Bennington Cottages

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

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Our top choices for Bennington cottages

1. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Stratton

includes taxes & fees

10 Sept - 11 Sept

A house with a gravel driveway, surrounded by trees and a well-maintained lawn.

2. Peaceful Cottage Retreat

cambridge

Victor L.

includes taxes & fees

1 Oct - 2 Oct

A cabin with a wooden deck, a covered porch, and a gravel driveway.

3. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

includes taxes & fees

10 Sept - 11 Sept

A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

4. Terrific 3-bedroom cottage with AC in charming Cavendish

Cavendish

Mark G.

includes taxes & fees

14 Sept - 15 Sept

A wooden deck with picnic tables and chairs, surrounded by dense trees and a clear sky.

5. Hilltop Cottage

Argyle

Anna Z.

includes taxes & fees

10 Sept - 11 Sept

A wooden deck leading to a house with a view of a road and greenery.

6. Spacious Vermont Farmhouse 3 Mi to Mount Snow

West Dover

includes taxes & fees

30 Sept - 1 Oct

A green wooden house with a sloped roof and a front porch.

7. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Ludlow

includes taxes & fees

10 Sept - 11 Sept

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Top Bennington Hotel Reviews

The Four Chimneys Inn

10/10 Excellent

"Very nice, quiet place. Relaxing and cute."

Cozy Loft steps from VT Downtown

10/10 Excellent

"The place is wonderful! I stayed for almost a week and to have a little loft apartment to myself was great. I was in Bennington for a charged week-long bird-carving seminar and I was even disappointed that I didn't get to spend more time at the loft. It's warm, modernized and very inviting, has all aspects that make it feel like a home-away-from-home. Little issues I had trouble with, such as connecting the tv to the network and an AC-maintenance requirement were immediately and effectively addressed by the host. I would love to stay there every year upon my return to Bennington, VT."

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