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Chalet vacation rentals in Woodstock

Find and book unique chalets on Airbnb

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Popular amenities for Woodstock chalet rentals

Family-friendly chalet rentals

Guest favorite
A secluded chalet is surrounded by snow-covered trees, showcasing its wrap-around deck. The winter landscape features undisturbed snow blanketing the ground, while blue skies peek through scattered clouds above.
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars2 months ago
We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!
Guest favorite
Chalet in Killington
4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

ScottRating, 5 stars2 weeks ago
This is our second time renting Clinton's ski lodge place is great super host. Always responsive will be renting again next season.
Guest favorite
A spacious living area is showcased, featuring a red sectional sofa positioned around a round coffee table. Natural wood beams cross the ceiling, complementing the stone fireplace. Two modern chairs are arranged nearby, with a decorative plant on a side table, enhancing the welcoming ambiance.
Chalet in Waitsfield
4.96 out of 5 average rating, 141 reviews

Warm Luxury Mid-Century Modern Chalet

CaitlinRating, 5 stars3 weeks ago
This is the second time I’ve stayed at Sierra’s house, and we just love it! It’s comfortable, beautiful, Waitsfield is lovely, and we couldn’t have asked for anything else!
Guest favorite
A rustic ski chalet is nestled among snow-covered trees, with a sloping driveway leading to the entrance. The building showcases a wooden deck and vibrant blue exterior, surrounded by a serene winter landscape.
Chalet in Ludlow
4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

ChristopherRating, 5 stars3 months ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
A rustic chalet is surrounded by a spacious lawn, featuring natural stone elements and several outdoor seating areas. A fire pit is situated in the center, accompanied by Adirondack chairs. The front porch is visible, providing access to the inviting entrance of the home.
Chalet in Jamaica
4.78 out of 5 average rating, 453 reviews

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK

JasonRating, 5 stars2 weeks ago
The chalet is secluded, quiet and peaceful. We appreciated its location in the woodland, right near a stream. It was comfortable for our family and we would return again in the future.
Guest favorite
A contemporary ski house is featured, set against a snowy landscape. The structure showcases large glass windows and a spacious deck, elevated on stilts. Surrounding trees and a light dusting of snow enhance the serene atmosphere of the property, inviting a cozy retreat.
Chalet in Ludlow
4.95 out of 5 average rating, 128 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars4 weeks ago
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.
Guest favorite
A spacious living area is highlighted by large windows that bring in natural light and views of the greenery outside. Wooden beams adorn the ceiling, and a cozy sofa faces a coffee table, with a dining table and chairs nearby.
Chalet in Peru
4.85 out of 5 average rating, 89 reviews

Bromley Aframe - King Master Bed, Wood Fireplace

SamanthaRating, 5 stars2 months ago
All around a wonderful experience. Michael was lovely, super responsive and went out of his way to make sure we were comfortable. The house and amenities are well appointed. Bed was super comfy. Would absolutely stay again.
Guest favorite
The exterior of the upper unit duplex is surrounded by snow, showcasing a wooden deck with a railing and steps leading to the entrance. A prominent stone chimney rises from the roof, and large windows provide a view of the surrounding forest.
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars3 months ago
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

Luxury chalet rentals

Superhost
A pathway of wooden steps leads up to a charming house surrounded by lush greenery. The house features a spacious deck with a gentle curve, inviting outdoor relaxation. A gravel area provides ample parking space, blending seamlessly with the natural landscape.
Chalet in Killington
4.9 out of 5 average rating, 162 reviews

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

AndrewRating, 5 stars2 months ago
This was the second time we stayed here and had a great time. The location is great and the house is well maintained and comfortable. We'll definitely be returning!
Guest favorite
A well-lit living room features a spacious sectional sofa facing a fieldstone fireplace. A wooden coffee table sits centrally, and a Samsung flat-screen TV is mounted above the fireplace. Large windows provide natural light and views of the surrounding greenery, enhancing the serene setting.
Chalet in Killington
4.96 out of 5 average rating, 109 reviews

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

AlixRating, 5 stars3 months ago
We had a great weekend skiing at Killington and hanging at this lovely mountain house. The house was perfect for a group of couples. We loved the big open kitchen, huge sectional couch, and the hot tub. It was a 5 minute drive to many restaurants and fun bars, and a 7 minute drive to Killington lifts - super convenient and easy! We would definitely stay here again.
Top guest favorite
The exterior of the chalet is illuminated by string lights, creating a warm ambiance at night. The wooden structure features multiple balconies and large windows, while a spacious lawn is dotted with natural landscaping. A small shed is visible in the yard, adding to the outdoor charm.
Chalet in Mendon
5 out of 5 average rating, 48 reviews

Luxury Chalet - Secret Speakeasy- Near Killington

IanRating, 5 stars1 week ago
Our family had a wonderful time at Brian’s chalet. Our family of 5 (newborn, 3 year old, and 5 year old) spent a very memorable weekend up in the Vermont mountains at this lovely home. The kids room was spacious, had lots of sleeping options, and a wide variety of toys. My kids loved the basement/speakeasy hidden behind the wall shelf- and we enjoyed both the video games, shuffle board, and pool. The home was spotless, had all details considered- and made for a wonderful weekend stay. Highly recommend this charming chalet!
Top guest favorite
A hot tub is seen surrounded by lush trees, creating a private outdoor oasis. Two glasses on a ledge indicate a place for relaxation. White Adirondack chairs are positioned nearby, enhancing the inviting atmosphere of the serene forest setting.
Chalet in Sunderland
4.99 out of 5 average rating, 81 reviews

Serene & Stylish Chalet w/ HOT TUB near Manchester

MingRating, 5 stars1 day ago
Wonderful chalet close to all of the best of Southern Vermont. A nice blend of modern comfort and rustic surroundings. Beautiful private yard for roasting marshmallows and hot tubbing. Garrett was very responsive whenever we had a question or needed assistance. One of the most responsive hosts we’ve had over the past 10 years of using AirBNB. Super host indeed
Top guest favorite
A wooden deck is featured, showcasing a pair of woven chairs and a small table. The natural surroundings are visible through large windows and greenery creates a serene backdrop. The structure exudes a rustic charm, inviting relaxation in the fresh air.
Chalet in Stockbridge
4.94 out of 5 average rating, 48 reviews

BENT TREE Vermont, Mtn Chalet 25 min to Killington

PaulRating, 5 stars3 months ago
Beautiful location and very easy access to Killington Ski Resort! We had >1 foot of snow and the steep driveway was plowed well before departure. Very clear communication and instructions made for a very relaxing time. Thank you for sharing your home!
Guest favorite
A rustic treehouse is elevated among the trees, featuring an open deck and enclosed area. Surrounded by lush greenery, the structure offers a serene retreat in the forest, inviting guests to immerse themselves in nature.
Chalet in Stratton
4.96 out of 5 average rating, 137 reviews

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow

MeghaRating, 5 stars2 weeks ago
My girlfriends and I came here for a weekend (Friday night-Sunday morning) just to have a peaceful weekend away and it was delightful! The house was absolutely stunning, had every amenity we could ever need, and was so peaceful. I was so bummed that it rained all weekend (we managed to slip into the hot tub in between rain squalls) because we wanted to utilize all the fun outdoor stuff, but we still had such a good time keeping ourselves entertained inside with how spacious and stocked the house was with games, a fireplace, and a tv in the upstairs living room. Overall it was a very relaxing weekend for us all and we didn’t have to worry about a thing. Also, the little convenience store down the street was so helpful and stocked with plenty of produce that we thought we would have to go to a grocery store for! Definitely recommend going there if you forget any cooking foods you may need, as we were pleasantly surprised. Definitely book if you have the chance - thank you Josh!
Top guest favorite
Chalet in Killington
5 out of 5 average rating, 71 reviews

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

JenniferRating, 5 stars1 month ago
I’ve stayed at this home multiple times, and it’s always a pleasure. The neighborhood is quiet and peaceful, making it a perfect place to relax. The host is incredibly welcoming and makes the entire process smooth and stress-free. The house is always clean, well-maintained, and stocked with everything I need. I always look forward to staying here and would highly recommend it to anyone looking for a comfortable and reliable Airbnb.
Top guest favorite
A comfortable living area is featured, showcasing a cozy sectional sofa adorned with decorative pillows. A round coffee table sits in front, and a large television is mounted above a stone fireplace. Floor-to-ceiling windows offer views of the outdoor landscape.
Chalet in Littleton
5 out of 5 average rating, 54 reviews

Chalet with sunset mountain views

AmrithaRating, 5 stars3 months ago
We had a wonderful time staying here! The house exceeded our expectations and the winter view was spectacular. Chris and Olivia were great, and actively responsive to our messages. Would definitely recommend staying here!

Lakefront chalet rentals

Guest favorite
A spacious room features large floor-to-ceiling windows that provide a view of Lake Sunapee and surrounding trees. The wooden ceiling is designed in a triangular shape, while a comfortable seating area is present in the foreground. A deck with outdoor furniture is visible through the glass doors.
Chalet in Sunapee
4.94 out of 5 average rating, 81 reviews

Lake Sunapee Get Away

LaurieRating, 5 stars1 week ago
Thank you so much for a wonderful stay! The view was spectacular on every level! Lake Sunapee is a very special place, and meant a lot to be able to stay here. Excellent communication and very helpful instructions. The house is well equipped with everything. Beds are so comfortable. Plenty of room to spread out. Quiet and peaceful, loved looking at the lake! Thank you again so much for everything!
Top guest favorite
Private room in Bridgewater
4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

NicolaRating, 5 stars2 months ago
Linda and Ted are very welcoming hosts and have a beautiful home. We had a great weekend and would definitively consider going back.
A wooden dock extends into the calm waters of Lake Rescue, reflecting surrounding trees and distant hills. The serene landscape is framed by greenery, with a clear blue sky overhead. A boat is visible at the edge of the image, alongside a boathouse.
Chalet in Ludlow
4.76 out of 5 average rating, 128 reviews

Charming Lakefront House

EricaRating, 5 stars3 months ago
This home was just what we were looking for. It is charming and spacious, rustic in all of the right ways, with a gorgeous view of the lake, and so close to Okemo. The master bedroom was huge, and we really enjoyed the large communal space with the wood-burning stove. Some of us were cooking while others were playing games, while others were relaxing by the fire, so that we could all easily enjoy each other‘s company. It was the perfect spot for a ski getaway. We all agreed we would love to stay there again.
Guest favorite
A serene lakeside scene showcases a wooden dock extending into clear waters, with several boats anchored nearby. A shaded umbrella rests over a small table, offering a cozy spot for relaxation. Lush green trees line the opposite shore, enhancing the natural setting.
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet on Pristine Beebe Lake

ConnieRating, 5 stars9 months ago
This property was the most peaceful stay I have ever had. So quiet and relaxing. It was the perfect getaway while we were in town for a wedding. The stay had everything we needed to make dinners for the family and a wonderful porch overlooking Lake Beebe. Thanks for sharing your space with my family and me. Side note: Dylan was very successful fishing in this lake and the boats made it easy to explore the lake.

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