Holiday rentals in Winhall

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Top-rated holiday rentals in Winhall

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Guest favourite

Cabin in Londonderry

4.94 out of 5 average rating, 334 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Guest favourite

Home in Winhall

4.95 out of 5 average rating, 122 reviews

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!

Guest favourite

Home in Winhall

4.89 out of 5 average rating, 157 reviews

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.

Guest favourite

Cabin in Londonderry

4.94 out of 5 average rating, 108 reviews

Green Mountain base camp for year-round adventure!

Featured on Levi Kelly's Cabin Tours & Lincoln Car Ad! Deerwood Hill is a 3.6 acre base camp for all Green Mountain adventures. Perfect retreat for all seasons! Within minutes to Stratton, Magic, Bromley, Mt Snow, & Okemo ski resorts! 1 hour to Killington! Under 30 minutes to wonderful Manchester! Let us take care of you in beautiful South Londonderry! ♥Comfortably sleeps 6 ♥2nd Bedroom is open loft with full bath ☒ Booking Guest must be 25. ☒ NO PARTIES, NO SMOKING, NO PETS @deerwoodhill

Guest favourite

Home in Winhall

4.95 out of 5 average rating, 190 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Guest favourite

Cabin in Winhall

4.91 out of 5 average rating, 140 reviews

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!

Guest favourite

Cabin in Jamaica

5 out of 5 average rating, 215 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Guest favourite

Rental unit in Manchester

5 out of 5 average rating, 210 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 571 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Guest favourite

Cabin in Winhall

4.9 out of 5 average rating, 164 reviews

Contemporary 4 bdrm Cabin Hot Tub and Sauna

Our cabin is the ideal Vermont vacation spot, with soaring wood panel rooms, massive brick fireplace in the living room, large wrap around deck, hot tub and sauna. Room for all with four bedrooms, open concept living, dining room, living room, kitchen and lower level family room. The perfect Vermont get away. The cabin is located just minutes from Stratton mountain. We have weekend Shuttle service in our neighborhood to and from the mountain during ski season.

Guest favourite

Cabin in Winhall

4.96 out of 5 average rating, 317 reviews

A-Frame Mountain Retreat near Manchester

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 6 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Guest favourite

Home in Londonderry

4.98 out of 5 average rating, 112 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).