Family-friendly holiday rentals in Jay

4.87 out of 5 average rating, 366 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

Indoor spacesFamilyBathroom

4.95 out of 5 average rating, 260 reviews

The wooden cabin, characterized by a pitched roof and large front deck, is nestled in a grassy area surrounded by trees. A stack of firewood is neatly arranged beneath the deck, while a dog is seen exploring the green lawn.

Home in Westfield

Jay Peak 3 miles - secluded with spectacular view!

Mountains, streams & seclusion! • Hike the Long Trail • Road, gravel & mountain biking • Jay Peak Resort is three miles away! • Waterpark • Golf • Backcountry guiding - hiking, kayaking, gravel & mountain biking (15% discount) • Photography and videography (15% discount) This is the mountain getaway you dream about! Our only neighbors are animals in the surrounding mountains & forests. Note: There is also an apt in the main house that sleeps 8. Welcome to Vermont Mountain Experience!

KitchenFamilyWi-Fi

4.97 out of 5 average rating, 329 reviews

A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.

Treehouse in Newport

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

FamilyKitchenComfort

A cozy bedroom is presented with a spacious bed dressed in crisp white linens. Two decorative yellow pillows sit against the headboard, while a basket of sunflowers is positioned on the windowsill. Snow is visible outside the two windows, providing a bright winter view.

4.81 out of 5 average rating, 165 reviews

Fabulous Jay Peak ski-in/ski out condo!

Your family will be close to everything when you stay at this centrally-located condo. You are steps to the pool and water park (water park tickets sold separately). Plenty of dining options, hiking and golf are within walking distance. In the winter, enjoy the ski-in and ski-out location. This condo has a fully stocked kitchen, a dining area and a living room with a smart tv and cable. The master bedroom has a queen-sized bed with a smart tv. The second bedroom has a full and two twins.

FamilyKitchenValue

4.97 out of 5 average rating, 194 reviews

A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.

Treehouse in Moretown

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley! No pets or animals please.

Indoor spacesKitchenWalkability

4.94 out of 5 average rating, 183 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 stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, fire pit, and plush outdoor chairs. 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!! Long Trail hiking entrance close to the cabin.

FamilyIndoor spacesLaundry

4.99 out of 5 average rating, 162 reviews

Home in Richford

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Our guest farmhouse, located 1 mile from the Canadian border, is close to Jay Peak Ski Resort and Mount Sutton. Mountain and meadow views are spectacular from every window! Here, you are perfectly poised to explore both the quaint, foodie-focused, French-Canadian, Eastern Townships, just across the border in Quebec AND the scenic back-roads, abundant lakes, family farms, mountain trails, local pubs, and old general stores of Northern Vermont. Or just enjoy the porch & peaceful atmosphere!

Indoor spacesFamilyTV

Superhost

The front exterior of a historical cottage is framed by lush green trees and blooming lilac bushes, providing a vibrant contrast against the structure. A small porch is visible, offering a view of the surrounding nature.

Cottage in Westfield

4.89 out of 5 average rating, 194 reviews

Historic Schoolhouse Minutes From Jay Peak

After a long day of hiking, biking, or skiing, come take a swing at our charming historical cottage. Dating back to the mid 1800s it was one of the first schoolhouses in the area, today it is filled with all the modern luxuries one would need. Our quaint porch is perfect for bird watching or leaf peeping. The inside includes high ceilings, a bedroom and a cozy loft- both with queen beds. French culture is only a 10 min drive away; Vermont culture is abound with maple syrup and warm locals.

FamilyIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 112 reviews

The exterior of a three-story condo is presented, featuring a modern design in muted grey tones. Snow blankets the ground, and nearby trees stand tall against a backdrop of mountains. The building’s entrance is accessible, with a sign labeled 'Mountainside' visible.

Apartment in Jay

Condo with all amenities M105

Mountainside 105 Located right next to the Ice Haus skating arena, this condo is the perfect home away from home for families traveling with kids! When you book this condo, you and your guests will be a short walking distance to Jay Peak Resort amenities, including indoor and outdoor pools, the incredible, year-round Pump House indoor waterpark and arcade. JAY PEAK RESORT AMENITIES - Indoor and outdoor pools - Sauna - Lazy river - Indoor waterpark - Climbing center - Restaurant

KitchenIndoor spacesAir conditioning

4.93 out of 5 average rating, 132 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!

FamilyKitchenOutdoor spaces

Superhost

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.

4.82 out of 5 average rating, 293 reviews

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!

FamilyKitchenQuiet

4.96 out of 5 average rating, 295 reviews

The living area features high ceilings with exposed beams, allowing natural light to fill the space. A comfortable sofa is paired with accent chairs and a wood coffee table. A gas fireplace adds warmth, while a wall-mounted TV enhances entertainment options.

Chalet in Westfield

Mountain View Chalet near Jay Peak!

Welcome to your mountain getaway! Come unwind at this recently renovated chalet. The main living area and kitchen are perfect for all types of groups; couples, families and adventurers, and your pets! There are 13 acres to play (snowshoe, cross country ski, sledding, hiking or just relaxing) and only 20 minutes to awesome skiing or riding at Jay Peak! The views/sunsets from the property are breathtaking. 3 bedrooms, 2 baths across 2 floors.

KitchenFamilyAmenities

Popular amenities for Jay family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 210 reviews

An outdoor area features a hot tub under a wooden gazebo, surrounded by a stone patio. Relaxation spaces include two wooden chairs and a circular sauna, with a serene forest backdrop providing privacy and tranquility.

Chalet in Mansonville

Scandinavian chalet • Sauna spa • Quiet nature

Indoor spacesFamilyOutdoor spaces

4.99 out of 5 average rating, 197 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

FamilyIndoor spacesWalkability

4.86 out of 5 average rating, 111 reviews

The exterior of a log cabin is displayed, featuring a spacious deck with a hot tub and an inviting green Adirondack chair. Surrounding trees display autumn colors, enhancing the natural setting. The structure showcases multiple angles and windows, emphasizing its unique architecture.

Cabin in Bakersfield

Modern 3-BD Mountain Cabin w/ Hot Tub, Deck, Loft

FamilyIndoor spacesWi-Fi

Superhost

Home in Eden

4.92 out of 5 average rating, 170 reviews

SleepUnderThe Stars-Lakefront|Hot Tub|GameRm|Pets!

FamilyKitchenHeating

4.93 out of 5 average rating, 133 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

Indoor spacesFamilyCheckout

4.97 out of 5 average rating, 116 reviews

Chalet in West Brome

The Old School | Spa | Natural Park | Countryside

FamilyIndoor spacesAir conditioning

4.96 out of 5 average rating, 207 reviews

A dining area features a round table surrounded by six black chairs, with a view of snow-covered trees visible through large windows. A cozy sitting area is seen to one side, complemented by a fireplace and natural wooden accents in the ceiling and decor.

Tiny home in Mansonville

La Cabine Potton

KitchenFamilyLayout

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.

4.92 out of 5 average rating, 180 reviews

Ski in Ski out - fantastic location on the trail

FamilyKitchenLaundry

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 884 reviews

The treehouse stands tall on wooden supports among a dense forest of tall trees. Its wooden exterior features a spacious deck with railings, while warm light glows from within, casting a welcoming ambiance. The natural surroundings create a serene atmosphere.

Treehouse in Hardwick

Streamside Treehouse in the Woods with Sauna

Indoor spacesFamilyAccuracy

4.96 out of 5 average rating, 142 reviews

Yurt in Newport

Vermont Yurt Farm Stay | Vermont Glamping

Indoor spacesFamilyBreakfast

5 out of 5 average rating, 296 reviews

A modern cabin is nestled among tall trees, elevated on stilts. Large windows offer a glimpse of the interior space, featuring a minimalist design. The surrounding greenery creates a natural setting, while the pathway leading to the cabin is lined with earth tones.

Cabin in Morristown

Cady’s Falls Cabin

KitchenFamilyPets

4.97 out of 5 average rating, 144 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

Indoor spacesKitchenLayout

4.95 out of 5 average rating, 159 reviews

Cabin in Jay

Mountain views of Jay Peak- with 2nd cabin add-on!

KitchenFamilyParks

4.96 out of 5 average rating, 139 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

FamilyIndoor spacesHospitality

4.87 out of 5 average rating, 107 reviews

A charming farmhouse is showcased alongside a separate guest building, surrounded by lush greenery and trees. The white exterior is complemented by red accents at the entryways. The well-maintained lawn provides a welcoming approach, highlighting the peaceful rural setting.

Home in Jay

Entire Rustic Farmhouse minutes from Jay Peak

FamilyIndoor spacesBiking

4.98 out of 5 average rating, 130 reviews

A rustic cabin stands surrounded by autumn foliage, showcasing wooden siding and two front windows. The covered porch features a set of outdoor chairs, inviting guests to sit and enjoy nature. Layers of fallen leaves create a colorful carpet at the cabin's base.

Cabin in Danville

The Cabin

KitchenFamilyNearby

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 188 reviews

The outdoor area features a heated lap pool surrounded by lush greenery and a well-kept lawn. An intimate patio area with lounge chairs and shaded umbrellas is visible, alongside a charming seating arrangement for gatherings. The elegant home serves as a backdrop to this serene setting.

Cottage in Hatley

Hatley House - Pool, Garden, Cycling

FamilyKitchenSleep quality

Guesthouse in Montgomery Center

A guest cabin nestled in the woods is visible, featuring a spacious green yard and a flowing brook nearby. A hammock hangs between trees, while red outdoor chairs are arranged around a stone fire pit. The cabin's elevated deck overlooks the serene landscape.

4.97 out of 5 average rating, 405 reviews

Cabin in the Woods VT - Discount Jay Peak Lift Tix

Indoor spacesFamilyBarbecue

Directional signs are positioned on a pole against a vibrant sunset backdrop. The signs indicate various nearby locations, with a gradient of warm colors filling the sky, creating a serene transition from day to night.

4.99 out of 5 average rating, 156 reviews

Jay Peak Ski in Ski out Condo

KitchenIndoor spacesBathroom

4.86 out of 5 average rating, 107 reviews

A single-story chalet with a wooden exterior is set within a lush green landscape. The entrance features double doors that lead to a well-lit interior. A patio with a red umbrella is visible, along with a winding stone pathway surrounded by various plants and flowers.

Chalet in North Hatley

North Hatley Pavilion Cottage - 2 bedrooms

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 329 reviews

The heated in-ground pool is framed by a spacious patio, showcasing a view of the Richelieu River at sunset. Lush greenery surrounds the area, with a fence enhancing privacy. Comfortable seating arrangements are present near the pool, creating a welcoming outdoor space for relaxation.

Cottage in Noyan

Sunset Cottage on the Richelieu River CITQ#302701

Indoor spacesKitchenBathroom

4.99 out of 5 average rating, 277 reviews

A wooden bench with a decorative wrought iron back is positioned in front of a sign reading 'The House of the Setting Sun.' Lush greenery surrounds the bench, and a small rabbit is situated nearby, creating a peaceful outdoor scene.

Apartment in Newport

The House of the Setting Sun, Private Apartment

Indoor spacesFamilyAir conditioning

4.86 out of 5 average rating, 411 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

KitchenFamilyWalkability