Chalets in Windsor County

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Our top choices for Windsor County chalets

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Ludlow
9.6 out of 10, Exceptional, (39 reviews)
"Great location for a family of five to enjoy a ski trip!"
United States
Jason B.
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,

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, (12 reviews)
"Great location to the slopes!Comfortable house layout for a multiple families.Nice kitchen too."
United States
Kim H.
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo

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

Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
ludlow
10.0 out of 10, Exceptional, (30 reviews)
"Location was perfect, drops you right on the Sachem run. The house was welcoming and fantastic for our large group of multiple families, and the host was helpful and available for any questions. It was a great stay and would love to stay again!"
United States
Wendy N.
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults

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 reviews)
"Great space for large family gathering! "
United States
ted d.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

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

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. The house had the perfect amenities for our family ski weekend. Hoping we can come again! "
United States
Hilary S.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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, (133 reviews)
"We had a great stay. Close to the ski slope! Loved the wood stove after a day of skiing. Made the house cozy and warm. "
United States
Julianne M.
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

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, (47 reviews)
"Great communication, very nice place and close to the mountain "
United States
Craig L.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

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 reviews)
"Great cabin with lots of room. Secluded on a country road but very close to town. We had a wonderful stay. "
United States
Mark R.
Spacious 5-bedroom chalet with AC and WiFi in charming Chester

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
9.4 out of 10, Exceptional, (6 reviews)
"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

Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village

Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village
Ludlow
9.4 out of 10, Exceptional, (27 reviews)
"We had a wonderful stay! We hope to book again in the future. "
United States
Jenn F.
Okemo Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village

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, (53 reviews)
"Private, great location, clean, comfortable, warm host"
United States
Marge S.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

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, (30 reviews)
"The house was exceptionally clean, so much room for large groups to stay, also in a great spot close to mountains! "
United States
Alessandra L.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

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, (73 reviews)
"Wonderful spot -- loved using the sauna! Owners extraordinarily responsive on any question and issue. If you are looking for a quiet, expansive and uniquely comfortable space in this part of the world, this is the one!"
United States
Brian R.
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

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, (164 reviews)
"Perfect for our multi-generational family get together!"
United States
Michael B.
Okemo Mountain Chalet W/ Hot Tub and Game Room

Pet-friendly retreat in the Vermont woods near Ludlow

Pet-friendly retreat in the Vermont woods near Ludlow
Plymouth
10.0 out of 10, Exceptional, (15 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
Pet-friendly retreat in the Vermont woods near Ludlow

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, (16 reviews)
"Exceptional spot for a family getaway - close proximity to Okemo Mountain. The home is beautifully designed, spotlessly clean and the hosts thought of everything to make it a comfortable and inviting stay. Highly recommend! "
United States
Elizabeth M.
Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
Gnome Home Mountain Ski Chalet w/Sauna Killington

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

Cozy 3-Bedroom Mountain Style Home

Cozy 3-Bedroom Mountain Style Home
Reading
Cozy 3-Bedroom Mountain Style Home

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