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Family-Friendly rentals near Okemo Mountain Resort

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Top-rated family-friendly rentals near Okemo Mountain Resort

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Top guest favorite

The rustic cabin features a red exterior with a metal roof, framed by lush greenery. Flower pots with colorful blooms adorn the porch, which includes a small table and chairs. Large windows allow natural light to illuminate the interior.

Cabin in Londonderry

4.94 out of 5 average rating, 348 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

A gently sloping field is depicted, bordered by trees with autumn foliage. A red barn and a white building are visible in the distance, set against a bright blue sky with scattered clouds. The landscape conveys a peaceful rural setting.

Home in Townshend

4.97 out of 5 average rating, 120 reviews

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

A dining area features a wooden table surrounded by a chair and a bench, illuminated by a modern pendant light. Natural light filters through windows, highlighting the warm tones of the log walls and wooden floor, creating a cozy and inviting space.

Cabin in Chester

4.85 out of 5 average rating, 108 reviews

Handmade 3 Bedroom Log Cabin | 5 Min From Skiing

Wake up to brisk mountain air with a cup of coffee and moose in the front yard... This house is a sanctuary, ideal for ski trips, hiking, leaf peeping, wine, beer, and cheese tasting, shopping and sugar house adventures. This is a place to unwind with friends and family. Sit in front of the cavernous fire place and watch the flames twist up the 18ft, handmade, stone hearth. With three private bedrooms, two bathrooms, a futon, and 10ft dining table, this house comfortably sleeps and feeds 8.

A contemporary A-frame house is set against a backdrop of lush greenery. Large windows dominate the facade, reflecting the evening sky. The outdoor seating area is visible, offering a welcoming space for relaxation amidst nature.

Cabin in Jamaica

4.88 out of 5 average rating, 307 reviews

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Top guest favorite

A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.

4.94 out of 5 average rating, 400 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Top guest favorite

A serene outdoor scene captures a home surrounded by vibrant autumn foliage. Wooden steps lead up the hillside, connecting to a spacious deck that overlooks the landscape. A fire pit, encircled by log seating, is nestled among the colorful plants.

Home in Poultney

4.93 out of 5 average rating, 337 reviews

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Top guest favorite

A private Jacuzzi hot tub is positioned on the wooden deck, surrounded by a black railing. The view beyond features a wooded area with colorful autumn foliage, inviting a peaceful outdoor experience.

4.97 out of 5 average rating, 161 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.

A spacious living area features light green walls and vaulted ceilings, highlighted by a large arched window. A comfortable gray sofa is paired with wooden armchairs and a coffee table. A wooden dining table is visible in the foreground, and a cozy fireplace is fitted into the wall.

Condo in Ludlow

4.78 out of 5 average rating, 193 reviews

Okemo Mountain Getaway for Families w/ Pool Access

Perched on Okemo mountain, this spacious condo is the perfect year-round escape for families and groups. With ski-in/ski-out access, a cozy wood-burning fireplace, and a private balcony, it's perfect for any season—whether you're carving the slopes, hiking scenic trails, or enjoying the vibrant fall colors. Take a dip in the seasonal shared pool or unwind in the hot tub. Featuring a fully equipped kitchen, BBQ grill, and all the comforts of home, it's the ideal mountain getaway!

Top guest favorite

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

4.98 out of 5 average rating, 700 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

A custom-built home nestled in a green landscape, featuring a spacious deck with a solar umbrella. Large windows allow natural light to illuminate the interior, and autumn foliage enhances the outdoor scenery. Nearby trees and open grassy areas create a serene environment.

Home in Clarendon

4.95 out of 5 average rating, 300 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Top guest favorite

The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.

Apartment in Rutland

4.96 out of 5 average rating, 619 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

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.

4.95 out of 5 average rating, 817 reviews

Spacious Renovated Barn Apt on 100 acres!

Our unique hideaway is only two miles from many restaurants, cute shops, the gorgeous Buttermilk Falls and Okemo Mountain Resort opening Sunday December 1, 2024 where you can enjoy mountain biking, a ropes course or skiing and riding! Enjoy 100 acres of hiking 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!

Popular amenities for family-friendly rentals near Okemo Mountain Resort

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.

Apartment in Townshend

4.93 out of 5 average rating, 243 reviews

Private Apt. on Farm, Hot Tub with views!

A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.

Home in Plymouth

4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

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, 197 reviews

2 Doors Down - Modern Farmhouse in Downtown Ludlow

A welcoming living area features a large fieldstone fireplace, with a soft couch and several armchairs arranged for comfort. A coffee table sits in the center of the space. Above, warm lighting illuminates an adjacent dining area, enhancing the cozy atmosphere.

Home in Pittsfield

4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

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.

Condo in Ludlow

4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

A rustic living space features wooden beams and warm, ambient lighting. An antique stove serves as a focal point, surrounded by comfortable seating and a wooden table. Shelves filled with various items add character to the cozy atmosphere.

Cabin in Londonderry

4.81 out of 5 average rating, 480 reviews

Stunning Rustic Apple Barn - hot tub & sauna

The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.

Apartment in Londonderry

4.96 out of 5 average rating, 583 reviews

Vermont Getaway Apartment

A spacious living area is highlighted by a stone-clad fireplace, surrounded by a large sectional sofa. Natural light filters through the draped windows, revealing a serene outdoor view. A rustic wooden shelf holds decorative items, and a stack of firewood is neatly arranged beside the fireplace.

Condo in Killington

4.97 out of 5 average rating, 147 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Family- and pet-friendly home rentals

A cozy cabin is nestled among snow-covered trees, featuring a sloped roof blanketed in fresh snow. A woodpile is neatly stacked beside the structure, and a lightly snow-dusted wooden railing surrounds the entrance, enhancing the serene winter landscape.

Cabin in Mount Holly

4.92 out of 5 average rating, 197 reviews

Cozy Vermont Cabin near Okemo.

The exterior of a rustic log cabin is displayed, featuring a metal roof and multiple windows with white trim. Snow covers the ground, enhancing the natural surroundings. A deck can be seen alongside the cabin, providing outdoor space for guests.

Cabin in West Windsor

4.96 out of 5 average rating, 145 reviews

Cowshed Cabin Farm

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, 162 reviews

The Cozy Little Red Cabin

A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.

Apartment in Town of Rockingham

4.82 out of 5 average rating, 188 reviews

Apartment on Main Street

Top guest favorite

A secluded cabin is nestled among trees and foliage during autumn. Vibrant fall leaves cover the ground, and a variety of evergreens provide a natural backdrop. The cabin features a large front porch, allowing for a peaceful connection with the surrounding wilderness.

Cabin in Woodstock

4.96 out of 5 average rating, 202 reviews

Hideaway Cabin by the Stream on 27 Acres

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

4.9 out of 5 average rating, 921 reviews

Moon Valley Country Retreat no clean fee pets yes

The exterior features a classic farmhouse with a blue metal roof and white siding. A welcoming front porch is equipped with rocking chairs, surrounded by lush greenery and a picket fence. The entrance is framed by two large windows on either side.

Home in Grafton

4.95 out of 5 average rating, 155 reviews

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Top guest favorite

The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.

Guesthouse in Hartland

4.95 out of 5 average rating, 997 reviews

Yurt In The Woods - Private Refuge

Family-friendly home rentals with a pool

A serene backyard features a heated saltwater swimming pool, surrounded by lounge chairs and a safety fence. Verdant landscapes and a blue sky provide a tranquil backdrop, while a red barn is visible in the distance, adding to the rural charm.

4.98 out of 5 average rating, 194 reviews

Magical Farm Getaway - a must visit!

An outdoor heated pool is surrounded by a stone patio, furnished with lounge chairs and umbrellas. Lush green grass and neatly trimmed shrubs outline the pool area, complemented by trees and well-maintained landscaping in the background.

Townhouse in Dover

4.96 out of 5 average rating, 149 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

A spacious backyard features a clear swimming pool bordered by a wooden deck. Colorful flowers accent the landscape, and sun loungers invite relaxation. The two-story residence showcases large windows, blending the indoor and outdoor environments, with an umbrella providing shade beside the pool.

Guest suite in Killington

4.95 out of 5 average rating, 148 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

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.

4.91 out of 5 average rating, 101 reviews

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

A clean swimming pool is framed by a white wooden fence, featuring two metallic handrails leading into the water. Nearby, several lounge chairs provide seating options. Lush greenery and trees surround the area, creating an inviting outdoor space.

Condo in Killington

4.8 out of 5 average rating, 107 reviews

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.

Condo in Killington

4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

A dining area is set with a wooden table adorned with plates and glassware, complemented by a stylish chandelier overhead. In the background, a comfortably furnished living area features a sofa and a smart TV, creating a welcoming environment.

Condo in Killington

4.89 out of 5 average rating, 162 reviews

Modern Killington Farmhouse Condo: Close to Resort

An indoor pool area features a large, inviting swimming pool with clear blue water. High ceilings allow natural light to fill the space, while large windows enhance the open feel. Potted plants and wooden accents contribute to a relaxed ambiance.

Condo in Killington

4.97 out of 5 average rating, 146 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Family-friendly home rentals with Wifi

A charming wooden house is surrounded by a snowy landscape, showcasing a large deck and steps leading to the entrance. Snow-covered trees and a clear blue sky enhance the serene setting. The structure features multiple levels, presenting a cozy, inviting exterior.

Cottage in Newfane

4.9 out of 5 average rating, 257 reviews

Ridgeview: Cozy Cottage with a View

A green, grassy area is framed by tall, slender trees. Two benches are positioned on either side, offering a place to sit and admire the expansive view of distant hills and valleys under an overcast sky.

Apartment in Chester

4.89 out of 5 average rating, 502 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Top guest favorite

The exterior of a cottage showcases a white façade and a metal roof, with blue shutters framing the windows. A colorful flower garden features various blooms, including irises and lush greenery, enhancing the welcoming approach to the entrance.

Cottage in Hartland

4.97 out of 5 average rating, 465 reviews

Breeze Hill Cottage

Top guest favorite

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guesthouse in Woodstock

4.98 out of 5 average rating, 250 reviews

Cozy Little Spot (Self Check-in)

Top guest favorite

The kitchen features modern stainless steel appliances, including a Viking stove and ample counter space. Exposed brick and wooden beams create a warm atmosphere. A wood stove is positioned nearby, complemented by a rustic brick floor. Natural light filters through the large windows.

4.99 out of 5 average rating, 219 reviews

Lovely Brick Schoolhouse

The exterior of the tiny timber frame cottage is displayed amidst a colorful autumn landscape. Sunlight streams through the trees, highlighting the grasses and fallen leaves. A gravel path leads to the entrance, surrounded by a peaceful natural setting.

Tiny home in Putney

4.94 out of 5 average rating, 758 reviews

Honeycrisp Cottage - A Tiny Timber Frame

Top guest favorite

A modern chalet is situated among lush greenery, featuring a sloped roof and large windows. A cozy outdoor seating area surrounds a fire pit on a grassy lawn, inviting relaxation in a natural setting. A storage area for firewood is visible beside the structure.

Chalet in Woodstock

4.98 out of 5 average rating, 106 reviews

Falcon House: VT Chalet w/Sauna, Bike to Village

The exterior of the house is framed by lush greenery and trees. A gentle path leads to the front entrance, which is sheltered by a small porch. The metal roof and pastel siding complement the natural surroundings, creating a cozy and inviting facade.

4.95 out of 5 average rating, 345 reviews

Cozy Train Depot in Putney Vermont

Quick stats about family-friendly rentals near Okemo Mountain Resort

Total rentals
220 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
3.2K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
110 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace

Destinations to explore