees
Sep 30 - Oct 1
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, (312 reviews)
"Room was clean, the staff was friendly and helpful. We would stay again."
United States
Daniel
The price is CA $212
CA $254 total
includes taxes & fees
Oct 28 - Oct 29
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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
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.
The price is CA $503
CA $775 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King, kitchenette, fireplace
A two-story house with a large porch and a pond in front.

5. 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 $503
CA $775 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
A hotel room with two single beds, a wooden headboard, a small bedside table, and a nightstand with a lamp.

6. 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 $421
CA $672 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe 2xQueen- 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.

7. 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 $503
CA $775 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
A modern bedroom with a bed, bedside tables, a dresser, and a fireplace.

8. 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 $421
CA $672 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe 2xQueen & fireplace
A two-story house with a large porch and a pond in front.

9. 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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
Luxury King w/balcony, accessible
A two-story house with a large porch and a pond in front.

10. 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
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
A two-story house with a large porch and a pond in front.

11. 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.
The price is CA $503
CA $763 total
includes taxes & fees
Oct 5 - Oct 6
Deluxe King Suite, Living Room w/sofa bed & fireplace
A two-story house with a large porch and a pond in front.

12. 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.
The price is CA $503
CA $775 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King, Living Room w/sofa bed & fireplace
A two-story house with a large porch and a pond in front.

13. 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 $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
King with Bunk Bed- 2nd floor in Historic Inn
A hotel room with two beds, a desk, a TV, and a window with a city view.

14. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very good, (1 review)
The price is CA $421
CA $672 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe 2xQueen in Historic Inn
A cozy room with a fireplace, wooden beams, a bookshelf, and a television.

15. Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Dover
9.8 out of 10, Exceptional, (7 reviews)
The price is CA $519
CA $794 total
includes taxes & fees
Sep 29 - Sep 30
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
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.
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

17. Deluxe Queen Suite with pull-out love seat, private entrance

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
The price is CA $421
CA $672 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe Queen Suite with pull-out love seat, private entrance
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

18. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King - 2nd floor in Historic Inn
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

19. Luxury King with balcony

Luxury King with balcony
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
Luxury King with balcony
A two-story house with a large porch and a pond in front.

20. Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
The price is CA $454
CA $713 total
includes taxes & fees
Sep 29 - Sep 30
Deluxe King- 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.
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Top Bennington Hotel Reviews

South Shire

South Shire

10/10 Excellent
"I loved this beautiful inn! I felt like we were actually thrown back in time. So many cool things to see. There were no tv’s. It was NFL Sunday. At first, we were bummed but! We found a ton of fun games and played Yahtzee in the parlor. It was good to turn away from technology! Thank you for a wonderful stay!"
Lisa 1-night trip
Posted 4 hours ago
South Shire

Find out more about Bennington

Bennington Resorts information

Number of reviews
1,353
Accommodation
1 Resorts
Lowest Price
CA $226
Highest Price
CA $794

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 Bennington Potters Yard or Fiddlehead at Four Corners for some retail therapy. Bennington Center for the Arts and Prospect Mountain Cross-Country Ski Center 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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