Family-friendly holiday rentals in Winhall

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

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.

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

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.

Shred Shack: A/C | Hot Tub | Sauna | EV charger

Escape to the Shred Shack by 42 North LP, your ultimate mountain escape in Vermont! The Shred Shack offers stunning mountain & valley views from its expansive great room. Relax & recharge by the grand fireplace, in the private indoor sauna, or the mountain-view hot tub. Entertain effortlessly in the open-concept kitchen, dining, and living area – perfect for memorable meals & gatherings. Kids will love the unique indoor swing! Your perfect blend of adventure and comfort awaits!

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

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!

Minutes to Stratton! Large, private home w. sauna

Your dream ski vacation awaits! Less than 2 miles to Stratton Mountain access road; 15 minutes to Bromley; 15 min to Manchester Ctr; 30 min to Mt Snow. With three levels, your group can really spread out: 4 bedrooms + bonus room, 4 full baths, open kitchen, living room with a fireplace, loft area, sauna, and laundry. Monthly discount available. Ski Shuttle for rentals of 30+ days.

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.