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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 stars1 month 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
A private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.
Chalet in Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

MauraRating, 5 stars3 weeks ago
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!
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 stars50 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!!!!!!
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, 445 reviews

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

OscarRating, 5 stars5 days ago
Beautiful place, real quaint and nice to stay at. The surroundings were real nice at nice and the nature was very nice to be surrounded by. All the amenities worked as expected and the beds were comfortable. The porch was our favorite place to relax at; hammock, yard, stereo playing from inside. Great stay … thanks Jason and Sara :))))
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
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars1 month ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
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.

Luxury chalet rentals

Top guest favorite
An inviting outdoor space features a fire pit surrounded by natural stones, with string lights overhead creating a warm glow. The chalet is illuminated from within, showcasing large windows that blend indoor and outdoor environments. A projection screen stands to the left, enhancing the entertaining atmosphere.
Chalet in Mendon
5 out of 5 average rating, 45 reviews

Luxury Chalet Close to Skiing, Golf, and Weddings

KateRating, 5 stars1 week ago
This house was a really special find. It is very thoughtfully designed and feels comfortable and clean. Extra special touches like the record player, shuffleboard, and giant kids' bunk room make it unique. We loved roasting marshmallows at the outdoor fire pit, checking the little creek for frog's eggs, and cooking in the spacious kitchen. Host communication was thorough and easy too. Great find!
Superhost
A bright and inviting living room features high vaulted ceilings and large windows, allowing natural light to fill the space. A stylish fireplace is set against textured walls, while a comfortable sectional sofa is arranged around a round coffee table, creating a cozy gathering area.
Chalet in Dover
4.79 out of 5 average rating, 29 reviews

Chalet 5 mins from MT. Snow w/hottub

JustinRating, 5 stars1 month ago
The place was a perfect ski house and Emilio was very helpful.
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 red Adirondack-style chalet is set against a snowy landscape, featuring a spacious deck with seating. In the foreground, four red adirondack chairs surround a circular fire pit, creating a cozy gathering spot. Tall trees and a blue sky complete the serene setting.
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
An outdoor seating area features four wooden chairs arranged around a fire pit, positioned near a serene pond. Lush greenery and trees surround this tranquil setting, enhancing the peaceful environment. A large rock is visible in the water, contributing to the natural landscape.
Chalet in Warren
5 out of 5 average rating, 4 reviews

Scenic Getaway: Unique Large Home with Views!

LouisRating, 5 stars8 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 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, 132 reviews

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

BethanyRating, 5 stars2 days ago
We adored our stay! It was perfect for our group. The sauna and hot tub were a massive hit. The hosts are wonderful. On a stormy night we lost power and Josh quickly reached out to check-in give us power company updates and let us know the generator would do its thing which it did beautifully. Would love to come back with my family and enjoy further relaxing and peaceful moments together in the mountains!
Top guest favorite
A bright sleeping area features a spacious bed with neutral bedding and two accent pillows. Large windows allow natural light to fill the room, showcasing views of surrounding trees. A modern aqua chair is positioned near the window, complementing the room's wooden beams and ceiling.
Chalet in Killington
4.97 out of 5 average rating, 78 reviews

Chateau Charmaine - Big Hot Tub - No Cleaning Fee

JemilaRating, 5 stars1 week ago
This is a gem of a place in Killington, VT. We were up for some spring riding and hiking, and everything we did was five to 10 minutes away. The place was unique, peaceful, open, great vibes and a yard for our doodles to romp. Between the gear/mudroom entrance and the little touches to make this feel like your own we all wished we had a few more days. If you are able to book this place you will know why this place rocks! Jared was very responsive and eve helped us out with a pack and play when we were in a pinch. 10/10 would recommend this to all outdoor enthusiasts, or just those looking for a Vermont vibe and feel.
Top guest favorite
The open-concept living area features high vaulted ceilings and expansive windows allowing natural light to flood the space. A cozy sectional sofa is situated around a central coffee table, with a gas fireplace nearby. A dining area with a long table sits adjacent to the kitchen.
Chalet in Littleton
5 out of 5 average rating, 54 reviews

Chalet with sunset mountain views

AmrithaRating, 5 stars2 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 serene waterfront view is captured at sunset, showcasing vibrant hues of orange and pink reflected on the calm water. Trees frame the scene, enhancing the connection with nature. A railing is visible, adding a sense of safety and enclosure to the outdoor space.
Chalet in Antrim
4.94 out of 5 average rating, 97 reviews

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

TruthRating, 5 stars2 days ago
The house is exactly as advertised. All the amenities you’d want/need for a little vacation. The hot tub is great
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
A stone fireplace warms a spacious living and dining area, with comfortable seating arranged around a coffee table. Natural light filters through large windows, highlighting elegant decor and a welcoming atmosphere. Nearby, a dining table is set for guests, creating an inviting space for gatherings.
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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