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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)
"A fantastic and affordable spot right off the Sachem trail. This was my 3rd time staying here, and it just works out great for our family. "
Benjamin F.
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 Adultsludlow
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!"
Wendy N.
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. "
Julianne M.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to SkiWoodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great space for large family gathering! "
ted d.
Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Spacious 5-bedroom chalet with AC and WiFi in charming ChesterChester
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. "
Mark R.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4Stockbridge
9.6 out of 10, Exceptional, (53 reviews)
"Private, great location, clean, comfortable, warm host"
Marge S.
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 VillageWoodstock
10.0 out of 10, Exceptional, (75 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!"
Brian R.
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trailsLudlow
10.0 out of 10, Exceptional, (47 reviews)
"Great communication, very nice place and close to the mountain "
Craig L.
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
The Shire Woodstock
10/10 Excellent
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