Chalets in Windsor County

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Windsor County

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,

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

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.

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

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)
"It was exactly as described. The host was very helpful and responsive. It was perfect for our family getaway!!!! "
United States
Jeannine F.
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!

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

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

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

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

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

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

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

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

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

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

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.
The price is HK$1,620
HK$3,790 total
includes taxes & fees
30 Apr - 1 May
Gnome Home Mountain Ski Chalet w/Sauna Killington

Bent Tree

Bent Tree
3.5 star property
Stockbridge
Bent Tree

Cozy 3-Bedroom Mountain Style Home

Cozy 3-Bedroom Mountain Style Home
Reading
Cozy 3-Bedroom Mountain Style Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor County Hotel Reviews

Find out more about Windsor County

Windsor County Chalets information

Number of reviews
656
Accommodation
23 Chalets
Lowest Price
HK$3,790
Highest Price
HK$3,790

Explore a world of travel with Expedia