Windsor County

Find Chalets in Windsor County

Enter your dates for the latest hotel rates and availability.

Swipe down to view more
Filter by:
Hotel Star Rating
≤2345
Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

We found 19 Windsor County Chalets for you

Choose your travel dates to see the latest prices and deals.
Most Booked
Lowest price
Closest to downtown
Highest Rated
38

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

Hotels in Windsor County
Featured facilities: Hiking
Outstanding
13 reviews
9.8/10
Check availability
19

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
Great
9.0/10
Check availability
15

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Hotels in Windsor County
Featured facilities: Ski equipment rental
Outstanding
9.8/10
Check availability
You Might Like
Windsor County Hotels With BreakfastWindsor County Hotels With Twin RoomWindsor County Hotels With 1 Double BedWindsor County Hotels With Swimming PoolWindsor County Hotels With Free Cancellation
28

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

Hotels in Windsor County
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
10.0/10
Check availability
28

All-Season Lake Pauline Retreat, 2 mi to Okemo

Hotels in Windsor County
Featured facilities: Hiking
Very Good
2 reviews
8.0/10
Check availability
46

Cozy Log Cabin Short Drive to Okemo & Killington

Hotels in Windsor County
Featured facilities: Skiing, Hiking
Amazing
5 reviews
9.6/10
Check availability
38

Modern Mt. Ascutney Cabin - Beautiful Winter Getaway

Hotels in Windsor County
Featured facilities: Ski equipment rental, Kitchen
Outstanding
9.8/10
Check availability
42

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

Hotels in Windsor County
Featured facilities: Skiing, Hiking
Outstanding
19 reviews
10.0/10
Check availability
51

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

Hotels in Windsor County
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
20 reviews
10.0/10
Check availability
27

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

Hotels in Windsor County
Featured facilities: Skiing, Mountain climbing, Hiking
Outstanding
29 reviews
10.0/10
Check availability
See More Chalets in Windsor County

Frequently Asked Questions

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

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Windsor County this weekend is RUB 42,909 per night. For a 4-star hotel, the average cost is RUB 36,386 per night. If you're looking for a luxury experience, 5-star hotels in Windsor County this weekend typically cost RUB 55,416 per night.

How much do hotels in Windsor County cost per night during weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Windsor County during weekdays is RUB 34,328 per night. For a 4-star hotel, you can expect to pay around RUB 43,529 per night. If you're looking for a luxury stay, 5-star hotels in Windsor County generally cost RUB 42,907 per night on weekdays.

What are the best places to stay in Windsor County?

Some of the best places to stay in Windsor County are near popular attractions like AT trailhead Woodstock VT, offering easy access to key sights and amenities.

What hotel deals are available in Windsor County?

Trip.com offers multiple promotions and discounts all year round for both new users and loyal customers . Please check the promotions page to see what promotions are available now on Trip.com.