Holiday rentals in Winhall

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.

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!

Stratton walk on/ski off, Kings, hot tub, shuttle

Perfect spot for year round relaxation! Located on Stratton Mountain this townhome has everything you could want. • 4 bedrooms • 4 full bathrooms (bathroom on every floor!) • Sleeps 10 across 7 beds (3 King and 2 sets of twin bunks) • 2 living areas • Hot tub • Shuttle • Walk to trails! ~400 yard walk • Ski nearly all the way home! ~50 yard walk • 5 min to Pikes Falls swimming hole • 18 min to Bromley • 25 min to Manchester PLEASE NOTE: Ski on/off is snow/weather dependent!

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.

Stylish Getaway w/ Hot Tub & Firepit Near Stratton

Escape to this stylish Vermont chalet at the end of a quiet street nestled amongst the trees. This 2500 sf home has 5 bedrooms (4 queen rooms, 1 bunk room) and 3 full bathrooms, as well as a grand living room with stone fireplace and separate game room. The Winhall Chalet is centrally located between Stratton, Bromley, and Manchester - less than a 15 minute drive to all. This is the perfect getaway for anyone looking for a beautifully designed home to enjoy with friends and family!

Log Cabin Escape: Clean, cozy & comfortable

Our 5-star log cabin, ranked in the top 1% of homes, is a peaceful retreat for families & friends. Enjoy a wood-burning fireplace, gas grill, and a quiet, wooded setting. Just minutes from skiing and HITS, plus hiking, shops & restaurants. ​ • 3 bedrooms and 2.5 bathrooms • "Spotless" and "well-stocked" guest favorite. ​• Fast WiFi (400+mbps), A/C, and an EV charger. ​• Fireplace with firewood and an outdoor fire pit. ​• Open layout and a finished basement with a rec room.

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 4wd or awd vehicle is recommended. Important note: The grill is put in storage and not accessible November-April due to inclement weather. 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. The house has a non-working fireplace.

Designer Chalet w/ Mountain Views close to it all

Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.

Cozy Getaway! Great Location!

Welcome to Robin's Nest! Come stay in beautiful Vermont. Bromley 5 mins/Stratton 20 mins. Our small 5 bedroom rustic ski cabin is ready for you! 5 mins to Manchester for all amenities. 3 queen, 1 full, and 1 bunk room with 2 bunkbeds. One sitting area with woodstove and TV. Small dining area for 6 off the kitchen and kitchen bar with 4 stools. Large family room with TV. Laundry/mudroom. Deck with BBQ. Yard with firepit. Parking for 4.

4 Bed /3 Bath Mountain Chalet in Stratton, VT

Newly renovated 4 bed / 3 bath chalet tucked away in the Green Mountains just 8 minutes from Stratton, 5 minutes from Bromley, 20 minutes to Magic Mountain and 35 minutes to Okemo. Renovated in September 2022, 4 Peaks Lodge offers guests a comfortable, fresh and quintessential Vermont getaway. Features include brand new appliances, new hardwood and carpet flooring, updated bathrooms, and large outdoor space.

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.