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

Snug Chalet - Wi-Fi + Close to Mount Snow
This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!
Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back & enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled 2023! Open floor plan w/wood burning fireplace. Main bedroom has new King Bed & twin bunks. Finished basement with new Queen size bed & twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property.

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit
7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

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.

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.

Private Brook Chalet: Hot Tub - Fire pit - Ski
The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

Serene & Stylet Chalet•HOT TUB•Skiing•Manchester
Hey there, relaxation enthusiasts and adventure seekers alike! Shady Pines Chalet is your spot: a groovy 4-bed/2-bath cabin tucked away in the lush, serene embrace of the Green Mountains! It's just 15mins from Manchester, where you can shop and dine like a pro. Plus, you're in prime adventure territory: hiking, kayaking, & fly-fishing are all on the menu. And if you're a winter warrior, Bromley (25min) and Stratton & Magic Mountains (40min) are ready for your skiing prowess!!

Luxe Hot Tub, Sauna 8-12 min Stratton & Mount Snow
Welcome to HYGGE HOUSE, a luxurious modern retreat on 4 wooded acres in Stratton. Inspired by the Danish concept of hygge, this home embodies warmth, coziness, and well-being. Unwind year-round in a private HOT TUB, SAUNA, and even a TREEHOUSE for the ultimate mountain getaway. Just minutes from Stratton and Mount Snow resorts, this architectural gem is a haven for relaxation and adventure, with an open floor plan, cozy fireplace, and large windows connecting you to nature.

MountSnow 8 Min, HotTub, GameRoom, FirePit, DogsOk
✔ Relax in the Hot Tub under the Pergola & String Lights ✔ Cozy Fire Pit Area with Adirondack Chairs ✔ Fun Game Room with Air Hockey & Connect Four ✔ 4 Bedrooms, 3 Bathrooms ✔ Dog-Friendly (w/ fee) ✔ 8 Minutes to Mount Snow, 30 minutes to Stratton, 60 minutes to Okemo ✔ 20 minutes to Lake Whitingham/Harriman Reservoir for boating & fishing ✔ Fast Wi-Fi for Remote Work & Streaming ✔ High Chair & Pack N' Play Provided ✔ All Linens, Towels, & Soaps Included
Popular amenities for Winhall chalet rentals
Family-friendly chalet rentals

Classic A-Frame in Jamaica

The Lodge on Warner Hill

Peaceful Chalet In Londonderry

Shiny Elk Chalet - near Mt Snow w/ cozy fireplace

Large Chalet; Sauna, Hot Tub; Walk to Trail

The Skihaus - modern chalet minutes from Stratton

Family Fun, Ski/ Snowboard 10 min to Stratton

Mt Snow Retreat | Walk to brewery
Luxury chalet rentals

On Shuttle, Sleeps 10, 4 Bathrooms, Full Kitchen

Spacious Chalet W/ Endless Entertainment THE BARN

Modern Lux Cabin w/ Mtn Views | Fire Pit

Mt Snow Chalet: Peaceful Escape w/Hot Tub

The Great Escape!

Wine Moose Hot tub Fireplace Sauna 9min to Mt Snow

Cozy Chalet near Okemo Jacuzzi/Sauna

Luxurious Fireside Lodge w/Stratton View
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R10,716 ZAR | R10,963 ZAR | R7,831 ZAR | R6,595 ZAR | R6,496 ZAR | R6,067 ZAR | R5,770 ZAR | R6,595 ZAR | R4,732 ZAR | R6,595 ZAR | R5,704 ZAR | R9,842 ZAR |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about chalet rentals in Winhall

Total vacation rentals
Explore 30 vacation rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at R1,813 ZAR per night before taxes and fees

Verified guest reviews
Over 1,420 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Winhall vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winhall rentals

4.9 Average rating
Winhall stays are highly rated by guests—averaging 4.9 out of 5!
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- Chalet rentals Bennington County
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- Chalet rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
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- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Lake George Expedition Park
- Whaleback Mountain
- Hildene, The Lincoln Family Home
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- National Museum of Racing and Hall of Fame




