House vacation rentals in Winhall

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Top-rated house rentals in Winhall

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Guest favorite

A serene scene features a spacious house nestled beside a tranquil pond. Vibrant autumn foliage enhances the landscape, with a mix of orange, yellow, and green trees lining the property. The grassy area invites exploration, while reflections on the water add to the peaceful ambiance.

Home in Grafton

4.94 out of 5 average rating, 123 reviews

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Superhost

A charming treehouse sits elevated on wooden stilts, surrounded by lush greenery. Soft lighting decorates the deck area, creating a warm environment. A gravel path leads to the entrance, while the tranquil pond reflects the evening sky in the background.

Home in South Londonderry

4.86 out of 5 average rating, 161 reviews

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Guest favorite

A gently sloping field is depicted, bordered by trees with autumn foliage. A red barn and a white building are visible in the distance, set against a bright blue sky with scattered clouds. The landscape conveys a peaceful rural setting.

Home in Townshend

4.97 out of 5 average rating, 121 reviews

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Guest favorite

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

4.94 out of 5 average rating, 144 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!

Superhost

A welcoming living area features a stone fireplace with a warm fire glowing inside. Wooden beams cross the ceiling, and a red couch is complemented by leather ottomans. A large window reveals a snowy outdoor setting, while a coffee table holds various items.

Home in Winhall

4.87 out of 5 average rating, 183 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.

Top guest favorite

A cozy living area features a large sectional sofa adorned with decorative cushions. A wooden coffee table sits in the center, surrounded by an area rug. A stone fireplace with a fire is visible, enhancing the space's comfort, and a staircase leads to the upper level.

Home in Winhall

4.98 out of 5 average rating, 114 reviews

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 tv. Free parking. Two smart TVs & board games. Dining room table converts to a poker table.

Guest favorite

A covered deck features wooden seating accompanied by a small table. Lush greenery surrounds the area, with trees displaying autumn foliage. The view extends towards the Battenkill River and distant hills, creating a serene outdoor setting.

Home in Manchester

4.98 out of 5 average rating, 105 reviews

Private Riverfront Getaway with Mountain Views

Be close to everything Manchester has to offer while enjoying gorgeous views and total privacy in a comfortable home you will have all to yourself! The perfect getaway any time of year. Feels like you are away from it all, but just minutes from amazing hiking, skiing, shopping, dining, and entertainment! 5 minutes to town and Bromley is less than 10 min away. Stratton and Magic Mt are both less than 25 min drives. Hiking trails, kayaking, fly fishing, and more are all right in your backyard.

Top guest favorite

The colonial home features a classic white exterior with black shutters and a welcoming front porch. An American flag is displayed prominently, and soft outdoor lighting highlights the entrance. The well-maintained lawn includes neatly trimmed bushes, creating a warm first impression.

Home in Sandgate

4.99 out of 5 average rating, 117 reviews

Country Colonial Home with rolling fields & stream

This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

Guest favorite

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

Home in Winhall

4.96 out of 5 average rating, 263 reviews

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

Superhost

Home in Jamaica

4.86 out of 5 average rating, 296 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Guest favorite

An interior view showcases a modern staircase with wooden steps and a metal railing, leading to a second floor. Natural light floods the space through large glass windows, illuminating the wooden walls and a stone fireplace. A green plant adds a touch of nature.

Home in Londonderry

4.99 out of 5 average rating, 140 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).

Guest favorite

A dining area is highlighted by a wooden table set for four, surrounded by light green chairs. Natural light fills the space through two large windows, while a vintage hutch displays colorful items against a contrasting gray wall.

Home in Londonderry

4.97 out of 5 average rating, 145 reviews

Wild Blossom Farmhouse - a lovely family getaway

Welcome to Wild Blossom Farmhouse! Conveniently located near Magic, Bromley, Stratton, and Okemo! At our little piece of Vermont, you will find farmhouse-style decor and furnishings, beautiful bright daytime light, and a delightful garden complete with treehouse, tree swing, and fire pit! ***Longterm Stays Allowed*** Four-legged friends welcome with an additional $75 per pet fee.