Holiday rentals in Winhall

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Top-rated holiday rentals in Winhall

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Top guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.94 out of 5 average rating, 122 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Guest favourite
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, 240 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 favourite
A contemporary A-frame house is set against a backdrop of lush greenery. Large windows dominate the facade, reflecting the evening sky. The outdoor seating area is visible, offering a welcoming space for relaxation amidst nature.
Cabin in Jamaica
4.88 out of 5 average rating, 327 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Guest favourite
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
4.89 out of 5 average rating, 107 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 favourite
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, 169 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!

Guest favourite
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
4.94 out of 5 average rating, 323 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

Guest favourite
The cabin is nestled among vibrant autumn foliage, showcasing a blend of orange, yellow, and green leaves. A gravel driveway leads up to the chalet-style house, featuring large windows that invite natural light. Surrounded by trees, the setting offers a serene retreat.
Cabin in Winhall
4.91 out of 5 average rating, 163 reviews

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!

Top guest favourite
An outdoor space is shown with a fire pit surrounded by black Adirondack chairs, set against a snowy landscape. The two-story chalet features large windows and a balcony above. String lights illuminate the exterior, enhancing the inviting winter atmosphere.
Chalet in Winhall
4.98 out of 5 average rating, 124 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 favourite
A charming cabin nestled in a wooded area, showcasing a rustic blue exterior. Large windows illuminate the space, highlighting the inviting porch. Autumn foliage surrounds the home, adding warm colors to the serene landscape.
Cabin in Londonderry
4.95 out of 5 average rating, 172 reviews

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

Top guest favourite
A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.
Home in Winhall
4.97 out of 5 average rating, 151 reviews

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.

Top guest favourite
Cabin in Winhall
4.96 out of 5 average rating, 372 reviews

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

Top guest favourite
A mid-century retreat is illuminated at dusk, surrounded by snow-covered trees. Floor-to-ceiling windows create a warm glow, inviting guests into the living space. The landscape features a serene atmosphere with gently falling snow, enhancing the peaceful setting of the property.
Home in Winhall
4.98 out of 5 average rating, 416 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 holiday rentals

When is the best time to visit Winhall?

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Avg. price£416£433£344£259£218£211£231£236£227£266£288£426
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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 holiday rentals in Winhall

  • Total holiday rentals

    Explore 250 holiday rentals in Winhall

  • Nightly prices starting at

    Winhall holiday rentals start at £113 per night before taxes and fees

  • Verified guest reviews

    Over 7,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    250 of Winhall holiday rentals include wifi 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