Search Chalets in Woodstock

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Compare 39 Chalets in Woodstock with updated reviews, rates, and availability.

Snow and ski sports
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
A view of the house looking up the driveway after some early season snow.
Okemo Mountain Chalet W/ Hot Tub and Game Room
9.8 out of 10, Exceptional, (150)
"This fantastic house is roomy, comfortable and welcoming. It had everything we needed. Three families could stay with children and not be crowded, although we were all adults and had only up to 10 at any given moment. The hot tub was lovely and the surrounding property just beautiful. A warning about the dirt road might be a good idea for us city folks though, lol. Loved it and already figuring out when we can come back!"
Okemo Mountain Chalet W/ Hot Tub and Game Room
Living 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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Living area
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
Our signature fieldstone fireplace in our huge great room.
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!
Front porch view from covered stairs
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (113)
"This house was everything we needed. Ample space for a large group. Tom and Carla were very responsive. Our group had a terrific experience!"
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
Main Family Room 3rd Floor
overlooking Sachem Ski Trail
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
Exterior
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!
Exterior
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
Exterior
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.
Step inside and discover the largest hot tub in the area, a luxurious oasis designed to provide unparalleled comfort and relaxation. It's the perfect retreat after a day of adventure.
BearHaus- Central AC, HUGE Hot Tub, FirePit
10.0 out of 10, Exceptional, (1)
"Beautiful kitchen, great amenities, awesome location!"
BearHaus- Central AC, HUGE Hot Tub, FirePit
Living area
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.
Exterior of the house with patio chairs and hot tub, perfect for outdoor relaxation.
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
Living area
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
View of house from top of driveway. Dec. 18th, 2020
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.
Exterior
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,
IMG 8280
Gnome Home Mountain Ski Chalet w/Sauna Killington
10.0 out of 10, Exceptional, (2)
"The Gnome Home was everything we hoped for and more. The hosts are so helpful with communication, especially when a hefty snow storm hit. The home is cozy, clean and very well stocked with everything you need."
Gnome Home Mountain Ski Chalet w/Sauna Killington
Living area
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
Exterior
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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See all available properties in Woodstock
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 Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, (7)
"The home is charming, immaculate and amidst woods with no neighbors in eye or earshot. It is on a dirt road, so an awd vehicle is a good idea. A stream runs along the driveway. The Ottauquechee River is across the road. The bathroom is on the first floor, and bedrooms on the second floor. The smoke detector goes off if you saute on the stove. I recommend learning how to turn off a wired in smoke detector. You should open the kitchen window when you saute, because most of the smoke detectors...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Front of property
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
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"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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