Family-friendly rentals near Okemo Mountain Resort

4.95 out of 5 average rating, 311 reviews

The exterior of a two-story contemporary home is depicted, featuring green-framed windows and a pathway lined with gravel. Adjacent grassy areas and trees create a natural setting. A blue flag flutters near the entrance, enhancing the welcoming feel of the property.

Home in Weston

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

A snow-covered exterior of a two-story house is depicted, showcasing a sloped roof and various architectural features such as arched and circular windows. Surrounding trees enhance the serene winter atmosphere, while a driveway leads up to the entrance.

4.94 out of 5 average rating, 157 reviews

OKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!

Please note: NO SATURDAY CHECKOUTS/INS during Winter season which runs November through April - any other day ok the week is OK :) Saturday check-ins during spring/summer OK with prior approval from host. 5 bedrooms, hot tub and outdoor fire pit, fireplace, loft, sleeps 14, 3 full baths, two living rooms, this Okemo Mountain home is the perfect Vermont getaway within walking distance of the slopes. Our home is nestled in the woods and is the perfect spot to relax, have fun, and enjoy life!

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, 130 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, 172 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.

4.98 out of 5 average rating, 127 reviews

Home in Windsor

Stylish Vermont Cabin | Views · Trails · Luxe

There is something about spring and summer at the Red House that makes you stop and gaze. Watch the hills come back to life from the porch, coffee in hand, as green rolls up the valley and wildflowers take over the fields. Hike or bike to a trailhead five minutes from the front door. Gather around the fire pit and wonder how dark and wide the night sky can be. The Red House sits within reach of some of the best restaurants in New England and patiently awaits the discerning traveler.

4.96 out of 5 average rating, 122 reviews

A modern kitchen features sleek white cabinetry and open shelving displaying glassware and kitchen essentials. A wooden dining table with black chairs provides a gathering space. Stainless steel appliances, including an oven and microwave, complement the stylish design, while a fresh plant adds a touch of greenery.

Flat in Ludlow

Peaceful Ludlow Base 5 minutes to Okemo

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!

4.96 out of 5 average rating, 107 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!

Superhost

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

4.87 out of 5 average rating, 160 reviews

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.

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, 189 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.

4.95 out of 5 average rating, 885 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, cute shops, the gorgeous Buttermilk Falls and we are 1 mile from 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 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.

4.92 out of 5 average rating, 173 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. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

4.96 out of 5 average rating, 191 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.

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

4.99 out of 5 average rating, 128 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~

4.95 out of 5 average rating, 103 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

A cozy living area features a spacious, upholstered sofa and an armchair, complemented by a wooden coffee table. A warm fire burns in the brick fireplace, enhancing the inviting ambiance. Colorful artwork is displayed on the walls, and a patterned rug lies beneath the furniture.

4.87 out of 5 average rating, 213 reviews

2 Doors Down - Modern Farmhouse in Downtown Ludlow

4.99 out of 5 average rating, 212 reviews

The rustic cabin sits amidst a lush green landscape, framed by towering trees. The stone chimney adds character, while the two separate structures showcase a combination of wood siding and modern roofing. Clear blue skies create a serene backdrop for the natural beauty.

Cabin in Landgrove

The Owl’s Nest in Landgrove

4.99 out of 5 average rating, 357 reviews

Tiny home in Wilmington

Beautiful Timber Frame Retreat

4.98 out of 5 average rating, 755 reviews

An elevated deck is softly illuminated by hanging lights, featuring a hot tub and a panoramic barrel sauna. Snow covers the ground, and the landscape is filled with distant hills under a twilight sky, creating a serene outdoor retreat.

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, 114 reviews

Winterplace - Steps away from Slopes

4.94 out of 5 average rating, 124 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 121 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

Superhost

The exterior of a red cabin is surrounded by a snowy landscape. Large windows allow natural light to illuminate the front space, while a simple wooden bench rests on the porch. Pine trees are visible in the background, creating a serene atmosphere.

Cabin in Cavendish

4.94 out of 5 average rating, 181 reviews

The Cozy Little Red Cabin

4.92 out of 5 average rating, 118 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, 157 reviews

Cottage in Hartland

5 miles from Woodstock-Dog Friendly w/FIOS

4.94 out of 5 average rating, 1,340 reviews

The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

4.95 out of 5 average rating, 1,040 reviews

Guest house in Hartland

Yurt In The Woods - Come to the Yurt.

4.82 out of 5 average rating, 175 reviews

An old barn features weathered wooden siding and large windows, set against a backdrop of vibrant autumn foliage. A maple tree with bright orange leaves provides a natural canopy, while a carpet of fallen leaves covers the grassy ground, creating a serene outdoor scene.

Barn in Mount Holly

Mapleside Escape: Sugar/Ski house

4.89 out of 5 average rating, 179 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

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 210 reviews

The cabin interior features rustic wooden walls and a cozy propane heater providing warmth. A small seating area is arranged with cushioned stools in front of the heater. A kitchenette is visible in the background, equipped with basic appliances and utensils.

Tiny home in Brattleboro

Mountain View 4x4 Rustic Cabin Retreat w/Fireplace

4.95 out of 5 average rating, 101 reviews

The living room is furnished with a blue sofa and a light armchair, complemented by wooden side tables and lamps. A coffee table is positioned centrally on a carpeted floor. Walls are adorned with wood paneling and artwork, enhancing the space's rustic charm.

Townhouse in Dover

Cozy Bear- 1 mile to Mt Snow Ski Home

4.98 out of 5 average rating, 108 reviews

A cozy living area features exposed beam ceilings and wood floors. Two comfortable sofas face each other, complemented by a coffee table and side tables with lamps. A staircase leads to the upper level, and a small workspace with a chair is visible in the corner.

Cabin in Hartford

Cozy Quechee Cabin near Woodstock and Killington

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

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.

4.93 out of 5 average rating, 123 reviews

One Bedroom Suite Near Okemo

4.94 out of 5 average rating, 231 reviews

A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.

Apartment in Killington

Newly renovated ski retreat at Killington

4.99 out of 5 average rating, 277 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

5 out of 5 average rating, 123 reviews

Chalet in Wilmington

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Family-friendly home rentals with wifi

The exterior view showcases the cottage beside Lake Rescue, with a clear path leading down to the water. Lush greenery surrounds the property, and a tranquil lake reflects the sky and trees. The space provides direct access to water activities.

4.98 out of 5 average rating, 57 reviews

Ludlow Lake & Ski Cottage - Adventure Awaits!

5 out of 5 average rating, 114 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

The Vermont Farmhouse|Hiking|Dog Trails|Village

4.95 out of 5 average rating, 129 reviews

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Flat in Putney

Minimal organic hideaway inspired by nature

5 out of 5 average rating, 65 reviews

Cabin in Plymouth

Mountain Views, Hot tub, Trails, Pond, BBQ

5 out of 5 average rating, 12 reviews

Ludlow Retreat-Hot Tub, Sauna & Game Room

4.98 out of 5 average rating, 174 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, 287 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

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.