Chalet vacation rentals in Woodstock

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Top-rated chalet rentals in Woodstock

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Guest favorite

A spacious dining area is featured, showcasing a rustic wooden table accompanied by a long bench. A wall mural depicting a vintage aircraft adds character to the space. The adjoining kitchenette is subtly arranged with modern cabinetry and minimalist decor.

Chalet in Fayston

4.97 out of 5 average rating, 166 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

A hallway is visible, featuring warm wooden flooring and a decorative rug. Light enters from a partially open door at the end of the corridor. A small seating area is seen beyond the hallway, creating a cozy and inviting entrance to the open space.

Chalet in Stockbridge

4.84 out of 5 average rating, 159 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.

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, 101 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 neatly arranged bathroom sink area features a polished chrome faucet alongside a small potted plant. A woven basket holds eco-friendly toiletries, with neatly rolled white towels displayed beside it, enhancing the clean and inviting environment.

Chalet in Woodstock

4.98 out of 5 average rating, 105 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

Snow-covered trees frame a distant view of Stratton Mountain, showcasing ski trails etched into its slope. The sky is filled with soft clouds, while the mountain's summit rises against the serene winter landscape.

Chalet in Londonderry

4.94 out of 5 average rating, 114 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 A-Frame chalet is illuminated against a night sky, showcasing its architectural lines and inviting windows. Soft lighting highlights the surrounding greenery, while pathways are visible leading to the entrance. The sloped roof adds to the unique silhouette of the home.

Chalet in Bath

4.93 out of 5 average rating, 207 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.

Guest favorite

A unique living area features a sectional sofa in earthy tones, arranged around a wooden coffee table. Large, custom windows display a backdrop of lush trees, allowing natural light to illuminate the space. A potted plant adds a touch of greenery to the room.

Chalet in Jamaica

4.82 out of 5 average rating, 171 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.

Guest favorite

The exterior of a Scandinavian-style chalet is showcased, featuring a combination of wooden panels and large, square windows. Surrounding greenery enhances the natural setting, while a small deck with seating can be seen at the entrance. A peaked roof adds architectural interest.

Chalet in Royalton

4.94 out of 5 average rating, 174 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.

Guest favorite

The modern kitchen is designed with sleek gray cabinetry and a spacious island featuring four black stools. Spectacular wood beams are visible overhead, complementing the warm tones of the wooden structure. Natural light fills the space through a window above the sink.

Chalet in Franconia

4.95 out of 5 average rating, 300 reviews

Bear Ridge Lodge

Newly built, chalet-style log home featured in both Cabin Living and Log Cabin Homes Magazines. Sweeping mountain and sunset views. Modern, Scandinavian decor. Generous front deck and covered porch for sunbathing, stargazing and outdoor dining in the summer and fall. Soaring stone fireplace makes for a warm, fully-appointed ski lodge in the winter months. 5 minutes from Cannon and 20 minutes from both Loon and Bretton Woods. Miles of National Forest trails out the back door.

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

4.93 out of 5 average rating, 103 reviews

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

My year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s on a small 32-acre pond in New Hampshire. It is truly heaven on earth. There is over 100 feet of direct waterfront. There is a 6 foot main dock, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! Most people catch and release, but please follow NH fishing laws: 16+ needs a license. The property sits on 1/3 of an acre, on a sloped hill.

Guest favorite

A loft bedroom within an A-frame structure displays a spacious bed with a white comforter and decorative pillows. A patterned rug is placed beneath the bed, and large windows frame scenic views. Soft, natural light filters through the space, enhancing the cozy atmosphere.

Chalet in Stoddard

4.95 out of 5 average rating, 263 reviews

Highland Haus AFrame Lake Access Vintage 70s Charm

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Guest favorite

Aerial view of a chalet surrounded by lush green trees, nestled on a hillside. The structure features a rustic design, partially concealed by the abundant foliage, offering a sense of privacy and seclusion amidst the natural landscape.

Chalet in Stockbridge

4.96 out of 5 average rating, 128 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.