Family-friendly holiday rentals in Jay

4.87 out of 5 average rating, 331 reviews

The exterior of a contemporary timber frame house is shown, featuring a covered porch with seating arrangements. Wood stacked neatly at the base adds to the rustic charm. A sloped roof peaks at the top, and large windows allow natural light to enter.

Apartment in Jay

Jay Apartment

Only 10 minutes to Jay Peak Ski Resort. Secluded in the woods right next to Starr Brook, yet only a 2 min drive to the Jay Village Inn restaurant and bar and the Jay Country Store. Fire pit with cooking grate next to the brook you are welcome to use weather permitting. Great hiking, biking trails, snow showing and Nordic skiing minutes away. Some trails are accessible directly from the property. Very comfy bed, wonderful place to sleep. . Vermont Meals and Rooms Tax ID number is MRT-10126712

4.95 out of 5 average rating, 217 reviews

Home in Westfield

Jay Peak 3 miles - ski home via Big Jay!

Best backcountry skiing in New England - mountain getaway with stunning views! • Jay Peak Resort 3 miles away! • Ski home from Jay Peak via Big Jay! • Backcountry ski 6 mountains from your door! • Tour Long Trail, Catamount Trail, Big Jay & Little Jay from here! • Backcountry guiding available (15% discount for guests!) Note: There is also an apt in the main house that sleeps 8. • Vermont Mountain Experience: guests get a 15% discount for photography, backcountry & resort guiding!

4.94 out of 5 average rating, 231 reviews

The exterior of Alder Brook Cottage is shown, featuring rustic wooden siding and a metal roof. A wooden footbridge leads to the front door, surrounded by trees and patches of snow. Bright windows are visible, enhancing the cabin's inviting appearance.

Tiny home in Hardwick

Alder Brook Cottage: A Tiny House in the Woods

From the moment you cross the cedar footbridge over Alder Brook, you'll know you're somewhere special. Featured in Boston Magazine and CabinPorn, Alder Brook Cottage is an inspired, rustic dream cabin located in the woods of Vermont's Northeast Kingdom. Surrounded by a crystal clear stream and 1400 acres of rugged forest, it is the perfect getaway for glampers looking to experience the tiny house life. Minutes away from Caspian Lake, Hill Farmstead Brewery & Craftsbury Outdoor Center.

4.98 out of 5 average rating, 102 reviews

Cottage in Montgomery

Crofter's Green @ Jay Peak: O'Shea Farmhouse

The O'Shea Farmhouse is one of five micro-cottages at Crofter's Green - our small, thoughtfully-designed lodging property in the heart of Vermont. This cozy woodland retreat is just minutes from Jay Peak Ski Resort and the warm, eclectic town of Montgomery Center. this bright 2-story cottage sits at the forest's edge and offers a peaceful home base for exploring the Northeast Kingdom. It's simple, comfortable, and surrounded by nature. Find us on social media! @croftersgreen

4.81 out of 5 average rating, 116 reviews

A living area features a comfortable blue sofa, a wooden coffee table, and a matching entertainment center with a television. Two dining chairs are positioned around a table, accompanied by a decorative lamp providing soft light. Dark curtains frame a window, while framed artwork adds character to the room.

Apartment in Newport

Mother in Law Guest Suite.

Take it easy at this unique and tranquil getaway. A home away from home. 1 Bedroom (Queen Bed), private Mother in Law Suite, Fully stocked with everything you need. Cute Coffee bar, Wi-Fi/Streaming Services. Direct access to snowmobile/ATV trails. Enjoy the outdoors by a toasty fire pit, beautiful sunsets, direct access to Lake Memphremagog’s far south end, fishing and canoeing. Only a short 3 mile drive to downtown Newport. Only 30 minutes from Jay Peak or Burke Mountain.

4.94 out of 5 average rating, 145 reviews

A modern living area features a comfortable brown sofa beside a wooden coffee table. Exposed wooden beams run across the ceiling, while a staircase leads to an upper level. Natural light fills the space through large windows, creating a warm and inviting environment.

Cabin in Montgomery

Jay Peak Retreat

The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, and 3.5 from Boston.

4.92 out of 5 average rating, 114 reviews

An aerial view showcases the chalet surrounded by lush greenery and a scenic landscape. The expansive wrap-around deck is visible, complete with outdoor seating and a fire pit. The property offers a gravel driveway and a separate storage shed, enhancing the overall outdoor space.

Chalet in Jay

Journeys End Chalet - Minutes to Jay Peak!

** BEAUTIFUL MOUNTAIN VIEWS** Welcome to the Journeys End Chalet! We are located just a quick 10 minute ride from the base of Jay Peak Resort, home to some of the best skiing and riding in the Northeast. The chalet is set on a beautiful and private 11 acres just a stones throw from the Canadian border. We love all dogs and your well behaved furry friends are welcome in our home. We are located directly on the VAST trail system so bring your snowmobile and enjoy!

4.82 out of 5 average rating, 254 reviews

The spacious living area features hardwood flooring, a large coffee table placed on a patterned rug, and a gas-burning fireplace. Windows adorned with light curtains allow natural light to fill the room. A dining table with four chairs is visible, enhancing the shared living space.

Condo in Jay

Cozy Jay Condo

Welcome to our Mountainside Jay condo! This cozy 525 sq foot studio has a queen murphy bed, a queen sofa bed & a gas burning fireplace. Located directly across the street from the golf course/nordic center, next to the Ice Haus & the Water Park. Walk to the tram in the morning. Great destination for a small family, couples getaway or just a place to rest your head after a long day skiing/boarding. Newly renovated bathroom. Sweet and simple. Pets welcome!

4.92 out of 5 average rating, 509 reviews

An aerial view captures the tiny house nestled within lush greenery, surrounded by a gently winding river. Canoes and kayaks are visible near a private access point, while a serene landscape of trees and water reflects the tranquility of the setting.

Tiny home in Mansonville

Charming Tiny House by the water

Discover our charming Tiny House, ideal for a cozy stay by the river. Enjoy trails on the site and private access to the water. This project, lovingly designed, reflects our happiness to have a safe haven to recharge and practice outdoor activities. We want to share this experience with those looking for a sweet moment of wellness in the countryside. Treat yourself to a moment of serenity, alone or in love, in our little cocoon.

4.92 out of 5 average rating, 180 reviews

The bedroom features a King-sized bed dressed in vibrant blue and yellow bedding. Framed art pieces adorn the walls, complemented by a mirror above a wooden dresser. Soft lighting is provided by a modern table lamp, creating a cozy atmosphere.

Apartment in Montgomery

Dog Friendly Apartment near Jay Peak

Enjoy the beauty of Montgomery, Vermont while staying in a very spacious 1-bedroom apartment that is attached to an 1880s farmhouse with a large backyard, garden and and orchard. The apartment is a 15-20 minute drive to Jay Peak Resort and a 3 minute drive to a grocery store and restaurants. It is walking distance from the Hutchins covered bridge and there is private access to the river. Excellent walking for your dog(s)!

4.97 out of 5 average rating, 183 reviews

An expansive green lawn rolls gently down to a serene pond, reflecting the surrounding landscape. Vibrant autumn foliage lines the horizon, transitioning from green to warm tones. The distant mountain range is partially obscured by soft clouds, adding depth to the scenic view.

Apartment in Troy

Jay Peak Getaway

Clean and cozy apartment with private entrance and parking space. Located minutes from Jay peak ski lifts, local biking & hiking, Newport shopping and Canada. Located on a 10 acre parcel with spectacular views of Jay Peak mountain range. Outdoor enthusiasts will love the many activities available in Winter or Summer. Easily accessible off route 100 on a paved road. Owners are on site and available if needed.

4.88 out of 5 average rating, 257 reviews

The cabin's exterior features a log construction with green window shutters. A wooden porch with railings provides access to the entrance, which is highlighted by a sign reading 'Owls Head.' Snow covers the ground, and a clear blue sky is visible overhead.

Cabin in Lowell

Owls Head

Beautifully kept quaint cabin in the fields overlooking the wonders of Jay Peak. Studio style cabin with queen size bed, additional loft area with a full size mattress topper, bathroom with shower, sink and toilet, kitchenette. There is a porch attached to Owls Head where you can take in the beautiful views of sunrise and sunset while being nestled in the valley below Jay Peak.

Popular amenities for Jay family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5 out of 5 average rating, 157 reviews

A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.

Cottage in Fletcher

Metcalf Pond Camp Convenient to Smugglers Notch

4.92 out of 5 average rating, 119 reviews

A welcoming sign for Trillium Woods is positioned in a vibrant green landscape, with a view of a mountain in the background. Trees surround the area, and a small American flag is planted by the sign, enhancing the natural setting.

Townhouse in Jay

Townhouse at Jay with Sauna + Jacuzzi

4.98 out of 5 average rating, 170 reviews

An aerial view captures a charming barn-style home surrounded by lush greenery, with expansive views of a serene lake in the background. The property features meticulously maintained lawns and a landscape rich in trees, set against a backdrop of rolling hills and distant mountains.

Barn in Hinesburg

Cozy Cabin -Top of Hill with Views

Guest suite in New North End

An outdoor courtyard features a salt-water hot tub and natural wooden seating. Lush greenery envelops the space, creating an intimate feel. A rustic barrel-shaped structure adds a unique element to the design. The ground is covered in smooth gravel, enhancing the serene atmosphere.

4.98 out of 5 average rating, 237 reviews

Sauna, Cold Plunge, Hot Tub, Paddle Boards, Bikes

4.99 out of 5 average rating, 198 reviews

Two unique chalet structures, designed with a modern aesthetic, are situated on a sloped landscape. The buildings feature angular shapes and large glass windows, which reflect the surrounding forest, inviting nature indoors. The ground is covered with natural foliage and rocks.

Chalet in West Bolton

The Binocular: Peaceful Architect Cottage

5 out of 5 average rating, 126 reviews

A cozy living area features a light-colored sofa adorned with decorative pillows, complemented by a leather armchair. A well-equipped kitchen area showcases green cabinetry, a black refrigerator, and various appliances on the countertop, illuminated by wall-mounted lights. The space maintains a warm atmosphere with wooden accents.

Guest suite in Jericho

Guest Suite w/hot tub & fireplace

4.99 out of 5 average rating, 160 reviews

A red-painted two-story house is framed by lush green grass and colorful flower beds. A welcoming porch features two white chairs and wooden barrels. A friendly dog is seated at the entrance, adding a homely touch to the exterior.

Place to stay in Johnson

Château Chavís

4.92 out of 5 average rating, 129 reviews

Tiny home in Cambridge

Fox Den Tiny House w/hot tub 1min to Smuggs

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 494 reviews

The rustic chalet is framed by lush greenery, featuring a classic white exterior with a metal roof. A warm light glows from the window, hinting at a cozy interior. Surrounding foliage adds to the tranquil atmosphere, enhancing the natural setting.

Chalet in Fulford

Typical small old school from 1860

4.98 out of 5 average rating, 852 reviews

Treehouse in Hardwick

Cozy Treehouse with Sauna in the Woods with Stream

4.97 out of 5 average rating, 195 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.

4.99 out of 5 average rating, 380 reviews

The exterior of a cozy loft is framed by trees, featuring a wooden deck adorned with string lights that provide a gentle glow. The entrance is highlighted by large glass doors, leading into the inviting interior space.

Guesthouse in Hinesburg

Hydrangea House on the Hill

4.96 out of 5 average rating, 136 reviews

A blue house with a pitched roof is set against a clear blue sky. Lush green grass surrounds the property, and trees provide a natural border. A person is seen walking across the spacious lawn, highlighting the outdoorsy setting.

Home in Montgomery

Hillwest Mountain View

4.99 out of 5 average rating, 154 reviews

A serene winter landscape displays gently rolling snow-covered hills, with distant mountains rising under a clear blue sky. Small structures are scattered across the meadow, surrounded by sparse trees, creating a peaceful and open atmosphere.

Home in Richford

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Apartment in Saint-Étienne-de-Bolton

A serene landscape features a large pond surrounded by lush greenery and trees. The natural setting illustrates the peacefulness of Ch’i Terra, while a spacious stone house is seen in the background, complementing the tranquil environment.

4.95 out of 5 average rating, 221 reviews

CH'I TERRA gîte-ressourcement between lake and river

4.95 out of 5 average rating, 378 reviews

A cozy cabin with wooden siding is surrounded by a blanket of fresh snow. The structure features large windows and a rounded roof, set against a backdrop of tall evergreen trees. Snow covers the ground, creating a serene winter landscape.

Cabin in Hyde Park

Serene Country Cabins 1 In the heart of Vermont

Family-friendly home rentals with a pool

Apartment in La Haute-Yamaska

A well-lit room features a spacious bed adorned with soft pillows. A wooden desk with chairs is positioned against one wall, complemented by framed artwork. Sheer curtains allow natural light to soften the space, while a small plant adds a touch of greenery.

4.8 out of 5 average rating, 111 reviews

Estrie and fullness

4.93 out of 5 average rating, 224 reviews

A spacious outdoor area is visible, featuring a large tree providing shade. A gravel driveway leads to a charming cottage with a glass-covered porch. Nearby, a separate structure is partially visible, and several chairs are arranged for seating, inviting relaxation in the serene surroundings.

Cottage in Dunham

Quiet stay on 76 acres land with pool!

4.86 out of 5 average rating, 126 reviews

A calm bedroom features a spacious bed with neutral-toned pillows arranged neatly. Soft natural light filters through sheer curtains, illuminating the space. A small side table holds a plant and a lamp, while a stylish woven chair offers additional seating.

Condo in Magog

Waterfront condo with indoor and outdoor pool

4.96 out of 5 average rating, 117 reviews

The living room features tall windows that provide ample natural light and overlook the surrounding wooded area. A stone fireplace is flanked by a television and cozy seating options, including a leather sofa and lounge chairs. A patterned rug adds texture to the wooden floor.

Chalet in Westfield

Cozy Chalet at Jay Peak

4.92 out of 5 average rating, 173 reviews

A balcony features two canvas chairs positioned on a wooden deck. A view of vibrant autumn foliage is visible, with trees displaying shades of orange and yellow against a clear blue sky and scattered clouds.

Condo in Jay

Ski in Ski out - fantastic location on the trail

4.87 out of 5 average rating, 391 reviews

A hot tub is situated beneath a covered gazebo, surrounded by natural foliage. A pathway leads through decorative stones to a cedar sauna in the background, while a gentle mist rises from the hot tub, creating a serene atmosphere.

Chalet in Mansonville

Chalet Potton Cottage - spa, sauna & pool

4.74 out of 5 average rating, 200 reviews

A cozy loft space features a spacious bed with plump pillows against a rustic stone fireplace adorned with decorative stockings. A minimalist TV unit displays a festive scene, with soft lighting highlighting a small Christmas tree nearby.

Loft in Orford

Getaway to Orford, 2 minutes to the mountain