Family-friendly holiday rentals in Cavendish

4.97 out of 5 average rating, 109 reviews

A log cabin is set amidst a snowy landscape, featuring a large wrap-around deck that offers outdoor seating. Snow blankets the ground and the roof, while evergreen trees frame the property, enhancing the secluded ambiance. The stone chimney rises from the cabin, suggesting warmth inside.

Cabin in Cavendish

Cozy VT Log Cabin Minutes to Okemo & Killington

Get away to Pine Ridge Cabin! A secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your morning coffee on the large wrap around deck overlooking Elm Brook before your day hiking, brewery hopping, or hitting the slopes! The cabin provides open floor plans centered around the large stone face fireplace, the perfect space for gatherings of family, friends, or a couples retreat! Pine Ridge Cabin is only a few minutes to town, shopping, restaurants, bars, and spa!

KitchenIndoor spacesLaundry

4.98 out of 5 average rating, 177 reviews

A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.

Treehouse in Hancock

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

KitchenFamilyCleanliness

A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.

5.0 out of 5 average rating, 132 reviews

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

Indoor spacesKitchenLaundry

4.97 out of 5 average rating, 462 reviews

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Indoor spacesKitchenWi-Fi

4.96 out of 5 average rating, 108 reviews

Tiny home in Ludlow

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Indoor spacesKitchenDecor

4.97 out of 5 average rating, 145 reviews

A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.

Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

FamilyIndoor spacesOutdoor spaces

4.88 out of 5 average rating, 169 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

KitchenFamilyDecor

4.96 out of 5 average rating, 112 reviews

A modern two-story cabin, featuring a rich red exterior, is nestled among autumn trees. Large windows allow natural light to fill the interior. A seating area with dark chairs is positioned around a fire pit, accentuating the outdoor space surrounded by colorful fall foliage.

Cabin in Cavendish

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

FamilyIndoor spacesLaundry

Superhost

A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.

Tiny home in Athens

4.86 out of 5 average rating, 185 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

FamilyKitchenGetting around

4.96 out of 5 average rating, 202 reviews

The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.

Cabin in Townshend

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

FamilyIndoor spacesWi-Fi

4.95 out of 5 average rating, 128 reviews

VT Retreat: Hot tub | pool table | 70” TV | bbq

Come and stay in this extraordinary Cavendish home filled with historical charm yet fully updated with all the modern amenities you have come to expect. Our home has everything you need for your getaway. Gourmet kitchen, BBQ, Hot Tub, 2 master suites, games room, pool table, 70" TV, and window A/C's in all the bedrooms. Located just a short drive to many of Vermont's summer and winter attractions.

FamilyIndoor spacesHiking

The exterior of the renovated schoolhouse is illuminated at dusk, showcasing large windows that reflect a warm glow from within. The distinctive architectural features are highlighted against a twilight sky, with trees positioned in the background.

4.94 out of 5 average rating, 111 reviews

Renovated Vermont Schoolhouse – Close to Okemo

Time for recess! Our totally renovated and expanded schoolhouse is a perfect retreat with all the comforts of home. It has high ceilings, lots of natural light, and plenty of spaces to gather or have some quiet time. Fully stocked kitchen w/DW. 3 bdrms (3 beds, 2 queen/1 full), 2.5 baths. W/D. Close to Ludlow, Okemo/Jackson Gore, Stratton, Killington, Castle Hill Spa and plenty of lakes and ponds.

KitchenFamilyLong stay

Popular amenities for Cavendish family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 130 reviews

The cabin entrance is framed by freshly fallen snow, with wooden siding that blends into the winter landscape. A lantern on the left provides a soft glow, illuminating the path. Tranquil trees surround the area, enhancing the serene atmosphere.

Cabin in Plymouth

~The ClubHaus~

KitchenIndoor spacesValue

4.95 out of 5 average rating, 260 reviews

The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.

Cabin in Londonderry

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Indoor spacesKitchenCheckout

4.96 out of 5 average rating, 181 reviews

The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.

Tiny home in Chester

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

FamilyIndoor spacesHospitality

Guest suite in Brownsville/West Windsor

The exterior of a charming farmhouse features a green metal roof and white siding, surrounded by lush greenery. Flowering shrubs in the foreground add a touch of natural beauty, complementing the tranquil rural setting. Blue skies and scattered clouds provide a serene backdrop.

5.0 out of 5 average rating, 211 reviews

Cozy Guest Suite in VT Farmhouse

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 395 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

KitchenFamilyNearby

4.93 out of 5 average rating, 300 reviews

A rustic cabin is nestled among the trees, showcasing its wooden exterior and a metal roof. Tall windows allow natural light to fill the space. Surrounding greenery, including ferns and bushes, adds to the secluded atmosphere. A stone wall and picnic table can be seen in front.

Cabin in Sharon

forest retreat; off-grid writers cabin

KitchenFamilyCondition

4.98 out of 5 average rating, 777 reviews

An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.

Cottage in Shaftsbury

Schoolhouse Spa Retreat on a Vermont Farm

Indoor spacesKitchenLayout

A serene winter scene captures a two-story house blanketed in fresh snow. Flakes gently fall, creating a soft ambiance. The front yard features a large evergreen tree, while the warm glow of an interior light is visible through a window, hinting at a cozy atmosphere inside.

4.84 out of 5 average rating, 158 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 14

FamilyIndoor spacesParking

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 102 reviews

Home in Reading

Private, Large 4BR home | Pet friendly | 10 Acres

FamilyIndoor spacesView

4.99 out of 5 average rating, 152 reviews

A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Indoor spacesKitchenSleep quality

4.87 out of 5 average rating, 104 reviews

Home in Chester

Charming Chester Farmhouse Near VT Slopes

Indoor spacesKitchenCleanliness

4.98 out of 5 average rating, 235 reviews

A rustic cabin is nestled among vibrant wildflowers and lush greenery. A variety of flowers, including purple and yellow blooms, frame the scene, leading the eye towards the charming structure with a classic metal roof and wooden accents.

Home in West Windsor

Meadow View. 35 acres outside your door!

Indoor spacesKitchenQuiet

4.95 out of 5 average rating, 109 reviews

The modern timber frame cabin features a covered porch with wooden beams, providing a welcoming entry. Large windows offer views of the surrounding forest, while a landscaped path leads to the entrance, framed by lush greenery and natural stone steps.

Cabin in Ludlow

Modern Okemo Smart Cabin - As Seen On DIY Channel

FamilyIndoor spacesView

4.97 out of 5 average rating, 134 reviews

A charming red exterior defines the recently built house, surrounded by lush greenery and a clear sky. The spacious porch features rustic columns, while comfortable seating invites relaxation. Large windows ensure natural light fills the interior, offering a connection to the serene outdoor environment.

Home in Windsor

Custom cabin on Mt Ascutney, with faraway views

KitchenIndoor spacesDecor

4.97 out of 5 average rating, 237 reviews

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

Cabin on the Hill

Indoor spacesFamilyBiking

4.9 out of 5 average rating, 207 reviews

A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.

Bus in Granville

Serene Bus Getaway Among Rolling Farm Land

Indoor spacesKitchenPets

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 108 reviews

A gravel road leads through open fields bordered by manicured greenery. In the distance, rustic buildings and trees with autumn foliage are visible against a clear blue sky, creating a serene rural landscape.

Farm stay in Clarendon

Dream Catcher Farm

FamilyIndoor spacesComfort

4.96 out of 5 average rating, 138 reviews

Home in Springfield

Ski Mountain View Estate

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 175 reviews

A red wooden cabin nestled among trees, showcasing a welcoming front porch. Air conditioning units are situated to the side. Natural light filters through the foliage, creating a serene and shaded outdoor atmosphere.

Barn in Newfane

Beautiful rustic woods and fields retreat.

KitchenIndoor spacesShared spaces

5.0 out of 5 average rating, 131 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Indoor spacesKitchenLocation

4.99 out of 5 average rating, 293 reviews

Exposed wooden beams frame the room, complemented by warm brick walls. A cozy fireplace sits centered against the wall, with decorative art above it. A comfortable chair and lamp are positioned nearby, while a television and small dresser provide functional elements in the living space.

Cottage in Newfane

Cozy Vermont Antique Sugar House with Fireplace

FamilyKitchenAmenities

4.96 out of 5 average rating, 116 reviews

The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.

Condo in Ludlow

Winterplace - Steps away from Slopes

KitchenFamilyHot tub

4.91 out of 5 average rating, 1012 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

FamilyKitchenBathroom