
Chalet holiday rentals in Woodstock
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Top-rated chalet rentals in Woodstock
Guests agree: these chalets are highly rated for location, cleanliness and more.

Killington Chalet - Hot Tub, Sauna, Boot Dryer
The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

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!

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.

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

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.

The Mountain A-Frame at Mount Snow
Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

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.

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!

Luxe Hot Tub, Sauna 8-12 min Stratton & Mount Snow
Escape to HYGGE HOUSE, a luxurious modern retreat for 8 on four wooded acres in Stratton. Unwind year-in the private HOT TUB and SAUNA or relax in the rustic TREEHOUSE for the ultimate mountain getaway. Just minutes from Stratton Mountain and Mount Snow, this architectural gem is the perfect blend of seclusion and adventure. Features high-speed internet, a gourmet kitchen, and a cozy stone fireplace. Your ultimate cozy & modern mountain getaway awaits.

Scandinavian design Chalet w/ private hiking trail
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.

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.

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.
Popular amenities for chalet rentals in Woodstock
Family-friendly chalet rentals

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!

Private Mountain Sanctuary | 15 Min to Killington

Modern chalet with stream and firepit

Chalet w/ hot tub min. to Stratton & Mount Snow

Okemo Chalet + HOT TUB

Chalet-7 min to Ski Stratton-Woodstove-View-Dog OK

Beautiful Lakeside home Eastman Lake; ski nearby

Mt Snow Chalet: Peaceful Escape w/Hot Tub
Luxury chalet rentals

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Cozy VT Getaway w/ Hot Tub - 10 min to Killington

Ledges Unit: Skyeship Gondola 2 miles w/ HOT TUB

Stratton A-Frame: Hot Tub Sauna EV Boot Warmers

Vintage 70s A frame - Big Hot Tub - 7 min from K1

Minutes to Stratton! Large, private home w. sauna

MountSnow 8 Min, HotTub, GameRoom, FirePit, DogsOk

Stunning Hilltop Getaway- Recreational Paradise
Lakefront chalet rentals

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

Chalet on Pristine Beebe Lake

Lake Sunapee Get Away

MT Retreat / Killington, Woodstock, Rutland, Okemo

Charming Lakefront House
Quick stats about chalet rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at £217 per night before taxes and fees

Verified guest reviews
Over 220 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!
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- Okemo Mountain Resort
- Stratton Mountain
- Squam Lake
- Sugarbush Resort
- Killington Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Montshire Museum of Science
- Mount Sunapee Resort
- Ice Castles
- Squam Lakes Natural Science Center
- Dartmouth College
- Plymouth State University
- Southern Vermont Arts Center
- Stinson Lake




