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Find Chalets in Windsor County, VT from $482

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Dec 19 - Dec 21
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In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Top Cities in Windsor County

Ludlow showing street scenes
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Ludlow

Ludlow

Chalets in Windsor County

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

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

Plymouth
9.8 out of 10, Exceptional, (25)
"The cabin was spacious and well stocked. It’s on a quiet dirt-road which made it perfect for our kids and dog to play and run outside. We really enjoyed our time close to some beautiful lakes, hikes and bike rides."
United States
Fabienne M.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

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

Ludlow
10.0 out of 10, Exceptional, (40)
"This was our 2nd year in a row staying at Noreen’s place. The property is breathtaking, the house is well appointed with comfy beds, solid WiFi and a great kitchen. We had 6 adults and 7 kids and the space never felt cramped, but for us the real show stopper is the side yard and deck. Awesome views, one of the best fire pits I have ever seen and a lawn worthy of many kids games. Extra bonus this year was clear weather to see the Presides meteor shower at night. We can’t wait to stay again next...
United States
Philip C.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior
Cozy Creekside Chalet centrally located near 4 ski resorts

Cozy Creekside Chalet centrally located near 4 ski resorts

Weston
10.0 out of 10, Exceptional, (16)
"An attractive home in a nice area. The hosts are very kind people and very accommodating. I would stay again. The location is convenient to many interesting places. "
United States
Ed C.
Cozy Creekside Chalet centrally located near 4 ski resorts
Exterior
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

Ludlow
9.8 out of 10, Exceptional, (128)
"Spacious, clean, beautiful property, well-stocked, host extremely responsive "
United States
Lisa D.
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
Exterior
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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

Chester
10.0 out of 10, Exceptional, (10)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Terrace/patio
Okemo 6 Bedroom Chalet.

Okemo 6 Bedroom Chalet.

Ludlow
9.4 out of 10, Exceptional, (23)
"We were up for a weekend in February. Perfect place. Plenty of beds. The hot tub was a bonus. Excellent communication by the hosts. "
United States
Tom G.
Okemo 6 Bedroom Chalet.
Exterior
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 Adults

ludlow
10.0 out of 10, Exceptional, (29)
"Absolutely amazing property!! Tons of room for everyone and very comfortable!! We had the best time!!"
United States
Anonymous traveler
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Exterior
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

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

Woodstock
10.0 out of 10, Exceptional, (27)
"Great space for large family gathering! "
United States
ted d.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Exterior
Okemo Mountain Chalet W/ Hot Tub and Game Room

Okemo Mountain Chalet W/ Hot Tub and Game Room

Ludlow
9.8 out of 10, Exceptional, (161)
"Perfect for our multi-generational family get together!"
United States
Michael B.
Okemo Mountain Chalet W/ Hot Tub and Game Room
Exterior
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
$515 nightly
The price is $576
Dec 15 - Dec 16
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Outdoor spa tub
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Plymouth
9.8 out of 10, Exceptional, (37)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
United States
Ross D.
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Exterior
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

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

Stockbridge
9.6 out of 10, Exceptional, (52)
"Beautiful property"
United States
sheri n.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Exterior
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

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

Ludlow
10.0 out of 10, Exceptional, (10)
"Great house, made our ski weekend easy and fun. House is better than the pictures."
United States
Trevor D.
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Exterior
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

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

West Woodstock
10.0 out of 10, Exceptional, (70)
"The house was very clean and tidy. Kat was great at communicating and making sure we had everything we needed!"
United States
Kevin P.
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Property grounds
Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge
10.0 out of 10, Exceptional, (4)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
$457 nightly
The price is $482
Dec 9 - Dec 10
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
Terrace/patio
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

Cavendish
10.0 out of 10, Exceptional, (14)
"We had a fantastic stay at the Honeycomb Hideout. The house is very well maintained and has everything you need. The weather didn't hold out for us but having a great place to stay made up for it!"
United States
Michael K.
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow
Terrace/patio
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 Mountain

Chester
9.2 out of 10, Wonderful, (5)
"We had a blast and had fund using the hot tub and firepit."
United States
Victoria H.
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Outdoor spa tub
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

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

Chester
10.0 out of 10, Exceptional, (8)
"Girls family weekend, relaxing, visiting and enjoying the hot tub."
United States
Sarah D.
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Exterior
Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond

Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond

Plymouth
Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond
Front of property
Bent Tree

Bent Tree

3.5 star property
Stockbridge
Bent Tree
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor County Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 11 hours ago
Pointe at Castle Hill Resort

Find out more about Windsor County

Windsor County Chalets information

Number of reviews
564
Accommodation
23 Chalets
Lowest Price
$482
Highest Price
$576

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