
Family-friendly vacation rentals in Winhall
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Winhall

Total vacation rentals
Explore 220 vacation rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at G$23,014 GYD per night before taxes and fees

Verified guest reviews
Over 7,120 verified reviews to help you choose

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
220 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!
Top-rated family-friendly rentals in Winhall
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Mount Snow Yurt is a one-of-a-kind luxury getaway nestled in the tranquil serenity of Vermont’s mountains, just 7 minutes from the Mount Snow Ski Resort, an Epic Pass destination. This magnificent pet-friendly yurt is surrounded by the captivating scenery of Mount Snow and is located near a beautiful creek, providing an even more peaceful and serene atmosphere. Furnished with modern amenities, including a luxurious private sauna, this yurt offers everything you need for a relaxing stay in nature

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

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

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!

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.

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.

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.

Modern Cabin with Outdoor Spa on Vermont Farm
Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

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.
Popular amenities for Winhall family-friendly rentals
Family-friendly home rentals with a hot tub

Log Cabin: Amazing Views, River Frontage, Hot Tub

The Birchwood Cabin - Stunning Mountain Views

Romantic Ski Cabin in VT, Hot Tub, Fire Pit, Charm

Luxe Hot Tub, Sauna 8-12 min Stratton & Mount Snow

Mountain side acres

Vermont Mirror House

Glamping Cabin with Hot Tub on Flower Farm

Vermont Getaway Apartment
Family- and pet-friendly home rentals

Little Red House Vermont

Rustic Cabin in foothills of Green Mountains

The Post Haus: one-of-a-kind modern VT experience

Classic Vermont A-Frame | Fire Pit | Near Stratton

Log Cabin King Beds AC Near Hike Bike Swim Golf!

Apple Blossom Cottage: A Tiny House

Designer Chalet w/ Mountain Views close to it all

The Rafters Lodge
Family-friendly home rentals with a pool

Adams Farm-"The Little Farmhouse"

~10% OFF~Walk To Mountain~Amenities

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

Moon Valley Country Retreat no clean fee pets yes

Dream Catcher Farm

Cozy cottage with pool, walking distance to lake

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$140,388 GYD | G$151,896 GYD | G$109,633 GYD | G$83,689 GYD | G$73,228 GYD | G$71,763 GYD | G$72,391 GYD | G$74,274 GYD | G$68,625 GYD | G$82,434 GYD | G$83,689 GYD | G$133,693 GYD |
| 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 |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Québec City Vacation rentals
- Newark Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Providence Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- Rentals with outdoor seating Winhall
- Rentals with a hot tub Winhall
- Rentals with an EV charger Winhall
- Rentals with a sauna Winhall
- Fitness-friendly rentals Winhall
- Rentals with a patio Winhall
- Condo rentals Winhall
- Rentals with lake access Winhall
- Rentals with a fire pit Winhall
- Pet-friendly rentals Winhall
- House rentals Winhall
- Cabin rentals Winhall
- Chalet rentals Winhall
- Apartment rentals Winhall
- Rentals with a washer and dryer Winhall
- Ski-in/ski-out rentals Winhall
- Rentals with a fireplace Winhall
- Townhouse rentals Winhall
- Rentals with pools Winhall
- Family-friendly rentals Bennington County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Killington Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Dartmouth College
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Rensselaer Polytechnic Institute
- Bromley Mountain Ski Resort
- Saratoga Spa State Park
- Montshire Museum of Science
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Emerald Lake State Park





