Vacation rentals in Winhall

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Top-rated vacation rentals in Winhall

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Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 245 reviews

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

Guest favorite
A rustic cabin built on stilts is surrounded by snow-covered ground and tall trees. The structure features a pitched roof and a spacious deck. Sunlight filters through the branches, casting shadows on the snow, highlighting the natural beauty of the winter landscape.
Cabin in Winhall
4.88 out of 5 average rating, 110 reviews

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

Guest favorite
A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.
Home in Winhall
4.95 out of 5 average rating, 172 reviews

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!

Superhost
A welcoming living area features a stone fireplace with a warm fire glowing inside. Wooden beams cross the ceiling, and a red couch is complemented by leather ottomans. A large window reveals a snowy outdoor setting, while a coffee table holds various items.
Home in Winhall
4.86 out of 5 average rating, 202 reviews

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.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 362 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
A serene lakeside scene captures a cozy cabin nestled among lush trees, illuminated by warm light. A dock extends into the water, featuring seating for relaxation. A canoe glides gently across the lake, adding to the tranquil atmosphere of this picturesque setting.
Cabin in Poultney
4.94 out of 5 average rating, 385 reviews

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Guest favorite
A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.
Home in Winhall
4.95 out of 5 average rating, 332 reviews

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

Top guest favorite
An open living area features a high wooden ceiling and large windows, allowing natural light to fill the space. A cozy seating arrangement is complemented by a sculptural centerpiece on a long table, with a fireplace set against a dark brick wall. Two armchairs add to the inviting atmosphere.
Chalet in Winhall
4.98 out of 5 average rating, 128 reviews

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.

Top guest favorite
An elevated deck is softly illuminated by hanging lights, featuring a hot tub and a panoramic barrel sauna. Snow covers the ground, and the landscape is filled with distant hills under a twilight sky, creating a serene outdoor retreat.
Cottage in Shaftsbury
4.98 out of 5 average rating, 760 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Top guest favorite
The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.
Cabin in Newfane
4.99 out of 5 average rating, 309 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Top guest favorite
Cabin in Winhall
4.96 out of 5 average rating, 379 reviews

Dog Friendly A-Frame Retreat near Hiking, Dining

Escape to The Vermont A-Frame, our dog-friendly retreat on the edge of Green Mountain National Forest! This cozy 1965 cabin comfortably sleeps 4 and is perfect for skiers, hikers, or those seeking relaxation. Features a stone fireplace, dedicated workspace with fast WiFi, and a fire pit. Your ideal base for exploring Southern Vermont's natural beauty and charming towns. Find us @thevermontaframe!

Top guest favorite
A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.
Home in Winhall
4.98 out of 5 average rating, 421 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Popular amenities for Winhall vacation rentals

When is the best time to visit Winhall?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$115,270 GYDG$120,081 GYDG$95,396 GYDG$71,756 GYDG$60,459 GYDG$58,367 GYDG$64,016 GYDG$65,271 GYDG$62,970 GYDG$73,639 GYDG$79,706 GYDG$117,989 GYD
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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 240 vacation rentals in Winhall

  • Nightly prices starting at

    Winhall vacation rentals start at G$23,012 GYD per night before taxes and fees

  • Verified guest reviews

    Over 7,840 verified reviews to help you choose

  • Family-friendly vacation rentals

    220 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

    240 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!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall