Ski-in/Ski-out holiday rentals in Jay

4.97 out of 5 average rating, 131 reviews

A large house featuring a blend of stone and timber architecture is set against a backdrop of lush greenery. The exterior showcases a prominent gable roof, large windows, and a welcoming porch. A separate structure with a barn-like design is visible in the background.

Home in Stowe

Cozy Mountain Home w/Million $ View

Privacy, awesome views of Trapp Family Lodge and Stowe Mountain Resort. 5 min drive to town and 10 min to ski area. Home to famous visiting musicians thru the years including the recording of Phish's " Story of the Ghost ". Family or a group love it! My home offers a great open space to relax in front of the fire and enjoy the company of friends and/or family. It easily accommodates a lot of people. The entire house is for rent although less is open for discussion as well, just ask. I stay in an apartment next door so am readily available should anyone have a question. In the winter it is best to have snow tires or four wheel drive to access the property. I am around however to assist if you need help getting up the hill. The road and driveway are both maintained very well but this is Vermont and we get a lot of snow!

4.9 out of 5 average rating, 303 reviews

The exterior of the cabin features a vibrant red door adorned with a wreath, complemented by large windows allowing natural light. A wood storage area is seen to the side, filled with neatly stacked logs. Snow covers the ground, surrounded by trees for added privacy.

Home in Craftsbury

Waterfront cabin

This one bedroom waterfront guest cabin is located on Great Hosmer Pond in the beautiful town of Craftsbury Common, Vermont. The ownerof the property live in the main house. The cabin has access to the cross country ski trails of the Craftsbury Outdoor Center. Swimming dock on property with access to kayaks. The cabin is made of double tongue and grooved red western cedar. The cabin is available year round except for 'mud season'. Please take note that this is a rustic cabin and not a hotel.

4.97 out of 5 average rating, 251 reviews

Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.

Barn in Morristown

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

4.95 out of 5 average rating, 108 reviews

A comfortable lounge area features light gray seating and a small white table beside a potted plant. A cozy rug covers the floor, and natural light enters through large windows, illuminating the open space. Decorative items including a mirror and a hanging blanket are subtly integrated into the design.

Tiny home in Brome

Petit loft mezzanine style barn *Air conditioner*

Ce magnifique petit loft privé et exclusif, saura vous charmer par son cachet de style barn, sa mezzanine unique, son balcon avant et arrière, pour contempler la campagne de Brome. Par sa localisation parfaite pour pratiquer une diversité de sports, à proximité des stations de skis de Bromont(15 min), de Sutton(12 min) et 5 min du Lac Brome, entouré des plus belles routes de la region pour le cyclisme. Valley House, est un petit nid douillet, pour un weekend en amoureux.. Vous serez charmé !

Luxe

A spacious chalet is surrounded by tall trees and lush greenery. A multi-level deck with red outdoor seating enhances the inviting outdoor space. A well-maintained garden features a stone border and a variety of plants, creating a serene setting.

Chalet in Potton

HAVRE DE PAIX lac-Golf-Tennis-Ski Mont Owl's Head

Résidence luxueuse, chaleureuse et conviviale pouvant accueillir jusqu'à 12 pers. situé dans les cantons de l'est, sur le Mont Owl's Head, sur les pistes de ski, accessible à pied au lac, au tennis et à 5 min. du golf. Tout vous charmera ! Elle fût entièrement rénovée et décorée avec soin, et ce, sans oublier un détail pour votre confort. Vous serez au cœur des activités sportives et de plein air, tout y est ! Ski, raquette, golf, vélo, plage, tennis, randonnée. C'est un havre de paix !

4.99 out of 5 average rating, 136 reviews

4.98 out of 5 average rating, 173 reviews

A circular fire pit is surrounded by three rustic wooden benches, positioned on a grassy area among lush trees. Two adults and a child sit comfortably, enjoying the warm glow of the fire. Behind them, the unique treehouse structure, with large windows, blends into the natural setting.

Treehouse in Moretown

4-Season Treehouse @ Bliss Ridge; Best Views in VT

Insulated, thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Fabulous “Jotul” fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works! No pets.

4.93 out of 5 average rating, 123 reviews

The exterior of the condominium features a blend of grey and green siding, accented by vibrant red doors. A well-maintained landscape includes shrubs and ornamental plants surrounding the entrance. The pitched roof and decorative gables create an inviting architectural design against a backdrop of lush trees.

Townhouse in Jay

Ski In Ski Out in style on Village Chair

This condo lies in the heart of the original Jay Village, offering flexible living space for a larger family or group and the best of Jay's ski-on ski-off locations. With a well stocked kitchen and central great living area as well as 5 bedrooms and a den, everyone can have the space that they need. Private entrance with a mud room and ski locker. Free parking. Access to the Jay Peak Resort facilities, including pool, water park and skating rink are available for a fee to the resort.

4.94 out of 5 average rating, 158 reviews

A cozy living area features a built-in conversation pit surrounding a modern fireplace. Natural light streams in from large windows, illuminating comfortable seating adorned with colorful cushions. Wooden bookshelves filled with books create a warm and inviting backdrop.

Townhouse in Stowe

Ski In Ski Out, Chic, Fun, Cozy, Grt Location!

Ideal location! Ski/bike/hike right from our front door, and also minutes to the best of Stowe restaurants, craft breweries, shopping, trails & swimming holes. We like staying in stylish boutique hotels, so we decorated our country home to feel like one. 3 bedrooms each on own level, two baths, spotless, stylish, foosball, strong Wi-Fi and cozy fireplace conversation pit - so nice for playing boardgames and watching movies. We welcome you to enjoy our home and the magic of Stowe!

4.97 out of 5 average rating, 155 reviews

A modern kitchen is equipped with stainless steel appliances and a spacious island featuring bar seating. Natural light filters through large windows, illuminating the area. A cozy living space is visible in the background, furnished with a sectional sofa and decorative cushions.

Chalet in Orford

Le Style Orford CITQ 296122 expiration 2027-06-30

SUPERBE Chalet/Condo sur 2 étages incluant 2 grandes terrasses couvertes avec BBQ. Nouvellement meublé, construit en 2017 et décoré de style chic-rustique, vous serez à moins de 5km de la station de ski Orford, de 2km du Golf Mont-Orford, et à 6km du Centre-Ville de Magog et ses plages. Randonnées pédestres, pistes cyclables, Parc de la SÉPAC, Orford Musique, saison des couleurs, tout est à votre portée afin de pratiquer vos activités favorites -membre CITQ 296122

5.0 out of 5 average rating, 179 reviews

A rustic cabin with a wooden exterior is surrounded by lush greenery. The inviting porch features several rocking chairs and is accessed by steps from a grassy area, while a gravel driveway leads to the entrance, enhancing the private setting.

Cabin in Wolcott

Meadow Woods Cabin, private, cozy and unconnected

Enjoy beautiful sunsets from your rocking chair on the cabin's wonderful porch. There is a large, well equipped kitchen, open space floor plan, new shower unit and plenty of closet space in the bedroom. Easy access to VAST snowmobile trails, within an hour's drive to 3 ski areas (Stowe, Smuggler's Notch and Jay Peak), X-Country skiing right outside the door or in Craftsbury or Stowe. Elmore State Park is 3 miles away. Hiking trails and kayaking abound!

4.97 out of 5 average rating, 177 reviews

An open-concept living area is presented with a mix of comfortable seating, a wooden dining table, and a well-equipped kitchen. Large windows allow natural light to fill the space, and wooden beams create a warm ambiance, while stone accents add texture.

Home in Elmore

The Maple Lodge at Lake Elmore

The Maple Lodge at Lake Elmore is a two bedroom handcrafted home located between Montpelier and Stowe Vermont. Nearby skiing, hiking and seasonal recreation opportunities await your visit. The Elmore State Park provides a wonderful beach and watercraft rental & hiking trails for Mount Elmore. Close to the Lamoille Valley Rail Trail-a 90 mile walking/biking/snowmobile trail. There is a 24 hour supermarket, restaurants, shopping, & hospital.

4.98 out of 5 average rating, 204 reviews

The house is set against a backdrop of vibrant fall foliage, with a blend of yellow and red leaves surrounding it. Large windows reflect the colors of the trees, while the modern architecture adds to its charm. The scene conveys a harmonious connection with nature.

Home in Stowe

Spacious Eco-Friendly Stowe Home for Family Fun

Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

Popular amenities for Jay ski-in/ski-out rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

4.86 out of 5 average rating, 130 reviews

Home in Glover

Family Retreat | 50 Private Acres | Mountain Views

4.86 out of 5 average rating, 415 reviews

A rustic barn stands beneath a star-filled sky, with the Milky Way clearly visible. The structure, weathered and wooden, is illuminated gently by the surrounding landscape, providing a stark yet captivating contrast to the deep blues and purples of the night sky.

Home in Westford

1797 Vt Farm House See the Stars!

4.95 out of 5 average rating, 40 reviews

Home in Jay

The Grammy Jay Chalet: 4BR/4BA Ski In/Out Condo

5.0 out of 5 average rating, 18 reviews

Home in Jay

Ski In/Out - Trailside Condo - 2 Bedroom

4.97 out of 5 average rating, 71 reviews

The exterior of a charming two-story house is surrounded by lush greenery and colorful shrubs. A well-maintained lawn leads up to the house, which features classic windows and rooflines. A few trees provide shade, enhancing the tranquil setting.

Home in Craftsbury

Chandler House: Picture Perfect

5.0 out of 5 average rating, 57 reviews

A charming wooden cabin is set against a backdrop of lush greenery, positioned on a slight elevation by the lake. A spacious deck is visible, equipped with seating, inviting relaxation while enjoying the natural surroundings. The bright blue sky complements the vibrant landscape.

Home in Craftsbury

The Glass House

4.97 out of 5 average rating, 91 reviews

A spacious cottage is surrounded by trees, showcasing a lush green lawn. Red and white Adirondack chairs are arranged around a stone fire pit in the foreground. The cottage's two-story structure, accented by large windows and a deck, is visible under a bright blue sky with scattered clouds.

Home in Mansonville

Le chalet Vale Perkins

4.94 out of 5 average rating, 16 reviews

Home in Stanstead

Le Love!

Family-friendly, ski-in/ski-out home rentals

4.94 out of 5 average rating, 267 reviews

A spacious dining area features a large wooden table surrounded by four light-toned chairs. Natural light floods in through two large windows, with soft drapes framing the view. A contemporary light fixture hangs above the table, while a fireplace is positioned nearby for added warmth.

Condo in Bromont

Lumineux condo ski in/out au pied de la montagne!

4.93 out of 5 average rating, 55 reviews

"The Jay Chalet" *cozy* ski in/out condo at Jay

5.0 out of 5 average rating, 67 reviews

Best Location New Ski-In/Out A/C Dogs by Waterpark

A cozy living area features a comfortable brown sofa and two gray chairs, arranged around a light wood coffee table. A stone fireplace is situated against a wall, with a television mounted above it. Soft lighting enhances the inviting ambiance.

4.99 out of 5 average rating, 90 reviews

2 BR.SLOPESIDE CONDO WALK 2 WATERPARK/RINK/ TRAILS

5.0 out of 5 average rating, 17 reviews

Townhouse in Jay

Jay Peak 2BR/2BA Ski-in/Ski Out V341

5.0 out of 5 average rating, 33 reviews

Apartment in Jay

Absolute best ski on/off at Jay.

5.0 out of 5 average rating, 9 reviews

Jay Peak Ski in Ski out Trailside condo

4.86 out of 5 average rating, 22 reviews

The living room features a cozy gas fireplace framed by light-colored wood. Large windows allow natural light to fill the space, highlighting a green sofa set and a rustic rocking chair. A wooden coffee table and two log-style stools complete the inviting atmosphere.

Apartment in Jay

Ski in/ski out Jay Peak condo with view of slopes

Ski-in/ski-out cabin rentals

An A-frame cabin is nestled among trees, showcasing a snow-covered roof and large windows. A wooden deck features a stacked firewood pile, and a decorative wreath adorns the entrance. Soft sunlight filters through the surrounding greenery, creating a serene winter scene.

Cabin in Jay

The Bear's Den at Jay

4.68 out of 5 average rating, 271 reviews

The cabin exterior is characterized by rustic wooden siding and a sloped metal roof. Large windows allow natural light into the interior. A spacious front porch provides access to the surrounding greenery. Trees create a natural backdrop, enhancing the secluded atmosphere.

Cabin in Victory

Northeast Kingdom Cabin @Victory Hill Trailside

5.0 out of 5 average rating, 3 reviews

4.92 out of 5 average rating, 84 reviews

A wooden cabin stands amidst a snowy landscape, featuring a small pond partially frozen in the foreground. The surrounding trees display a dusting of snow, creating a serene winter atmosphere. Bright blue skies complement the tranquil scene.

Cabin in Montpelier

Custom Cabin, Stowe/Montpelier (Family Bunk Room)