
Vacation rentals in Winhall
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Top-rated vacation rentals in Winhall
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Stone Fence Cabin
Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Log Cabin, King Beds & 7 Min from Stratton Mtn
Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Chic Cabin with Fireplace at Stratton Mountain
Originally built as a corn crib in the 1800s, this 2 bedroom, two bath cabin has been lovingly maintained and features many original details from wide pine floors to a brick fireplace. This beautiful post and beam cabin is nestled in the Green Mountains of Central Vermont with convenient access to some of the best skiing, hiking, & sightseeing: 10 min to Stratton Mountain and Bromley, 15 min to Manchester, 20 min to Magic Mountain, 30 min to Mount Snow, 40 min to Okemo, and 1 hour to Killington

Summit View Ski and Golf Retreat w/hot tub & Sauna
Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

The Mushroom House of Manchester Vermont
Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Snow Valley Cabin-Cozy Escape Near Skiing & Nature
The Snow Valley Cabin is a three bed one-and-a-half bath chalet-style house designed for your perfect Vermont getaway. Wooden vaulted ceilings, wood-burning fireplace, beautiful view of the snow-capped Bromley mountain, and Scandinavian style details. We are conveniently located on the edge of the Green Mountain Forest just 4 miles from Bromley, 9 miles from Stratton, 14 miles from Magic, and 12 minutes to Manchester. Stay here to relax and wind down with friends and family, and even pets!

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.

Holiday Ski Cabin in VT, Hot Tub, Fire Pit, Charm
We can’t wait to host you at Deerwood Hill in Londonderry VT! Featured on Levi Kelly's Cabin Tours! 🌲 Deerwood Hill is a private 3.6 acre private lot 🎿 Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! 📍 Under 30 minutes to wonderful Manchester! ⛰️ 5 miles to Lowell State Park, 8 miles to Appalachian Trailhead ♥Sleeps 6 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

3BR 2BA Stratton Condo w/ Fireplace & Forest Views
Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

Dog Friendly A-Frame Retreat near Hiking, Skiing
Escape to The Vermont A-Frame, our dog-friendly retreat on the edge of Green Mountain National Forest! This cozy 2-bedroom cabin comfortably sleeps 4 and features a stone fireplace, fast WiFi for remote work, and a fire pit. Perfect for a nature retreat, whether you're here to ski, hike, or simply relax, it's your ideal home base for exploring Southern Vermont. Find us on social media! @thevermontaframe
Popular amenities for Winhall vacation rentals
Other great vacation rentals in Winhall

Charming Vermont Schoolhouse

Luxury VT Retreat. Breathtaking Views & Sunsets

Highland Haus: stunning ski getaway with hot tub

Cozy condo w/ pool, hot tub & fireplace

Cedar Hill Lodge | 10 Min to Mt Snow w/Hot Tub

The Nest at Bromley Knolls

Das Skihaus-modern chalet minutes from Stratton

3 Levels w/Spectacular Views: 5 Mins Skiing, Sauna
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ2,024 | ﺩ.ﺇ2,108 | ﺩ.ﺇ1,675 | ﺩ.ﺇ1,260 | ﺩ.ﺇ1,061 | ﺩ.ﺇ1,025 | ﺩ.ﺇ1,124 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,105 | ﺩ.ﺇ1,293 | ﺩ.ﺇ1,399 | ﺩ.ﺇ2,071 |
| 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 |
Frequently Asked Questions
What are the best places to stay in Winhall?
Winhall has cabin rentals, mountain lodges, and family homes, often close to outdoor destinations and ski areas. Staying near the town center or by the woods can provide a peaceful setting with easy access to activities.
What are the best things to do in Winhall with kids?
Families often explore hiking trails, beginner-friendly ski areas, and nature programs suited for young learners. Picnicking by local lakes, wildlife spotting, and visiting nearby farm attractions are also frequently suggested.
What are some of the best things to do in Winhall?
Explore skiing and snowboarding on nearby mountains, hike scenic forest trails, and visit shops featuring Vermont-made goods. Autumn draws visitors for colorful foliage, while local lakes and rivers appeal to those who enjoy fishing or canoeing.
How is the weather in Winhall?
Winhall experiences snowy winters with temperatures between 13–37°F (-11–3°C), while summers are mild and warm, ranging from 52–81°F (11–27°C) with occasional rain. Bring attire for changing conditions, particularly if visiting during transitional seasons.
When is the best time to visit Winhall?
Late spring through early autumn is often recommended for mild weather and vibrant foliage, while winter attracts many for snow sports. The area’s distinct seasons shape outdoor experiences year-round.
What are the best places to visit in Winhall?
Winhall has easy access to ski areas, forest preserves, and rivers suited for outdoor recreation. The town center and nearby villages have inviting shops, local markets, and small art galleries to explore.
What are some hiking trails in Winhall?
Winhall has forest trails suitable for both casual walks and more energetic hikes, often shaded by hardwood trees. Trails around nearby mountains and rivers provide scenic viewpoints and opportunities for wildlife observation.
What are some family activities we can do in Winhall?
Families can enjoy easy forest hikes, hands-on nature exploration, and winter sports during snowy months. Outdoor play areas and small community events around Winhall create welcoming opportunities for visitors of all ages.
What are some of the best day trip ideas from Winhall?
Explore classic Vermont towns with covered bridges and country stores, visit local farms or maple syrup producers, or hike nearby peaks for mountain views. Arts centers, breweries, and regional museums offer engaging experiences around Winhall.
Are there any pet friendly accommodations available in Winhall?
Many vacation rentals in Winhall welcome pets, especially cabins and homes surrounded by nature. Check listings for outdoor spaces like yards or trails nearby, which can make travel enjoyable for you and your pet.
What are some local tips for visiting Winhall?
Layer your clothing for changing mountain weather, and pack comfortable shoes for trails and unpaved paths. Exploring local markets, supporting small businesses, and checking for community events can add to your stay.
What is Winhall known for?
Winhall is known for its mountain scenery, outdoor recreation, and proximity to major ski areas. The town draws visitors looking for seasonal activities, charming local businesses, and scenic autumn foliage.
What are the best hidden gems to explore in Winhall?
Discover quiet forest trails, small lakeside spots ideal for reflection, or tucked-away artisan studios with local crafts. Exploring less-trafficked paths and farm stands around the area provides a deeper look into regional traditions.
What are the best foods to try in Winhall?
Regional favorites often include Vermont cheddar, maple syrup drizzled dishes, and locally inspired comfort food like hearty soups and fresh-baked pies. In nearby spots, you may come across farm-to-table menus featuring seasonal produce and artisanal cheeses.
What should I bring for a trip to Winhall?
Layered clothing is recommended, as Winhall’s temperatures can change quickly throughout the year. Waterproof shoes, warm outerwear in winter, and sunscreen or bug spray for hikes help you enjoy the outdoors comfortably.
What is the nightlife in Winhall like?
Nightlife in Winhall is relaxed, centering on cozy taverns, casual dining spots, and après-ski gatherings near popular resorts. Some venues feature live music or host community events during busy seasons.
What are the most popular events or festivals in Winhall?
Winhall has seasonal festivals often centered around winter sports and autumn foliage. Local celebrations, farmers’ markets, and community gatherings in nearby towns are frequently suggested throughout the year, especially during winter and peak leaf-peeping season.
Are there family friendly vacation rentals in Winhall?
Winhall has a range of family friendly rentals, many with spacious living areas and outdoor spaces for relaxing or playing. Look for homes near mountains or lakes to enjoy easy access to local activities.
Quick stats about vacation rentals in Winhall

Total vacation rentals
Explore 250 vacation rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at ﺩ.ﺇ551 per night before taxes and fees

Verified guest reviews
Over 7,400 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
250 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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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Saratoga Spa State Park
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- National Museum of Racing and Hall of Fame
- Montshire Museum of Science
- Dartmouth College
- Emerald Lake State Park
- Mount Sunapee Resort
- Congress Park




