Family-Friendly rentals near Okemo Mountain Resort

4.98 out of 5 average rating, 129 reviews

An open-concept kitchen and living area are highlighted by high ceilings and large windows, allowing natural light to fill the space. A central island with a dark countertop complements the cabinetry, while a cozy seating area is visible through expansive glass doors opening to the outdoors.

Home in Windsor

Stylish Vermont Cabin | Views · Trails · Luxe

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

4.88 out of 5 average rating, 160 reviews

The charming treehouse is perched on stilts among lush greenery, with warm lights outlining the spacious deck. Large windows provide a view of the surrounding landscape, and a welcoming entrance is visible. The natural setting enhances the cabin's rustic appeal.

Treehouse in Londonderry

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.

4.99 out of 5 average rating, 135 reviews

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

4.97 out of 5 average rating, 176 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Newly renovated in fall 2023, this 3-level, 1700+ sq. ft. ski chalet is just a 4 min drive to Okemo Mountain Resort and town, with Jackson Gore only 6 min away. Floor-to-ceiling windows showcase stunning 180-degree views of the wooded backyard, creating a peaceful mountain retreat. Cozy up by the fireplace or soak in the Jacuzzi hot tub for ultimate relaxation. Whether you're here for skiing, hiking, or a quiet escape, this private oasis offers the perfect blend of comfort and convenience.

4.96 out of 5 average rating, 125 reviews

A stone patio is illuminated by string lights, featuring a fire pit surrounded by three adirondack chairs in red, blue, and white. Lush greenery is visible in the background, creating a serene outdoor gathering space.

Apartment in Ludlow

Peaceful Ludlow base for exploring Okemo valley

Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

A modern fire pit is illuminated in the evening, surrounded by a wooden enclosure. The design features an open, triangular mesh body that reveals flickering flames within. Soft light casts a warm glow on nearby seating, providing a cozy atmosphere for gathering.

4.97 out of 5 average rating, 105 reviews

Mountain views - hot tub, games, minutes to lakes

Enjoy our 3900 square ft home with 5 bedrooms and 3 full bathrooms, large kitchen and dual dining areas. Enjoy the Buck Hunter arcade game, a 75-inch TV, a stocked library and shuffleboard table. Relax in the backyard with a fire or a dip in the Jacuzzi hot tub. Sleeps 12. Explore nearby Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby.

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

This is a brand new modern timber frame smart cabin in Ludlow (~5 min from Okemo). The house was recently featured on DIY / Discovery’s acclaimed TV show, Building Off The Grid. Warm up after a day of skiing or riding with heated floors and a walk-in shower. Charge up your electric vehicle in the private garage. Directly access the VAST snowmobile trail from the backyard or sit back on the porch and soak up the views. Message host about renting for next winter season!

4.87 out of 5 average rating, 165 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.

4.95 out of 5 average rating, 894 reviews

The spacious living area features warm wood paneling and a polished floor. A dining area with a wooden table is elevated, while a cozy seating arrangement with colorful cushions is nestled on the ground. Soft lighting from overhead fixtures creates a welcoming ambiance.

Loft in Ludlow

Spacious Renovated Barn Apt on 100 acres!

Our unique hideaway is only two miles from many restaurants and cute shops in Ludlow, and we are 1 mile from the gorgeous Buttermilk Falls and Jackson Gore at Okemo Mountain Resort where you can enjoy mountain biking, a ropes course or skiing and riding! Enjoy 100 acres of hiking or snowshoeing right outside your door. There is nice fire fire pit, hot tub and outdoor seating. Perfect location for the outdoor enthusiast or a relaxing weekend in cool VT air!

A cozy living room features warm wooden paneling and a plush sofa facing a mounted flat-screen television. A circular coffee table sits in the center, complemented by a floor lamp and a side chair. A fireplace adds a comforting touch, creating a welcoming space.

4.95 out of 5 average rating, 190 reviews

Lovely 1-Bedroom condo with indoor fireplace!

This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.

4.93 out of 5 average rating, 175 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Please note there is no AC at this condo complex summer time

4.86 out of 5 average rating, 335 reviews

Yurt in Mount Holly

Love Shack Yurt on Star Lake (100% off grid)

Glamping at its finest. Bring everything but the bed. Enjoy sunsets and star gazing lakeside. No running water or electricity. Clean & custom built outhouse for a toilet. You will need to bring bedding, size king. Please note: self cleaning policy. Leave it in great condition for your fellow travelers. Woodstove for heat, provide your own wood. One King Bed with mattresses and top sheet ONLY. IG@YURTlilyPAD

Popular amenities for family-friendly rentals near Okemo Mountain Resort

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 122 reviews

The log cabin is viewed from the front, showcasing a welcoming porch with several chairs and warm light emanating from windows. The architectural details reflect a traditional style, surrounded by lush greenery, creating a serene evening ambiance.

Cabin in Ludlow

Cozy Log Cabin with Hot Tub | 1/2 mile to Okemo

4.99 out of 5 average rating, 383 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

4.98 out of 5 average rating, 769 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

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.

4.96 out of 5 average rating, 116 reviews

Winterplace - Steps away from Slopes

4.98 out of 5 average rating, 262 reviews

A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.

Treehouse in Brookline

Glamping Cabin with Hot Tub on Flower Farm

4.91 out of 5 average rating, 269 reviews

A wooden deck is featured in the foreground, leading to a small sitting area with a patterned chair beside a black side table. Lush greenery surrounds the space, providing a natural setting, while a gravel path and stacked firewood are visible in the background.

Tiny home in Clarendon

Secluded tiny house resort - DOG FRIENDLY

4.91 out of 5 average rating, 116 reviews

Yurt in Dover

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

4.95 out of 5 average rating, 198 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

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 120 reviews

The exterior of an 1840s stone house is displayed, featuring a warm red door and large windows under a sloping roof. A well-maintained garden surrounds the entrance, and a tall tree provides shade. A gravel path leads to the house, with a visible stone wall along the yard.

Cottage in Chester

Quaint stone house!

4.94 out of 5 average rating, 129 reviews

A modern cabin is set amidst lush greenery, elevated on stilts for an unobstructed view. The exterior features a mix of wood and dark finishes, with large windows allowing natural light to fill the interior. A gravel path leads to the entrance.

Home in Jamaica

The Post Haus: one-of-a-kind modern VT experience

4.97 out of 5 average rating, 267 reviews

Cabin in Mount Holly

Private Cabin/PetsOK/AC/Minutes to Okemo/Fast Wifi

4.95 out of 5 average rating, 1,057 reviews

Guesthouse in Hartland

Yurt In The Woods - Come to the Yurt.

4.98 out of 5 average rating, 231 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!

The exterior of a cozy house is presented, featuring a sloped metal roof and green siding. Large windows with white trim provide natural light. Lush greenery and trees surround the property, creating a serene atmosphere, while a pathway leads toward the entrance.

4.96 out of 5 average rating, 111 reviews

Ludlow Village/Okemo Shuttle - Oma K's Kottage

4.78 out of 5 average rating, 110 reviews

Cabin in Mount Holly

Ladybug Cottage - near Okemo

4.95 out of 5 average rating, 103 reviews

A inviting corner of the cabin showcases a light-colored armchair beside a wooden cabinet. Soft natural light filters through two windows adorned with simple treatments, illuminating the warm wooden walls. A wood-burning stove stands nearby, enhancing the rustic charm of the space.

Cabin in Cavendish

Copper Hill House - VT getaway near Ludlow & Okemo

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 316 reviews

Townhouse in Killington

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

4.91 out of 5 average rating, 999 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

5 out of 5 average rating, 103 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

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

4.92 out of 5 average rating, 114 reviews

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

4.97 out of 5 average rating, 144 reviews

A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.

Townhouse in Killington

Beautiful Spacious Condo at Killington Resort

4.99 out of 5 average rating, 287 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

4.97 out of 5 average rating, 106 reviews

A spacious family room features a vaulted ceiling with wooden beams. Seating includes a sectional sofa and two lounge chairs. A large smart TV is mounted above a minimalist fireplace. Natural light floods in from the expansive glass doors leading to a balcony.

Cottage in Wardsboro

Modern Cottage between Stratton and Mount Snow VT

5 out of 5 average rating, 126 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Family-friendly home rentals with Wifi

4.99 out of 5 average rating, 107 reviews

The living area features a spacious sofa and armchair, framed by large windows that provide ample natural light. Exposed wooden beams run along the ceiling. A decorative rug adds color to the hardwood floor, and a mantelpiece serves as a focal point in the room.

Home in Tinmouth

Charming Vermont Schoolhouse

A cozy living area features a stone fireplace with a warm fire, surrounded by a modern sofa. Above the fireplace, a wall-mounted television is visible. A rustic chandelier with multiple bulbs hangs over a dining table, while decorative items are placed on a nearby side table.

4.95 out of 5 average rating, 37 reviews

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

5 out of 5 average rating, 41 reviews

An open living space features warm wooden flooring and a staircase leading to sleeping areas. A dining table with wooden chairs sits beside a modern kitchen, characterized by stainless steel appliances. A cozy couch is positioned next to a textured throw, inviting relaxation.

Cabin in Weathersfield

Cozy a-frame w loft, new kitchen + mins to hiking

5 out of 5 average rating, 12 reviews

Apartment in Ludlow

Cozy Mountain-style Condo by Okemo with a View!

4.98 out of 5 average rating, 181 reviews

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

Home in West Windsor

Birdie's Nest Guesthouse

4.98 out of 5 average rating, 293 reviews

An organically shaped mini-house is surrounded by lush greenery, with a stone pathway leading to a softly lit entrance. The structure features unique, curvaceous walls and several windows, harmoniously blending with the natural landscape of trees and foliage.

Home in Pownal

Cozy Vermont mini-house

Superhost

The timber frame house is surrounded by dense trees, showcasing a natural setting. Large windows illuminate the exterior, providing glimpses of the interior. Sturdy wooden steps lead to the door, enhancing accessibility amid the forest environment.

Tiny home in Athens

4.91 out of 5 average rating, 244 reviews

Luxury “Tiny” House With Sauna (Timbery)

A cozy living area features a comfortable sofa and armchair facing a modern electric fireplace. Natural light floods in from large windows, with a dining table nearby. Textured wall details and neutral tones create a warm ambiance throughout the space.