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Chalet vacation rentals in Woodstock

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Quick stats about chalet rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at $422 CAD per night before taxes and fees

  • Verified guest reviews

    Over 240 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodstock rentals

  • 5 Average rating

    Woodstock stays are highly rated by guests—averaging 5 out of 5!

Top-rated chalet rentals in Woodstock

Guests agree: these chalets are highly rated for location, cleanliness, and more.

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Guest favourite
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

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.

4.86 out of 5 average rating, 210 reviews
Top guest favourite
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

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

4.98 out of 5 average rating, 120 reviews
Top guest favourite
An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.
Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

4.99 out of 5 average rating, 112 reviews
Top guest favourite
The chalet is positioned on a gently sloping grassy area, featuring a spacious deck with a hot tub and several outdoor seating options arranged around a fire pit. Large windows reflect warm interior light, framing a serene natural backdrop of trees, enhancing the inviting ambiance.
Chalet in Winhall

Mountain view chalet with hot tub & fire pit!

Welcome to the @vermontviewchalet! 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.

4.99 out of 5 average rating, 140 reviews
Top guest favourite
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

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!

4.95 out of 5 average rating, 128 reviews
Top guest favourite
Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

4.97 out of 5 average rating, 112 reviews
Guest favourite
A cozy indoor relaxation area features a large hot tub alongside natural wood paneling. Rattan chairs and lounge chairs surround a geometric-patterned rug. Greenery is present, enhancing the tranquil setting. Natural light enters through the window, creating a warm atmosphere.
Chalet in Killington

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

NEW! BearHaus is a fully renovated 6 bedroom Killington chalet that is conveniently located in the heart of town in a tranquil forest setting. The Chalet is built in the classic Austrian style and lovingly renovated top to bottom with brand new modern amenities. There are two kitchens, a giant table for 16 people, one of the biggest hot tubs in all of Killington, a beautiful wet bar with wine fridge and plenty of room for everyone to spread out or hang out together.

4.96 out of 5 average rating, 114 reviews
Guest favourite
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

Scandinavian design Chalet hiking trail + hot tub

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. Goodland wood burning hot tub is available 365 days a year.

4.94 out of 5 average rating, 228 reviews
Top guest favourite
A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.
Chalet in Stockbridge

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.

4.97 out of 5 average rating, 165 reviews
Guest favourite
A warm living space is crafted with wooden paneling and large windows that provide natural light. Comfortable seating includes a leather sofa and patterned armchairs, arranged around a wooden coffee table. Soft lighting is provided by lamps, enhancing the cozy atmosphere.
Chalet in Killington

Large Chalet; Sauna, Hot Tub; Walk to Trail

Short walk (200 yds) to Homestretch ski trail at Killington ski mountain. Trail is weather dependent, from late Dec to mid-March. If the nearby trail is not open, it will not be available. Close to hiking/biking trails, golf, nightlife, rivers and lakes. Large open living space and lots of sleeping space makes our home comfortable for large groups. Driveway holds up to 5 cars. Enjoy relaxing in the hot tub, sauna or spending time by the fire.

4.86 out of 5 average rating, 265 reviews
Top guest favourite
The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica

Designer Chalet w/ Mountain Views close to it all

Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.

4.98 out of 5 average rating, 113 reviews
Guest favourite
Chalet in Jamaica

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

4.97 out of 5 average rating, 295 reviews

Popular amenities for Woodstock chalet rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly chalet rentals

Top guest favourite
The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.
Chalet in Wilmington

Snug Chalet - Wi-Fi + Close to Mount Snow

4.97 out of 5 average rating, 148 reviews
Superhost
The A-Frame chalet is set amidst vibrant autumn foliage, showcasing a wrap-around deck with wooden railings. A balcony extends above, offering a view of the surrounding trees and an inviting outdoor space with seating.
Chalet in Dover

The Mountain A-Frame at Mount Snow

4.86 out of 5 average rating, 319 reviews
Guest favourite
Chalet in Killington

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer

4.84 out of 5 average rating, 264 reviews
Guest favourite
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

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

4.89 out of 5 average rating, 180 reviews
Top guest favourite
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

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

4.98 out of 5 average rating, 125 reviews
Superhost
The kitchen features a modern design with stainless steel appliances and granite countertops. A round white dining table is placed at the center, surrounded by four white chairs. An antler chandelier hangs from the ceiling, complementing the exposed wooden beams.
Chalet in Newbury

**Remodeled** Chalet near Beach and Mt. Sunapee

4.83 out of 5 average rating, 288 reviews
Guest favourite
A cozy living area is highlighted by a mix of large windows allowing natural light to fill the space. Two sofas, one in dark fabric and the other in teal, face a wooden media console with a television. A patterned area rug anchors the seating arrangement.
Chalet in Dover

Cozy & Bright Chalet near Mt Snow ◌ over the moon

4.89 out of 5 average rating, 215 reviews
Top guest favourite
Chalet in Wardsboro

Shiny Elk Chalet - near Mt Snow w/ cozy fireplace

4.98 out of 5 average rating, 114 reviews

Luxury chalet rentals

Top guest favourite
The exterior of a modern home is framed by lush greenery, featuring a dark wooden structure with large windows. A front entrance is highlighted by wooden steps leading to the door, while a gravel path borders the property.
Chalet in Winhall

Minutes to Stratton! Large, private home w. sauna

4.96 out of 5 average rating, 104 reviews
Top guest favourite
The exterior of Hygge House is highlighted by sleek wooden siding and a modern design. Large windows reflect the surrounding greenery, while a stone pathway leads to the entrance. Sunlight filters through the trees, illuminating the inviting facade set on a spacious grassy area.
Chalet in Stratton

Luxe HotTub, Sauna, Fall Leaves, Stratton /Mt Snow

4.96 out of 5 average rating, 175 reviews
Guest favourite
Chalet in Winhall

4BR Ski Chalet | Hot Tub | Mins to Stratton, VT

4.89 out of 5 average rating, 135 reviews
Guest favourite
The great room features tall cathedral ceilings and large windows allowing natural light to fill the space. A mix of seating options, including leather chairs and a sectional sofa, surrounds a wooden coffee table. A colorful area rug adds warmth, complementing the woodwork throughout.
Chalet in Dover

Brookside Chalet w/ Hot Tub for Fall Foliage

4.9 out of 5 average rating, 102 reviews
Guest favourite
Chalet in Stockbridge

Private Mountain Sanctuary | 15 Min to Killington

4.92 out of 5 average rating, 51 reviews
Guest favourite
Chalet in Killington

Spacious modern chalet designed for après-ski

5.0 out of 5 average rating, 9 reviews
Top guest favourite
Chalet in Jamaica

Stratton Ski Haus | Sleeps10, Hot Tub, Sauna, EV

5.0 out of 5 average rating, 34 reviews
Guest favourite
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

Okemo Chalet + HOT TUB

4.84 out of 5 average rating, 94 reviews

Lakefront chalet rentals

Superhost
An A-Frame cabin is set on a sloped hill, surrounded by trees. The cabin features a deck overlooking the water, with kayaks and a hammock visible on the lawn. A wooden dock extends into the pond, enhancing the serene outdoor setting.
Chalet in Antrim

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

4.89 out of 5 average rating, 159 reviews
Guest favourite
Chalet in Fairlee

Idle Pine Lakefront Retreat | Bogart’s VT Getaway

5.0 out of 5 average rating, 8 reviews
Guest favourite
A serene lakeside view features a wooden dock extending into calm waters, accompanied by two Adirondack chairs. Lush greenery surrounds the scene, while a fire pit with rocks is positioned on the shore. Several boats are visible along the water's edge.
Chalet in Ludlow

Charming Lakefront House

4.77 out of 5 average rating, 139 reviews
Guest favourite
A spacious lawn area is visible in front of the chalet, featuring lounge chairs arranged along the grassy expanse. The chalet's deck overlooks the yard, with steps leading down from the outdoor seating area. Surrounding trees provide a natural backdrop.
Chalet in Hubbardton

Chalet on Pristine Beebe Lake

4.94 out of 5 average rating, 101 reviews
Top guest favourite
The lakefront home features an A-frame structure with large windows that provide ample natural light. A wide deck extends from the main level, overlooking the surrounding trees. A staircase leads down to the ground level, where seating is arranged to enjoy the peaceful outdoor setting.
Chalet in Sunapee

Lake Sunapee Get Away

4.94 out of 5 average rating, 86 reviews
Top guest favourite
A spacious house sits nestled among trees, showcasing large windows that provide ample natural light. A deck with an umbrella overlooks a well-maintained lawn. The scene is set against a backdrop of colorful foliage and a sky painted with soft clouds.
Private room in Bridgewater

MT Retreat / Killington, Woodstock, Rutland, Okemo

4.99 out of 5 average rating, 183 reviews

Destinations to explore