
Holiday rentals in Winhall
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Top-rated holiday rentals in Winhall
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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 AC Near Hike Bike Swim Golf!
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

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

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 Hygge Loft- mid-mod cabin on 70 forested acres
The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Designer Chalet w/ Mountain Views close to it all
A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

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!

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.

Stratton Chalet | Barrel Sauna, Hot Tub & Views
Escape to Stratton Chalet, 5 mins from a pristine swimming pond, featuring a new hot tub and barrel sauna with incredible Stratton mountain views. Recently renovated, Stratton Chalet features a large stone fireplace, outdoor, modern fire-pit area, two outdoor decks, contemporary outdoor furniture, Bose soundbar, and a well-equipped kitchen.

Modern Cabin ~ 3min to Stratton Resort
Enjoy your stay in this secluded mountain cabin a 3 minute drive to Stratton resort. The cabin offers a lovely space to unwind and relax after a day on the slopes. Hosts are happy to provide local guidance for skiing, shopping, and food. Situated amongst 45 private acres.
Popular amenities for Winhall holiday rentals
Other great holiday rentals in Winhall

Stratton Summer House | Trails + Swim Holes + AC

Highland Haus: stunning ski getaway with hot tub

Brewster's Hollow

Little Pond Homestead 4 miles to Stratton!

Stylish Getaway w/ Hot Tub & Firepit Near Stratton

The Nest at Bromley Knolls

Summer Get-A-Way! Sleeps 8! Game Room & Deck

Alpine Reflection + Hot Tub
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £455 | £460 | £331 | £257 | £216 | £209 | £229 | £233 | £225 | £263 | £285 | £422 |
| 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 holiday rentals in Winhall

Total holiday rentals
Explore 240 holiday rentals in Winhall

Nightly prices starting at
Winhall holiday rentals start at £82 per night before taxes and fees

Verified guest reviews
Over 7,840 verified reviews to help you choose

Family-friendly holiday rentals
220 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
240 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!
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Killington Resort
- Dartmouth College
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- National Museum of Racing and Hall of Fame
- Montshire Museum of Science
- Mount Sunapee Resort
- Rensselaer Polytechnic Institute
- Emerald Lake State Park





