Chalets in Windsor County

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Top Cities in Windsor County

Ludlow showing street scenes
ChaletsChalets

Ludlow

Ludlow

Our top choices for Windsor County chalets

Exterior

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, (37 reviews)
"Great stay"
United States
ali m.
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Property grounds

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)
"Very spacious, clean, great location for annual family ski trip"
United States
Sueyoung C.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Exterior detail

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, (29 reviews)
"Great pet friendly property perfectly located between Woodstock and Killington. "
United States
Norman Y.
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior

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)
"Our stay was great! House was excellent, location was perfect, and Dave was super accommodating!"
United States
Anna B.
Ski In/Out Luxury 8BR Okemo Chalet on Sachem Trail Sleeps 22 Adults
Terrace/patio

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)
"Everything was perfect. Great space to relax , visit and close to downtown Woodstock. Bedrooms were clean , comfortable and private bathroom made for an awesome , spacious family event. "
United States
Beth S.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
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, (133 reviews)
"Just a cute and warm home. Clean and comfortable."
United States
Barbara K.
Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
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
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
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 reviews)
"Private, great location, clean, comfortable, warm host"
United States
Marge S.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Outdoor spa tub

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 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 Hideaway – Secluded Woodland Chalet 7 minutes to Slopes & Village
Terrace/patio

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
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, (16 reviews)
"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
Outdoor dining

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)
"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
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
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 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is CA $292
CA $683 total
includes taxes & fees
Mar 24 - Mar 25
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

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 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
Exterior

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)
"My husband and I were looking for a quiet place to spend a weekend and Jake and Hannah’s place was perfect! We were close to restaurants, farmers market, arts and crafts fair! The house was clean, had everything we needed. The jacuzzi and the fire pit were perfect for the cool nights. Check in was easy, and Jake and Hannah were prompt to answer any questions. We would love stay again! Thank you for sharing your house! "
United States
Kristina P.
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
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, (12 reviews)
"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
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 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
Exterior

Cozy 3-Bedroom Mountain Style Home

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

On The River Inn

On The River Inn

10/10 Excellent
"We loved our stay and the staff were the best. Shoutout to Joshua!"
Seyed Behnam 2-night trip
Posted 2 hours ago
On The River Inn

Find out more about Windsor County

Windsor County Chalets information

Number of reviews
691
Accommodation
23 Chalets
Lowest Price
CA $683
Highest Price
CA $683

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