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Family-friendly vacation rentals in Rutland County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Rutland County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A custom-built chalet is nestled among lush greenery, showcasing a unique A-frame design. The exterior features stone columns and wooden balcony railings. An American flag can be seen hanging, adding a touch of character to the inviting setting.

Chalet in Wells

4.9 out of 5 average rating, 143 reviews

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

Base rate includes 6 guests. We welcome events reunions, weddings and film studios! Nearby lake, golf, hiking! Your Private 3600 sq ft home+18 acres has an awesome view! Authentic Chalet sleeps 12 (three bedrooms and baths, two queen sofas, daybed). Summer HVAC, Artisan fireplace, oven, Induction cooktop, stocked kitchen, ROKU HDTV, fast Wi-Fi, FirePit Patio. We supply linens / bath towels for beds and baths. As an option, a Private separate 350 sq ft studio office—5-star by work-from-homers.

The exterior of a two-story white house is pictured, featuring a red front door and black shutters on the windows. A well-maintained lawn with green grass and a tree is visible in the front yard, presenting a welcoming appearance.

Home in Rutland

4.81 out of 5 average rating, 349 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

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, 329 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 pathway of stone steps meanders through a lush green lawn, flanked by vibrant red geraniums in terracotta pots. Tall trees provide shade, creating a serene atmosphere, while a wooden bench invites relaxation amidst the surrounding nature.

Apartment in Dorset

4.99 out of 5 average rating, 188 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

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, 908 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

The charming guest cottage, with a light-coloured exterior and a metal roof, is surrounded by vibrant autumn foliage and wildflowers. A serene landscape of rolling hills enhances the rural setting, inviting outdoor exploration and relaxation.

Cottage in Pawlet

4.96 out of 5 average rating, 130 reviews

Carriage Barn at Indian Hill

Our guest cottage is a lovely converted 1840s-era carriage barn nestled in the heart of the Mettawee Valley in the southwest corner of Vermont. It is decorated with antiques, artworks and an upright piano. Our 65 acres on scenic Indian Hill are available for hiking & snow-shoeing. We have 12 acres frontage on the Mettawee River, rated one of the best for fly fishing in VT. Ready access to many area attractions, from local swimming holes to skiing at nearby Bromley and Stratton mountains.

The serene lake reflects vibrant fall foliage on the surrounding trees, creating a warm tapestry of orange and yellow. Soft gray clouds drift above, adding depth to the autumn landscape. A small boat is anchored nearby, contributing to the tranquil scene.

Home in Whitehall

4.93 out of 5 average rating, 142 reviews

Lakefront A-Frame Home Emerald Lake, NY

A Frame style home with 100 + feet of lake frontage. 2 bedroom plus a loft bedroom with 2 twin beds. 1 and 1/2 baths and large open basement A-frame style home on a small, quiet lake in upstate NY in the town of Hampton/Whitehall, NY (not on Lake George), 5 miles from the VT border, 33 miles from Lake George village, with a screened in porch, a large deck, and a grill provided (new grill 2025). Water activities 4 kayaks 1 - 4 person paddle boat

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

4.96 out of 5 average rating, 296 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, 610 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.

Top guest favorite

The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.

Castle in Clarendon

4.98 out of 5 average rating, 468 reviews

Kingsley Grist Mill, w/ Private Beach & Waterfall

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the history, the romance, the breakfast, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. Come make history with us ! Near Killington & Okemo Mtns.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Villas

Luxurious estates for the ultimate escape

Houses

A space thats all yours, with room for everyone

Popular amenities for Rutland County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A secluded chalet is surrounded by snow-covered trees, showcasing its wrap-around deck. The winter landscape features undisturbed snow blanketing the ground, while blue skies peek through scattered clouds above.

Chalet in Plymouth

4.75 out of 5 average rating, 215 reviews

5BR Chalet in Historic Town bet Killington & Okemo

A cozy living space features a warm wood-burning fireplace, with flames gently glowing behind a glass screen. A soft beige leather sofa is complemented by a bright red decorative pillow. A standing lamp provides soft illumination next to the fireplace, enhancing the inviting ambiance.

Condo in Killington

4.92 out of 5 average rating, 106 reviews

Right at Killington !

A spacious living area features vaulted wooden ceilings with exposed beams, allowing natural light to fill the room. Comfortable couches are arranged around a central coffee table, with a large television set against the wall. Light-colored curtains frame the windows, enhancing the inviting ambiance.

Chalet in Killington

4.84 out of 5 average rating, 251 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.

Condo in Killington

4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

A rustic ski chalet is nestled among snow-covered trees, with a sloping driveway leading to the entrance. The building showcases a wooden deck and vibrant blue exterior, surrounded by a serene winter landscape.

Chalet in Ludlow

4.82 out of 5 average rating, 76 reviews

Mountain Chalet + HOT TUB

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

Condo in Killington

4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.

Condo in Killington

4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

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, 160 reviews

Ski Chalet with Hot Tub on Okemo Mountain

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, 196 reviews

Cozy Vermont Cabin near Okemo.

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 contemporary ski house is featured, set against a snowy landscape. The structure showcases large glass windows and a spacious deck, elevated on stilts. Surrounding trees and a light dusting of snow enhance the serene atmosphere of the property, inviting a cozy retreat.

Chalet in Ludlow

4.95 out of 5 average rating, 129 reviews

Okemo Ski Chalet with Hot Tub

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 log cabin is nestled in a lush green landscape, surrounded by mature trees. The structure features a welcoming front porch with seating and a sloping roof. A spacious grassy area lies in front, providing an open space for relaxation.

4.89 out of 5 average rating, 298 reviews

Mountain treasures await.

An open living space features a bright red sofa with decorative pillows, complemented by a warm wood dining area with stools. The kitchen, equipped with stainless steel appliances, is visible in the background. Soft lighting creates a welcoming ambiance throughout the suite.

Condo in Killington

4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

The exterior of the upper unit duplex is surrounded by snow, showcasing a wooden deck with a railing and steps leading to the entrance. A prominent stone chimney rises from the roof, and large windows provide a view of the surrounding forest.

Chalet in Stockbridge

4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

A warm living space is crafted with wooden paneling and large windows that provide natural light. Comfortable seating includes a leather sofa and patterned armchairs, arranged around a wooden coffee table. Soft lighting is provided by lamps, enhancing the cozy atmosphere.

Chalet in Killington

4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Family-friendly home rentals with a pool

A well-maintained outdoor pool area features a rectangular swimming pool surrounded by a paved patio. Red umbrellas provide shade over several lounge chairs, creating a relaxed environment. A small pool house stands nearby, with trees and greenery framing the scene.

Condo in Killington

4.77 out of 5 average rating, 272 reviews

Come to Killington this summer!

An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.

Condo in Killington

4.75 out of 5 average rating, 92 reviews

Low Summer Rates*

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, 145 reviews

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

A spacious room features two queen beds adorned with vibrant patterned comforters. A flat-screen TV is mounted on the wall. A window allows natural light to fill the space, while an air conditioning unit is positioned nearby. A wooden dresser and lamps add functional touches.

Condo in Killington

4.59 out of 5 average rating, 100 reviews

NEW Killington Studio: Great Location! Comfy. 431

Condo in Killington

4.78 out of 5 average rating, 18 reviews

Whiffletree base of Killington outdoor 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, 98 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

Condo in Killington

4.85 out of 5 average rating, 26 reviews

Spacious 4-Bedroom Condo Near Slopes- D8

Destinations to explore