Top Chalets in Windsor County in 2026

A river flowing through a forest with autumn foliage.

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Top Cities in Windsor County

A red convertible car parked in front of a brick house with black shutters and a white picket fence.

Our top choices for Windsor County chalets

A covered outdoor area with a stone wall, a metal railing, and a view of autumn foliage and mountains.

1. Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ludlow

Jason B.

A wooden deck with four Adirondack chairs and a small table.

2. Okemo Mountain Chalet W/ Hot Tub and Game Room

Ludlow

"This is a spacious, comfortable property with everything you might need available on site. It is close to town with many shops and close to the mountain and all of those activities. We enjoyed a wonderful family weekend of hiking, exploring the swimming holes, going into town. We also just relaxed at the chalet along with our teen son and 20 something’s and their significant others. We all loved the space and would be happy to stay here again."

Letitia B.

A two-story house with a covered porch, outdoor seating, and string lights.

3. Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Woodstock

ted d.

A hot tub on a wooden deck with a view of a forest and a lake.

4. Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Chester

Mark R.

A deck with a table and chairs, an umbrella, and a view of a forest.

5. Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

Woodstock

Cindy A.

A two-story wooden cabin with a balcony, surrounded by autumn foliage.

6. Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 mile to base! Sleeps 12

Ludlow

Julianne M.

A wooden deck with a bench, overlooking a grassy area with tall trees and distant mountains.

7. Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Ludlow

Craig L.

A rustic wooden cabin with a steeply pitched roof, a wooden staircase leading to a deck, and surrounded by lush greenery.

8. Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

Stockbridge

Brendan H.

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Top Windsor County Hotel Reviews

Align Inn Vermont

10/10 Excellent

"Beautiful little hotel, loved that I could park the car in front of the room. Excellent location if visiting Woodstock, real close to the quechee gorge."