Family-friendly holiday rentals in Winhall

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

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.

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.

Secluded Luxury Stratton Lodge | Heated Pool

Escape to our 5BR/4.5BA luxury mountain lodge (sleeps 8) featuring panoramic views from every room! Relax in the resort-style backyard with a heated pool, hot tub and seasonally heated pool. Inside, enjoy a gourmet kitchen, cozy fireplace, sauna, an epic game room with pinball, pool, air hockey, darts and more. High-tech and eco-friendly perks include new EV chargers and Sonos speakers throughout the house. With a massive wrap-around deck and fire pit, this is the ultimate private retreat!

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.

Heated Pool, EV Charging, Hot Tub & Barrel Sauna

Experience comfort and convenience at Wandering Moose, a modern retreat perfect for groups of friends and families with older children. Nestled in the serene woods of Winhall, this spacious home features a private heated pool, a stone fireplace, and a large living space. Enjoy easy access to Stratton Mountain's shuttle and nearby outdoor activities year-round. With ample sleeping arrangements and high-speed internet, it's an ideal base for your adventures!

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.

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.

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.