Photo by William E Berry Jr.

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Compare 34 Chalets in Windsor with updated reviews, rates, and availability.

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (29)
"We had a great stay here! Looked just like the pictures. We especially loved the hot tub. Would love to come back."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Okemo Mountain Chalet W/ Hot Tub and Game Room
9.8 out of 10, Exceptional, (151)
"Great property for large groups with plenty of space and amenities for everyone. Excellent communication from owner to ensure a perfect stay before, during and after."
Okemo Mountain Chalet W/ Hot Tub and Game Room
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
9.0 out of 10, Wonderful, (6)
"Great and responsive communication with owner. The house is exactly as advertised and works well with three bedrooms, two bathrooms that are quite lovely and very clean, and a very functional kitchen."
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
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4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
9.8 out of 10, Exceptional, (13)
"Beautiful home in a great location. We had a wonderful time"
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (115)
"We arrived on Thursday and checked out on Sunday morning. We were a group of 16 adult golfers. The house was perfect. It was close to the golf course and we even got some fishing in at Kent Pond nearby ( with a bald eagle sighting!). The guys loved the pool table and the hot tub. We lit a fire every night and had loads of room for a cornhole tourney. Easy to cook in the kitchen and the grill was perfect on the deck. Checkin and check out were easy and Carla was in touch at all the right times....
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
10.0 out of 10, Exceptional, (16)
"From my first inquiry Dave had been responsive snd helpful. Beautiful house and we couldn’t ask for closer to Okemo trails. So much room in the home for all 17 of us. A fall trip back might be in our future for leave changing views."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Cozy Creekside Chalet centrally located near 4 ski resorts
10.0 out of 10, Exceptional, (6)
"The location was great for skiing at Okemo, and the house was cozy and just the right size for two sets of parents and two tween girls. The kitchen was surprisingly well provisioned for a VRBO."
The price is SAR 1,024
SAR 2,200 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Cozy Creekside Chalet centrally located near 4 ski resorts
South View Chalet!
9.2 out of 10, Wonderful, (25)
"The house was perfect for our group. The outdoor space was great and the view is beautiful. Would certainly stay here again!"
South View Chalet!
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
10.0 out of 10, Exceptional, (32)
"We enjoyed our stay. Noreen was very responsive when we had questions. Great location to Okemo."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Tree Top Home with Hot Tub Near Killington & Okemo
Tree Top Home with Hot Tub Near Killington & Okemo
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
9.8 out of 10, Exceptional, (19)
"We were so happy with every aspect of our family’s spring break stay at this spacious, clean gem of a home. The kitchen was well epuipped for dining in when we wanted, and the bedrooms were clean and comfortable. Looking forward to a return visit!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
BearHaus- Central AC, HUGE Hot Tub, FirePit
10.0 out of 10, Exceptional, (1)
"Beautiful kitchen, great amenities, awesome location!"
The price is SAR 1,917
SAR 4,224 total
includes taxes & fees
1 Raj. - 2 Raj.
BearHaus- Central AC, HUGE Hot Tub, FirePit
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
10.0 out of 10, Exceptional, (2)
"Took a week long vacation with friends and this was the perfect place for us. A lot bigger than we had anticipated, equipped with every we needed and only a short 10 minute drive to Killington. The only issue we had was the wifi. We didn’t have any reception but luckily none of us needed to check in with work."
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
9.8 out of 10, Exceptional, (37)
"Great spot for a getaway. The property and surrounding area are very pretty."
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
BearVaria! Hot Tub, Deck, FirePit, Frisbee Golf
10.0 out of 10, Exceptional, (9)
"We really enjoyed the amenities at this property in a very nice secluded part of Killington! Fire pit, hot tub, grill, some disc golf baskets, it really was what we needed for a weekend away mtn biking with the guys. The property is a little older, but well furnished and comfortable beds and towels. Definitely recommend staying here! Also, the hosts were super responsive texting back, usually within 15 minutes for any questions. They were extremely accommodating with an early check in and a...
BearVaria! Hot Tub, Deck, FirePit, Frisbee Golf
Secluded 2600 sqft home 15 min from Okemo and Killington
10.0 out of 10, Exceptional, (3)
"We absolutely loved our time at this lovely rental! All amenities were as described. Beds were super comfy, sauna was terrific, kitchen was well equipped and the fireplace, cozy. Meg was super responsive. We would definitely rent again!"
Secluded 2600 sqft home 15 min from Okemo and Killington
Okemo 6 Bedroom Chalet.
9.4 out of 10, Exceptional, (21)
"House was beautiful, cozy, and clean. We had an issue with the hot tub on the first night with it being cold, but they had someone come out the next morning to get it back running and we were able to use it the second night. House is in a great location. No complaints. Would stay here again."
Okemo 6 Bedroom Chalet.
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
9.6 out of 10, Exceptional, (30)
"Great location! House had everything we needed. Property owner very flexible. Would definitely rent again!"
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6/ $550per night,
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
10.0 out of 10, Exceptional, (3)
"This home was perfect in every way! We enjoyed staying here and there was easy communication with property management that was promptly handled. We will try to book when we decide to return to Killington."
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
10.0 out of 10, Exceptional, (10)
"The house is beautiful and we enjoyed our stay! Just need a full length mirror in a bedroom otherwise perfect ski property!"
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
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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.

Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (32)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (176)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
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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