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Chalet vacation rentals in Woodstock

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Popular amenities for Woodstock chalet rentals

Family-friendly chalet rentals

Guest favorite
The chalet features a wooden exterior with a green roof, set amid snow-covered ground. A large deck with wooden railings extends from the front, offering space for outdoor seating. A gentle sloping staircase leads to the entrance, framed by evergreen trees.
Chalet in Mount Holly
4.97 out of 5 average rating, 152 reviews

Charming Summit View Chalet near Okemo and Lakes

LynnRating, 5 stars4 months ago
We enjoyed our stay at the Chalet in Mt Holly. It was our first time not using a Ski In/Ski Out and we were not sure how we would like it. The location was private and the surrounding were so beautiful and peaceful. Libby was very responsive and easy to work with. The home itself was comfortable and clean. We would definitely consider staying here again.
Guest favorite
A spacious living area features vaulted wooden ceilings with exposed beams, allowing natural light to fill the room. Comfortable couches are arranged around a central coffee table, with a large television set against the wall. Light-colored curtains frame the windows, enhancing the inviting ambiance.
Chalet in Killington
4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

ScottRating, 5 stars3 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
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, 129 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars1 month 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.
Superhost
Chalet in Jamaica
4.86 out of 5 average rating, 94 reviews

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

DanielRating, 5 stars3 months ago
Our stay was fantastic. The house was conveniently located relative to Stratton mountain, very comfortable, and the host was fantastic
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.
Superhost
Chalet in Warren
4.79 out of 5 average rating, 48 reviews

Chalet In The Clouds: Your Pure Vermont Escape

SamRating, 5 stars3 months ago
Great spot to stay and excellent view of the valley. The main floor is a great space for gathering!
Guest favorite
A cozy chalet is nestled among tall trees, with a fire pit surrounded by seating. The exterior showcases a mix of wood and green materials, and a balcony extends from the upper level. Sunlight filters through the leaves, creating a serene outdoor setting.
Chalet in Mendon
4.96 out of 5 average rating, 26 reviews

Pico/ Killington chalet, minutes to the mountain

MelissaRating, 5 stars4 months ago
The home was the perfect getaway for a weekend of snowboarding. Enough space for everyone to have their own area but also cozy enough to be all together, perfect mix of both. Absolutely would recommend to anyone looking to be close to the mountain and all the other amenities the Killington/Pico area has to offer.
Superhost
Chalet in Warren
5 out of 5 average rating, 4 reviews

Scenic Getaway: Unique Large Home with Views!

LouisRating, 5 stars9 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!
Top guest favorite
Chalet in Killington
4.99 out of 5 average rating, 70 reviews

The Overlook - AC | Hot Tub | View | Fires | Games

KevinRating, 5 stars1 month ago
Oh my God the views! Super cute place with plenty of room and awesome hosts. The hot tub is nice (but SUPER chlorinated, which was a little annoying, but I get it). The kitchen is STOCKED with gadgets and cookware, which is super convenient. Also, killer location: great restaurants less than a mile away in Killington village and Rutland only 20 min away. Everything was clean and tidy and the whole family had an absolute blast. Will definitely come back.
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 stars4 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!
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
4.98 out of 5 average rating, 80 reviews

Chateau Charmaine - Big Hot Tub - No Cleaning Fee

WillRating, 5 stars3 weeks ago
Of all the places I've stayed, this is the best one by far. This house is very unique, spacious and relaxing and exceeded all of our expectations. This house has a record player with cool records. Does anything more need to be said after that?!? Well, yes! There is a fire ring behind the house, the house is in a very peaceful setting and the hot tub is amazing, the furniture and beds are clean and comfortable, the kitchen had everything you could possibly ever want and . . . this is the most cozy house ever, with individual thermostats for each room and each bathroom too, plus a nice and blazing pellet stove in the living room which is super easy to use. Whoever designed and built this place was a true master of space. And the hosts were the most responsive and kind - hats off to hosts Jared & Corey for such a great place! We will be back someday.

Lakefront chalet rentals

Guest favorite
A charming A-frame cabin is surrounded by tall evergreen trees, with a wooden deck accessible by stairs leading to the entrance. Snow blankets the ground, and large windows provide a view of the interior, creating a cozy, inviting exterior impression.
Chalet in Sunapee
4.94 out of 5 average rating, 81 reviews

Lake Sunapee Get Away

LaurieRating, 5 stars2 weeks 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 stars3 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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