Chalet vacation rentals in Woodstock

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Top-rated chalet rentals in Woodstock

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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, 110 reviews

Prime Killington Proximity | Ski, Sauna, & Soak!

Awarded Airbnb’s "Most Loved Homes!" Escape to our warm chalet, just 5 minutes from the slopes in Killington's most desirable neighborhood. Ski, hike, bike, or golf by day–then unwind in our private sauna, soak in the outdoor hot tub, or curl up by the wood-burning fireplace in front of the TV. Comfy beds, full kitchen, fast WiFi, and billiards & darts in the game room. Close to great restaurants, breweries, nightlife, golf, and breathtaking fall foliage. Your perfect mountain getaway awaits!

Guest favorite

An open loft area features wooden vaulted ceilings and a cozy seating nook with colorful cushions. Two poufs are positioned on a light rug, while a decorative wooden cross is mounted on the wall, adding character to the spacious layout.

Chalet in Fayston

4.97 out of 5 average rating, 171 reviews

4BR Mad River Valley Chalet w/ View, Close to All

*Featured in Food + Wine Magazine!* Welcome to Stars Hollow Chalet, perfect for a romantic getaway, family and friend getaways, or remote work with super-fast internet (rare in the area!). We're on the Fayston/Waitsfield line fantastically close to downtown shops, food, swimming & skiing. Explore all the Mad River Valley has to offer right down the street, then retreat back to the chalet, switch into your slippers and cozy up on our comfy green velvet and leather couches by the fireplace.

Superhost

An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.

Chalet in Stockbridge

4.84 out of 5 average rating, 166 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Guest favorite

A private, heated relaxation pool is surrounded by lush greenery, with clear blue water reflecting the sky. The pool area is framed by a smooth stone border and a wooden fence, offering a sense of privacy and seclusion.

Chalet in Winhall

4.89 out of 5 average rating, 114 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

Superhost

A spacious wooden deck is featured, equipped with a large patio table and six chairs. A hot tub is positioned nearby, surrounded by trees. Large sliding doors offer access to the interior, allowing natural light to fill the space.

Chalet in Killington

4.9 out of 5 average rating, 162 reviews

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Located off East Mountain Road, on a secluded dead end street, just minutes from your choice of the Killington base lodges. There is access to a ski/hiking trail at the end of our street (1/2 mile from the house), and we're surrounded by hiking and biking trails. The house is great for large groups and families, as there are 2 separate living areas (kids like to hang out in the lower family room with large screen TV and games). Very strong and fast internet. Now with AC for summer getaways!

Top guest favorite

An open living area features a high wooden ceiling and large windows, allowing natural light to fill the space. A cozy seating arrangement is complemented by a sculptural centerpiece on a long table, with a fireplace set against a dark brick wall. Two armchairs add to the inviting atmosphere.

Chalet in Winhall

4.98 out of 5 average rating, 108 reviews

Mountain view chalet with hot tub & fire pit!

Welcome to the Vermont View Chalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

Top guest favorite

A modern chalet is situated among lush greenery, featuring a sloped roof and large windows. A cozy outdoor seating area surrounds a fire pit on a grassy lawn, inviting relaxation in a natural setting. A storage area for firewood is visible beside the structure.

Chalet in Woodstock

4.98 out of 5 average rating, 108 reviews

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

Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt

Top guest favorite

A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.

Chalet in Londonderry

4.94 out of 5 average rating, 120 reviews

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Guest favorite

The interior features tall cathedral ceilings with wooden beams and large windows allowing natural light to fill the space. A cozy wood stove provides warmth, while a glimpse of a snowy landscape is visible through the glass doors. Decorative plants add a touch of greenery.

Chalet in Bath

4.91 out of 5 average rating, 221 reviews

Mountain Chalet near a Lake

Enjoy this unique A-Frame Chalet in the coveted Mountain Lakes District of NH just 4 miles outside the White Mountains National Forest. Within 30 minutes to Cannon and Loon Ski Resorts and world famous Franconia Notch State Park, this cozy home gives you all the feels of a mountain lifestyle without giving up any comfort. Sun bathe and barbecue out back on the private decks. Dont foget to relax with a unique nature-surrounded experience in the hot tub! A short walk to a beautiful lake view.

Superhost

A cozy living area is highlighted by striking geometric windows that allow natural light to enter. Dark wood accents complement the light-colored wooden floor. A comfortable sectional sofa and wooden coffee table create an inviting space for relaxation.

Chalet in Jamaica

4.82 out of 5 average rating, 177 reviews

Artists Chalet minutes from Stratton Ski Resort

One of a kind, brand new, hand built by owners in the heart of the Green Mountains. House boasts spacious high ceilings, built with wood from the property and custom windows that reflect the true intention of the h’om’e. Beautiful pikes falls less than one mile down the road. Minutes to Stratton Mountain and Jamaica State Park. Partial mountain view’s! During the winter season, all wheel drive or 4WD is recommended. Pets are welcome on a case by case basis and may be subject to a Pet Fee.

Top guest favorite

The chalet is set against a backdrop of mountains and trees. The property features a large green lawn, and two dogs are seen resting on the grass in the foreground. The warm exterior of the home, complete with a deck, can be seen in the background.

Chalet in Wells

4.98 out of 5 average rating, 103 reviews

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

A beautiful chalet situated between mountains and Lake St Catherine. Whether on the deck or inside the house, you can enjoy the tranquil and serene view of the mountains and the lakes. At over 3000 sq ft, the house offers multiple gathering areas, including separate living room(s), a sociable kitchen, a pool table, and a bar. A perfect home for a retreat. Located less than 10 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

Guest favorite

A cozy living space is highlighted by a modern pink chair positioned near a wood stove, which emits a warm glow. Large glass doors offer views of the wooded surroundings, while a Moroccan rug adds texture to the concrete floor.

Chalet in Royalton

4.93 out of 5 average rating, 180 reviews

Scandinavian design Chalet w/ private hiking trail

* NEW* Starting mid-June, you can conveniently charge your electric vehicle during your stay This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season.