Windsor County

Find Windsor County Chalets

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Hotel Star Rating
≤2345
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Amazing 9+Great 8+Good 7+Pleasant 6+

We found 18 Windsor County Chalets for you

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Top Picks
Lowest Price
Closest to Downtown
Top Reviewed
30

All-Season Lake Pauline Retreat, 2 mi to Okemo

Hotels in Ludlow
Featured facilities: Hiking
Amazing
36 reviews
9.4/10
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56

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Hotels in Ludlow
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
35 reviews
10/10
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9

Cozy Cabin near Okemo

Hotels in Ludlow
Featured facilities: Kitchen
Amazing
12 reviews
9.4/10
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45

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

Hotels in Ludlow
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
69 reviews
10/10
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11

Escape to Your Own Private Vermont Retreat

Hotels in Plymouth
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
32 reviews
10/10
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27

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Hotels in Ludlow
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
137 reviews
10/10
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44

Cozy Vermont Log Cabin Near Okemo & Killington

Hotels in Cavendish
Featured facilities: Skiing, Hiking, Kitchen
Outstanding
29 reviews
9.8/10
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22

Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

Hotels in Ludlow
Completely renovated 7 bedroom, 3 bathroom modern mountain house, located in Ludlow. Outdoor deck with BBQ, hot tub, across the street from the mountain shuttle. All rooms with smart Tvs, game room with billiards and board games, large chefs kitchen with dining room and kitchen island. Mudroom at back entry.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Please turn the thermostats to 62° before check out.Please make sure the hot tub is covered after each use,Please throw all the garbage in the outside bin and make sure that lid is closed.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
4 reviews
10/10
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28

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Hotels in Chester
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
14 reviews
10/10
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33

Okemoskichalet with Game Room & Hot Tub on Okemo Mt. 1 Mile to Base! Sleeps 12

Hotels in Ludlow
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
144 reviews
9.8/10
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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 HK$2,456 per night this weekend. For 4-star hotels, the average rate is HK$5,482 per night. If you’re seeking luxury, 5-star hotels in Windsor County typically cost HK$7,998 per night this weekend.

How much do hotels in Windsor County typically cost 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 HK$2,172. For 4-star hotels, the average cost is around HK$4,926 per night. For a luxury stay, 5-star hotels in Windsor County generally have an average price of HK$6,496 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.