
Chalet vacation 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!

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres
Base rate includes six guests. We welcome events reunions, weddings. Scenic view, nearby lake, golf, hiking! Your private Authentic Chalet is 3600 sq ft on 18 acres. Sleeps 13 (3 bedrooms and full bathrooms, 1 King, 2 Queen, 3 Twin, 2 Queen sleeper-sofas). Summer HVAC, Artisan fireplace, oven, Induction cooktop, air fryer stocked kitchen, ROKU HDTV, fast Wi-Fi, FirePit Patio. Linens/bath towels, soaps-supplied. Optional: A private separate 350 sq ft studio/office. 5-star by work-from-homers.

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.

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.

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 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.

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.

Bromley Aframe - King Master Bed, Wood Fireplace
Classic Aframe home in a private setting but just down the road from Bromley Ski area and downtown Manchester. Primary bedroom has a king bed, fireplace and french doors to backyard. Second bedroom with queen size bed and third lofted bedroom. Full kitchen with Crate and Barrel dishes and drink ware, coffee maker and cookware. Modern bathrooms renovated in 2022. Great place to come with family for a week away. Skiing in winter or hiking in summer, or just relaxing all year round.

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!

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.

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.

Classic A-Frame in Jamaica
This classic A-Frame chalet awaits you and your friends and family, whether you enjoy skiing/snowboarding, hiking, kayaking or just reading in front of a fire. With 2 bedrooms and a loft, galley kitchen and open living area, you can relax and enjoy all that Southern Vermont has to offer. Centrally located to Stratton, Mount Snow, Magic and Bromley ski resorts.
Popular amenities for Woodstock chalet rentals
Family-friendly chalet rentals

Private Brook Chalet: Hot Tub - Fire pit - Ski

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

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

Beautiful Lakeside home Eastman Lake; ski nearby

Designer Chalet w/ Mountain Views close to it all

HotTub, GameRoom, FirePit, DogsOk, 8 Min MountSnow

Cozy & Bright Chalet near Mt Snow ◌ over the moon

Handcrafted Log Chalet (sleeps 2-4)
Luxury chalet rentals

15 Mins to Killington-Secret Speakeasy-Hot Tub

Modern Chalet w/ Hot Tub by Stratton & Mount Snow

OZ- 6BR Ski Chalet Between Killington & Okemo

Spacious Chalet W/ Endless Entertainment THE BARN

Luxe HOT TUB, SAUNA 8-12 min Stratton & Mount Snow

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

Modern Lux Cabin w/ Mtn Views | Fire Pit

Gnome Home Mountain Ski Chalet w/Sauna Killington
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 vacation rentals start at G$62,807 GYD 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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- Squam Lake
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Whaleback Mountain
- Ekwanok Country Club
- Montshire Museum of Science
- Baker Hill Golf Club