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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

Superhost
An aerial view of the living area and dining space showcases an open layout. A black dining table, surrounded by red chairs, sits against a wall. Adjacent, a sectional sofa with neutral tones faces a coffee table, with light streaming through large windows.
Chalet in Plymouth
4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars4 weeks 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!
Superhost
The exterior of Hideaway Chalet is covered in a thick layer of snow, surrounded by tall trees. The structure features two levels with wooden balconies. In the foreground, a hot tub is visible, partially buried in snow, emphasizing the winter setting.
Chalet in Killington
4.73 out of 5 average rating, 11 reviews

Luxury of large space by ski slopes, deck HOT TUB

SandaRating, 5 stars49 months ago
Our stay at Hideaway was relaxing and exactly how we expected it. The cabin is within a short driving distance from the ski areas and grocery stores, and very comfortable for a family with two children. The host was easy to reach and responded quickly to communication. Overall, a wonderful vacation.
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, 140 reviews

Warm Luxury Mid-Century Modern Chalet

Meg & RobRating, 5 stars2 months ago
Sierra is extremely responsive, understands the ski mentality and very considerate of our group. Thank you so much, we enjoyed spending quality time by the fireplace and of course the super close by Mad River Glen access!!!!!!
Top guest favorite
Chalet in Pittsfield
5 out of 5 average rating, 54 reviews

Mountain Bliss: Spacious Retreat Near Killington

WilliamRating, 5 stars1 month ago
This place is a lovely spot that exceeded expectations for me and my friends! The host was super communicative throughout the whole process, from right after booking through checkout. It’s an amazing place and I would definitely stay here again.
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 stars1 month ago
Great place to stay for okemo mountain!! Very close to local restaurants and the mountain
Superhost
Chalet in Jamaica
4.78 out of 5 average rating, 444 reviews

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

BrennanRating, 5 stars2 days ago
The quiet retreat in Vermont, just like we wanted. We are already comfortable with country living, so being here was easy and peaceful.
Top guest favorite
A cozy den area features a comfortable futon with decorative pillows, accompanied by a small side table and lamp for lighting. The space is anchored by a patterned area rug, while soft natural light enters through a nearby window.
Chalet in Woodstock
4.98 out of 5 average rating, 105 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

VanessaRating, 5 stars1 month ago
Enjoyed everything about our stay. Beautiful property, loved the sauna and ability to snowshoe right out the door. Quaint and nicely decorated. Plenty of privacy, room for guests including extra parking. Had nearly 12 inches of snow while there, quite the winter wonderland. Quickly plowed, shoveled and sanded when needed. Oversized windows and unique architecture made it all extra special. Will definitely return. Perfect for any season.
Guest favorite
A serene ranch-style home is nestled amid a snowy landscape, featuring a combination of dark and light wood siding. The roof is dusted with snow, and the front porch is furnished with rocking chairs. Surrounding trees create a peaceful, wintry setting.
Chalet in Mount Holly
4.92 out of 5 average rating, 60 reviews

3 bedroom mountain getaway

DefneRating, 5 stars1 month ago
My friends and I had a great stay at Daniel’s place! It was very clean with plenty of space to accommodate all of us. We were skiing at Okemo, which was a quick 15 minute drive. Would definitely recommend staying here!

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 weeks 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!
Superhost
The exterior showcases a modern two-story structure with a combination of gray siding and stone accents. A bright red front door is complemented by a wooden ramp leading to a spacious deck. Large windows allow natural light to illuminate the facade.
Chalet in Winhall
5 out of 5 average rating, 9 reviews

4+BR pet-friendly w/ hot tub & Stratton parking!

YairRating, 5 stars2 months ago
Great house, as described. Very responsive host before and during the stay with clear instructions. The couple of things that stood out: 1. Big house; easily sleeps 10, can get a couple more kids in if you want. 2. 15 minutes to Stratton with a parking permit provided which was key. 3. Indoor garage space was great, especially as it was snow storming outside. Kitchen had everything you'd want. Snow was plowed early in the morning. Stayed with wife and 2 teenage daughters and 2 dogs. Would come back. Thank you!
Superhost
A three-story home showcases a steeply pitched roof and multiple wrap-around decks. The light-colored exterior contrasts with the surrounding greenery, while large windows invite natural light. A welcoming wooden front door is framed by steps leading to a manicured lawn and inviting outdoor seating areas.
Chalet in Warren
4.79 out of 5 average rating, 48 reviews

Chalet In The Clouds - MT views, private trails

SamRating, 5 stars1 month ago
Great spot to stay and excellent view of the valley. The main floor is a great space for gathering!
Guest favorite
A dedicated fitness area is equipped with various workout machines, including treadmills and weight benches. Bright red accents on the walls complement the natural light streaming through large windows overlooking a snowy landscape. A stability ball and free weights are also present.
Chalet in Winhall
4.89 out of 5 average rating, 79 reviews

Spacious Chalet W/ Endless Entertainment THE BARN

LuisRating, 5 stars1 month ago
The property was spacious, clean, and well-equipped to accommodate our large group comfortably. Perfect for relaxing after a day on the slopes. The location was ideal, just a couple minutes drive from the ski resort. Bobby, the host, was incredibly responsive and helpful!. We couldn't have asked for a better place for our ski weekend and would highly recommend it to anyone looking for a great group getaway!
Superhost
Chalet in Warren
5 out of 5 average rating, 4 reviews

Scenic Getaway: Unique Large Home with Views!

LouisRating, 5 stars7 months ago
Beautiful place with beautiful view! Close enough to Warren in bike and it was fun to discover the area! House was clean and had everything. The insinkerator switch was closed so we had issues with the sink but other than that, everything was amazing! Jacuzzi water wasn’t clean and had a weird smell, although it didn’t really bother us but it would be great to verify its maintenance!
Guest favorite
A circular fire pit area features multiple wooden chairs arranged around a stone circle, set against a backdrop of a spacious chalet and surrounding greenery. The chalet's large windows provide a view of the outdoor seating area, inviting gatherings.
Chalet in Wardsboro
4.88 out of 5 average rating, 42 reviews

Indoor Hot Tub Chalet | Firepit Fun Near Mt Snow

KellyRating, 5 stars1 month ago
We really enjoyed our stay! The house is beautiful and perfect location for skiing at Mt snow or Stratton. Indoor hot tub was a huge hit & spacious living spaces were great for spending quality time together!
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, 131 reviews

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

TimoRating, 5 stars1 week ago
So hyggelig! Hygge House is 100% what it promises. Wonderful, peaceful place to escape the busy life for a few days and relax in a beautiful house in a beautiful forest. Hot tub, sauna, cosy house, surrounded by nature. Near all activities of Stratton area. We even got five inches of new snow making it winter wonderland in April.
Top guest favorite
A spacious chalet is nestled among colorful autumn foliage, showcasing a large yard. Outdoor seating is arranged near a fire pit, while multiple decks extend from the home, providing inviting spaces to enjoy the natural surroundings.
Chalet in Winhall
4.98 out of 5 average rating, 97 reviews

Mountain view chalet with hot tub & fire pit!

JaymeRating, 5 stars2 weeks ago
Breathtaking views and 5 Star Host! My husband and I wanted to give our son and his friends a remote trip to Vermont. Ryan, our host, was so helpful and went above and beyond to make my son’s 18th birthday “guy’s trip” a success. We truly felt right at home and every single picture looks exactly like the property. Thank you Ryan-you’ve set a high bar.

Lakefront chalet rentals

Guest favorite
A serene waterfront scene is captured, showcasing calm, reflective waters framed by lush greenery. A cozy seating area with striped cushions is positioned nearby, inviting relaxation. In the distance, a family enjoys time on the water while the sun filters through the trees.
Chalet in Antrim
4.94 out of 5 average rating, 96 reviews

Direct Waterfront A-Frame, Close to 3 Ski Areas!

RivkaRating, 5 stars1 week ago
Thank you, was a great stay and an amazing experience with Emily as the host
Guest favorite
A deck with wooden flooring overlooks a serene lake, framed by trees. A charcoal grill is positioned on the deck, ready for use. Various boats are visible on the calm water, enhancing the peaceful lakeside ambiance.
Chalet in Hubbardton
4.94 out of 5 average rating, 96 reviews

Chalet on Pristine Beebe Lake

ConnieRating, 5 stars7 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.
Guest favorite
Chalet in Sunapee
4.94 out of 5 average rating, 80 reviews

Lake Sunapee Get Away

WyattRating, 5 stars2 months ago
Carl was a great host and extremely responsive. He helped make the check in/out process extremely easy and was extremely responsive with any questions. There was snow shovels and salt to deal with snow which was helpful. He helped navigate an issue right away and was very generous with offering help even though he was somewhat unavailable. The house was a great location and very clean, and could accommodate a large group easily. The open floor plan for the kitchen/dining room/living room was very nice and we enjoyed the new range for cooking. Carl even helped to make sure we forgot something that we left at the house after contacting us that it was there! Overall, I would highly recommend staying here.
Top guest favorite
Private room in Bridgewater
4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

NicolaRating, 5 stars1 month 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 serene lakeside view is framed by lush green foliage. A rustic boathouse is positioned near the water's edge, with boats visible alongside it. Various outdoor seating areas are placed on the grassy shore, offering spaces for relaxation amid the natural surroundings.
Chalet in Ludlow
4.76 out of 5 average rating, 128 reviews

Charming Lakefront House

EricaRating, 5 stars2 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.

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