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Family-friendly vacation rentals in Killington Ski Area

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Guest favorite
A charming cottage is nestled on a grassy knoll, surrounded by trees and wildflowers. The front porch welcomes visitors, while a gravel driveway leads up to the entrance. Bright blue skies enhance the serene outdoor setting.
Cottage in Chester
4.91 out of 5 average rating, 162 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guest favorite
A spacious living room features a textured red carpet and a large beige sectional sofa, complemented by a wooden coffee table. A stone fireplace is situated against one wall, with large windows providing views of the surrounding greenery. Decorative plants and artwork enhance the inviting space.
Home in Weston
4.87 out of 5 average rating, 114 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Guest favorite
A spacious deck features wooden flooring and railing, surrounded by trees. Two wooden lounge chairs face a breathtaking view of the Green Mountains, providing an open space to relax and enjoy the natural scenery.
Home in Rochester
4.91 out of 5 average rating, 295 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Killington Ski Area family-friendly rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly home rentals with a hot tub

Guest favorite
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!

Top guest favorite
A cozy sleeping area is featured with a spacious bed adorned with soft pillows. Natural light filters through sheer curtains, illuminating warm wooden walls. A small TV and a decorative chair provide additional comfort, while a touch of greenery enhances the inviting atmosphere.
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

Guest favorite
A private hot tub is illuminated with soft blue lights, creating a relaxing atmosphere. The hot tub features multiple jets and is surrounded by wooden walls and a partially covered area, ensuring privacy. Warm ambient lighting enhances the tranquil setting, inviting relaxation.
Chalet in Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Guest favorite
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
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

Superhost
Home in Pittsfield
4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

Guest favorite
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

Superhost
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.
Home in Cavendish
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

Guest favorite
A well-lit outdoor Jacuzzi features soothing water jets, creating a relaxing ambiance. The water is illuminated with soft lights, enhancing the tranquil setting. Visible edges and seating areas allow for comfortable relaxation. Surrounding space remains dark, emphasizing the warm glow of the Jacuzzi.
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

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Family- and pet-friendly home rentals

Top guest favorite
Cabin in Corinth
4.99 out of 5 average rating, 240 reviews

Skip's Place

Superhost
A vibrant purple sofa is complemented by a textured gray throw pillow and a colorful patterned pillow. A wooden coffee table features a decorative tray with a plant and a game, while a patterned rug and lamp add detail to the cozy living area.
Apartment in Middlebury
4.79 out of 5 average rating, 192 reviews

Downtown Middlebury 3 BR Home - Walk Everywhere!

Guest favorite
The cabin's exterior showcases natural wood siding and a metal roof. Large windows allow glimpses of a cozy interior, framed by colorful autumn leaves. The entrance is adorned with potted plants, enhancing the tranquil woodland setting.
Cabin in Woodstock
4.95 out of 5 average rating, 198 reviews

Hideaway Cabin by the Stream on 27 Acres

Superhost
The historic farmhouse features a white exterior with a gabled roof, surrounded by lush greenery. A large tree provides shade in the front yard, and flower gardens can be seen along the stone pathway leading to the porch, which has seating for relaxation.
Apartment in Taftsville
4.79 out of 5 average rating, 177 reviews

Quiet Vermont Farmhouse

Guest favorite
A comfortable living area features a warm-toned wooden floor, two armchairs, and a black swivel chair. A decorative rug adds color to the space, which is illuminated by natural light streaming through large windows. A fireplace and wall-mounted TV complete the cozy ambiance.
Home in Goshen
4.84 out of 5 average rating, 285 reviews

Nature Lover's Paradise

Guest favorite
Home in Rochester
4.98 out of 5 average rating, 203 reviews

The Guest House at Sky Hollow

Superhost
The view showcases a rustic cottage nestled among trees along the lake. A wooden dock extends from the rocky shoreline, featuring a ladder for easy water access. The cabin's light yellow exterior complements the natural surroundings, providing a serene escape by the water.
Cottage in Marlow
4.89 out of 5 average rating, 100 reviews

Sunapee area lakeside cottages trio on Sand Pond

Top guest favorite
Chalet in Wells
4.9 out of 5 average rating, 143 reviews

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

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Family-friendly home rentals with a pool

Top guest favorite
A clear blue pool is surrounded by a stone patio and lush green landscaping. Two lounge chairs are positioned nearby. A flagpole is visible in the background, and a hanging planter adds a touch of color.
Guesthouse in Ticonderoga
5 out of 5 average rating, 210 reviews

Chilson Brook Alpacas

Guest favorite
Guest suite in Killington
4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

Guest favorite
A swimming pool is surrounded by lush greenery, inviting relaxation and enjoyment. The clear blue water reflects the surrounding landscape, providing a refreshing appeal. A person is seen in the water, engaged with a floating device, highlighting the leisure activities available at the property.
Guesthouse in Granville
4.9 out of 5 average rating, 894 reviews

Moon Valley Country Retreat no clean fee pets yes

Superhost
A tennis court is set against a backdrop of lush trees and greenery. The court features a smooth, hard surface with clear white lines marking the boundaries. A net stands in the center, ready for play.
Condo in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

Superhost
An indoor swimming pool is depicted with clear blue water, featuring multiple lanes marked by buoy lines. Surrounding areas include seating and wood-paneled walls, providing a spacious and inviting atmosphere for relaxation and recreation.
Condo in Killington
4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

Superhost
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, 307 reviews

Serene Top Floor Condo (resort style amenities)

Superhost
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

Guest favorite
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, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

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