Windsor County

Find Chalets in Windsor County

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Amazing 9+Great 8+Good 7+Pleasant 6+

We found 19 Chalets in Windsor County for you

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Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 AdultsLuxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 AdultsLuxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 AdultsLuxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 AdultsLuxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 AdultsLuxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
57
Hotels in Windsor County
Featured facilities: Skiing, Hiking
Outstanding
20 reviews
10.0/10
Check Availability
Delightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trails
Delightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trailsDelightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trailsDelightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trailsDelightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trailsDelightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trailsDelightful Vacation Home - Minutes to Okemo,  Direct Access to VAST trails
42
Hotels in Windsor County
Featured facilities: Skiing, Hiking
Outstanding
19 reviews
10.0/10
Check Availability
Cozy Cabin near Okemo
Cozy Cabin near OkemoCozy Cabin near OkemoCozy Cabin near OkemoCozy Cabin near OkemoCozy Cabin near OkemoCozy Cabin near Okemo
9
Hotels in Windsor County
Cozy private cabin located just 10 minutes from Okemo! This cabin features a mud room to store all your ski gear. One bedroom with a double bed, double sized bunk bed, and mini crib. The living room features a 60” TV and pull out couch. Bring your snowmobiles for direct access to the VAST trails across the street.About pets:Pets allowed: dogs (limit 1 total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:-Keep food and drinks in kitchen and dining area. -Please do all your dishes - Any dirty towels place in tub - Do not leave trash/ food outside.When leaving the house and when checking out unplug all space heaters and turn heat down to low "L" in the winter. In the summer keep heater unplugged.About checkIn:Check in after 3:30 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Amazing
5 reviews
9.6/10
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Windsor County
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Cozy Log Cabin Short Drive to Okemo & Killington
Cozy Log Cabin Short Drive to Okemo & KillingtonCozy Log Cabin Short Drive to Okemo & KillingtonCozy Log Cabin Short Drive to Okemo & KillingtonCozy Log Cabin Short Drive to Okemo & KillingtonCozy Log Cabin Short Drive to Okemo & KillingtonCozy Log Cabin Short Drive to Okemo & Killington
48
Hotels in Windsor County
Featured facilities: Skiing, Hiking
Amazing
5 reviews
9.6/10
Check Availability
All-Season Lake Pauline Retreat, 2 mi to Okemo
All-Season Lake Pauline Retreat, 2 mi to OkemoAll-Season Lake Pauline Retreat, 2 mi to OkemoAll-Season Lake Pauline Retreat, 2 mi to OkemoAll-Season Lake Pauline Retreat, 2 mi to OkemoAll-Season Lake Pauline Retreat, 2 mi to OkemoAll-Season Lake Pauline Retreat, 2 mi to Okemo
28
Hotels in Windsor County
Featured facilities: Hiking
Very Good
2 reviews
8.0/10
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Modern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets Welcome
Modern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets WelcomeModern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets WelcomeModern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets WelcomeModern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets WelcomeModern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets WelcomeModern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets Welcome
38
Hotels in Windsor County
Featured facilities: Ski Equipment Rental, Kitchen
Outstanding
15 reviews
9.8/10
Check Availability
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
22
Hotels in Windsor County
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 minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
5 reviews
10.0/10
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Pet-Friendly Winter Retreat in the Woods Near Okemo + Killington
Pet-Friendly Winter Retreat in the Woods Near Okemo + KillingtonPet-Friendly Winter Retreat in the Woods Near Okemo + KillingtonPet-Friendly Winter Retreat in the Woods Near Okemo + KillingtonPet-Friendly Winter Retreat in the Woods Near Okemo + KillingtonPet-Friendly Winter Retreat in the Woods Near Okemo + KillingtonPet-Friendly Winter Retreat in the Woods Near Okemo + Killington
42
Hotels in Windsor County
Featured facilities: Skiing, Hiking
Outstanding
14 reviews
10.0/10
Check Availability
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Cozy 4bd - Ski Okemo, Killington, Magic & BromleyCozy 4bd - Ski Okemo, Killington, Magic & BromleyCozy 4bd - Ski Okemo, Killington, Magic & BromleyCozy 4bd - Ski Okemo, Killington, Magic & BromleyCozy 4bd - Ski Okemo, Killington, Magic & BromleyCozy 4bd - Ski Okemo, Killington, Magic & Bromley
28
Hotels in Windsor County
Featured facilities: Skiing, Mountain Climbing
Outstanding
2 reviews
10.0/10
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Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo MountainModern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo MountainModern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo MountainModern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo MountainModern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo MountainModern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
19
Hotels in Windsor County
Featured facilities: Ski Equipment Rental, Hiking
Great
5 reviews
9.0/10
Check Availability
See all Chalets in Windsor County

Frequently Asked Questions

What are the must-visit spots in Windsor County?

Windsor County is home to iconic landmarks such as AT trailhead Woodstock VT.

What’s the average hotel price in Windsor County this weekend?

The average prices for hotels in Windsor County this weekend are as follows:
3-star hotels: AU$ 846
4-star hotels: AU$ 739
5-star hotels: AU$ 1,224

How much do hotels in Windsor County usually cost on weekdays?

On average, hotel prices in Windsor County on weekdays are approximately:
3-star hotels: AU$ 659
4-star hotels: AU$ 853
5-star hotels: AU$ 912