
Chalet holiday rentals in Woodstock
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Woodstock holiday rentals start at €263 per night before taxes and fees

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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.

BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Welcome to Bear-varia! A Bavarian themed chalet in the heart of Killington. Close to everything with a great location off the access road by the market. Perfect for friends and families with plenty of space to spread out. Inside there's a fireplace, TV with Roku and fast internet. Also, an area for gaming with a second TV with Nintendo, a PacMan arcade game and plenty of board games to make memories and connect. Outside, there is a large yard and outdoor dining, fire pit and frisbee golf!

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

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!

Direct Waterfront A-Frame, Close to 3 Ski Areas!
My direct waterfront, year-round A-Frame cabin is 30 min to Mount Sunapee, 20 min to Crotched, and 15 min to Pat's Peak! It’s located on a small 32-acre pond near Franklin Pierce Lake with over 100 feet of waterfront. There is a 6 foot main dock to load kayaks, and a small fishing dock off to the side. The fishing on our pond gets rave reviews! The property sits on 1/3 of an acre, on a sloped hill. It's located between Keene and Concord, and nearby many great hiking and snowmobile trails

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!

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

Warm Luxury Mid-Century Modern Chalet
Woodward Haus is a stylish MCM retreat with wood, glass, & stone design. Perfect for remote work, a romantic weekend, a multifamily gathering, a girls' weekend, or retreat. MRV offers all season fun: farmer's market, swimholes, farms, hiking, road & mtn bike, golf, climbing, tubes on the river and lake, can't be beat. The house is nestled in the woods w/ beautiful views mountains. The area's food & breweries, including Lawsons are phenomenal. 1 min to MRG & 14 min to Sugarbush. Exp Wifi

Designer Chalet w/ Mountain Views close to it all
A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

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.

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

Brook Haven Retreat - Minutes to Mt Snow&Stratton

Mount Sunapee Chalet

The Skihaus - modern chalet minutes from Stratton

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

Highland Haus | Cozy 70s Aframe | Lake Access

Snug Chalet - Wi-Fi + Close to Mount Snow

HYGGE HOUSE Luxe HotTub, Sauna, Summer/Fall Leaves

Mountain Lakes. Pet friendly. Entire Chalet.
Luxury chalet rentals

Ledges Unit: Skyeship Gondola 2 miles w/ HOT TUB

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Minutes to Stratton! Large, private home w. sauna

Maple Pine w/Hot Tub Pool Table 3min to Mount Snow

Spacious 5BR Chalet | 2 Min to Mountain

Chalet | Heated Pool + Hot Tub | near Stratton, VT

Private Mountain Sanctuary | 15 Min to Killington

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

Charming Lakefront House

Chalet on Pristine Beebe Lake

Lake Sunapee Get Away

MT Retreat / Killington, Woodstock, Rutland, Okemo
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- Chalet rentals Windsor County
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- Okemo Mountain Resort
- Squam Lake
- Stratton Mountain
- Sugarbush Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Killington Resort
- Middlebury College
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Squam Lakes Natural Science Center
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Ice Castles
- Stinson Lake
- Camp Plymouth State Park





