Windsor County

Find Windsor County Chalets

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We found 17 Windsor County Chalets for you

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Top Picks
Lowest Price
Closest to Downtown
Top Reviewed
35

Cozy Vermont Cabin at Trail End Ranch! the Best of VT is All Around You!

Hotels in Windsor County
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
5 reviews
10/10
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38

Sweeping Vermont Views from A Private, Designer, Ascutney Cabin

Hotels in Windsor County
Featured facilities: Ski equipment rental, Kitchen
Outstanding
16 reviews
10/10
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20

Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain

Hotels in Windsor County
Featured facilities: Ski equipment rental, Hiking, Kitchen
Amazing
5 reviews
9.4/10
Check Availability
39

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

Hotels in Windsor County
Featured facilities: Hiking, Kitchen
Outstanding
11 reviews
9.8/10
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43

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

Hotels in Windsor County
Featured facilities: Kitchen
Outstanding
5 reviews
10/10
Check Availability
43

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

Hotels in Windsor County
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
21 reviews
10/10
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25

Charming Pet-Friendly Retreat in the Vermont Woods

Hotels in Windsor County
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
16 reviews
10/10
Check Availability
39

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Hotels in Windsor County
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
10/10
Check Availability
45

Cozy Vermont Log Cabin Near Okemo & Killington

Hotels in Windsor County
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
14 reviews
9.8/10
Check Availability
9

Cozy Cabin near Okemo

Hotels in Windsor County
Featured facilities: Kitchen
Amazing
11 reviews
9.4/10
Check Availability
See all Chalets in Windsor County

Frequently Asked Questions

What are the best places to stay in Windsor County?

Some top places to stay in Windsor County are near popular attractions like AT trailhead Woodstock VT—so you can quickly get to top landmarks and amenities you need.

What is the average price of a hotel in Windsor County for this weekend?

According to Trip.com’s latest 12-month data, 3-star hotels in Windsor County have an average price of MYR 1,265 per night this weekend. For 4-star hotels, the average rate is MYR 2,860 per night. If you’re seeking luxury, 5-star hotels in Windsor County typically cost MYR 4,052 per night this weekend.

What is the average nightly price of hotels in Windsor County on weekdays?

Based on Trip.com’s latest 12-month data, the average nightly rate for 3-star hotels in Windsor County on weekdays is MYR 1,144. For 4-star hotels, the average cost is around MYR 2,466 per night. For a luxury stay, 5-star hotels in Windsor County generally have an average price of MYR 3,319 per night on weekdays.

How to get good deals on hotels in Windsor County?

Find the best hotel deals and promotions on Trip.com, available year-round for both first-time and loyal users. Please check the promotions page to see what promotions are available now on Trip.com.