Family-friendly vacation rentals in Killington

4.99 out of 5 average rating, 170 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

Indoor spacesFamilyPets

4.99 out of 5 average rating, 110 reviews

An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.

Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

FamilyIndoor spacesCondition

4.98 out of 5 average rating, 183 reviews

A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.

Treehouse in Hancock

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

FamilyKitchenHeating

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

4.91 out of 5 average rating, 109 reviews

PeeP Hike Golf with Pool and Tennis 2 Bed on Mtn

Come enjoy this peaceful retreat, a warm fire and ski-in trail (depends on snowfall) with beautiful Mountain views! Our cozy 2 bedroom 1 bath is nestled away right on the golf course near Snowshed; Minutes away from ski lifts, restaurants and night life. Enjoy a warm space by the fire after skiing, snowmobiling, tubing and shopping! Shuttle every 30 min weekend & holiday weeks- Common laundry room -free washer/dryer Ski Locker- Pool heated in the summer Enjoy the Beast of the East!

Indoor spacesFamilyHeating

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

4.99 out of 5 average rating, 184 reviews

Alpine Condo - Close to Ski, Golf & Bike

Updated 1-bedroom condo with stylish alpine feel in the heart of Killington! Just minutes from the ski slopes, Bike Park, Adventure Center, golf, hiking, and scenic drives. ⛷️🚴🏻‍♂️🍂 Enjoy Vermont’s spectacular fall foliage, winter adventures, or a relaxing mountain getaway. After a day outdoors, cozy up by the gas fireplace. Sleeps 4 with king bed + queen pullout. Ski Shuttle available weekends (Dec–April) & ski home trail. Pack & Play available upon request. Reg #007718

FamilyKitchenWifi

4.97 out of 5 average rating, 470 reviews

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Indoor spacesFamilyCondition

4.97 out of 5 average rating, 155 reviews

A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.

Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

Indoor spacesKitchenHeating

4.93 out of 5 average rating, 124 reviews

3BR at base of Pico Mountain!

Ski-on/Ski-off!! Our condo is at the base of Pico Mountain and offers amazing views from the private balcony. Enjoy all the benefits of being slope side of Pico Mountain while just 10 minutes away from Killington Resort! Pico Mountain offers 57 trails with 6 lifts and is a family-favorite to avoid some of the weekend crowds at Killington. Less then 1 mile from the Long Trail and Deer Leap overlook hiking trail. Both fantastic must-do hikes when in the area!

FamilyKitchenParks

A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.

4.94 out of 5 average rating, 308 reviews

Vermont Retreat, Dogs Welcome, Pool & Spa

Coffee on the patio. Mountains turning gold. Your dog already halfway down the trail. That’s summer and fall at The Woods. This spacious dog-friendly 2BR sleeps 6 and features a full kitchen, fireplace, private patio, and access to the indoor pool, hot tub, and spa. Minutes from Killington Bike Park, hiking, golf, and restaurants, it’s the perfect home base for Vermont adventures. Bring the crew. Bring the pup. This is the place guests rebook before checkout.

FamilyIndoor spacesSkiing

4.98 out of 5 average rating, 520 reviews

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

Kingsley Grist Mill Waterfall & Private Beach OMG

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 romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

Indoor spacesKitchenPool

4.94 out of 5 average rating, 113 reviews

Apartment in Rutland

Red Rooster Fall Foliage Hub Near Downtown Rutland

Welcome to The Red Rooster, a private second-floor guest suite in a historic 1867 Greek Revival Victorian with ample parking. Located on urban micro-farm, tucked into Rutland's Historic District, enjoy peaceful views and perfect urban convenience. Walk right to downtown dining, Amtrak, and the Paramount Theater! We are minutes from Killington Resort, Pico, the VAST trail, Appalachian Trail, and Lake Bomoseen. Your Green Mountain basecamp awaits.

FamilyKitchenDecor

4.97 out of 5 average rating, 118 reviews

A comfortable living room is presented, featuring two patterned armchairs and a dark sofa. A coffee table occupies the center space, with side tables and lamps positioned strategically. Natural light filters through the windows, while a ceiling fan offers a cooling breeze.

Guesthouse in Plymouth

Quiet Couples Retreat near Killington and Okemo

Clean and comfortable rural guest house in quiet and serene setting on 68 acres of land in Plymouth on Vermont Route 100, a top 10 scenic road in the US. Only 15 minutes from Killington and Okemo and minutes from hiking, lakes, fishing, boating, swimming, and a state beach and boat landing. Historic Woodstock is 15 miles away. Guests must be 21+. Inquiries from guests with no prior reviews on Airbnb will be further screened.

Indoor spacesFamilyRiver

Popular amenities for Killington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.

4.9 out of 5 average rating, 154 reviews

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski

Indoor spacesFamilyCleanliness

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

4.91 out of 5 average rating, 227 reviews

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

FamilyIndoor spacesHeating

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.

4.94 out of 5 average rating, 232 reviews

Newly renovated ski retreat at Killington

FamilyKitchenOutdoor spaces

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.

4.79 out of 5 average rating, 337 reviews

Serene Top Floor Condo (resort style amenities)

Indoor spacesKitchenHiking

A spacious living room features a real wood fireplace with a modern hearth, surrounded by a cozy seating arrangement. A flat-screen television is mounted above the fireplace. Large windows provide natural light and a view of the outdoor balcony, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 111 reviews

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

Indoor spacesFamilySkiing

4.94 out of 5 average rating, 127 reviews

The exterior of a three-level wooden house features a deep orange siding with large windows and a steep metal roof. A spacious wooden deck extends across the front, offering a natural, wooded backdrop. Surrounding landscaping includes a gravel path leading to the entrance.

Home in Killington

Cozy Private House on Killington Mtn - Hottub

Indoor spacesFamilyGrill

4.98 out of 5 average rating, 123 reviews

An exterior view of the home showcases a patio adorned with string lights, providing a warm glow against the backdrop of rolling green hills. The hot tub is visible nearby, adding to the inviting outdoor space perfect for gatherings.

Cabin in Killington

Camp Poe: HotTub/AC/Game Room/6acres/Patio/EVchrgr

Indoor spacesFamilyCheck-in

4.89 out of 5 average rating, 140 reviews

Home in Killington

Golf and Mountain Biking outside the door!

KitchenIndoor spacesGetting around

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 100 reviews

Bright & Cozy Ski-in Condo with Mountain View

FamilyIndoor spacesAmenities

Superhost

4.86 out of 5 average rating, 128 reviews

Ski-In Luxe Chalet • Modern Retreat • 4BR Escape

Indoor spacesKitchenGetting around

4.89 out of 5 average rating, 124 reviews

The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.

Condo in Mendon

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

KitchenFamilySleep quality

Superhost

A cozy living area features a brick fireplace at its center, surrounded by two comfortable armchairs and a wooden coffee table. A Roku Smart TV is positioned next to large glass doors leading to the balcony, while a mirror reflects the warm ambiance. Natural light enhances the wooden accents on the walls.

4.84 out of 5 average rating, 188 reviews

Cozy Condo- Close to Mountain, Ski home trail

FamilyKitchenCleanliness

4.79 out of 5 average rating, 190 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

KitchenIndoor spacesWalkability

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.

4.96 out of 5 average rating, 173 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

FamilyIndoor spacesAccess

Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.

4.87 out of 5 average rating, 127 reviews

Updated large condo across from AT and skiing

Indoor spacesKitchenLocation

4.93 out of 5 average rating, 29 reviews

Apartment in Killington

Skier's Retreat | Hot Tub | Sauna | Free Shuttle

KitchenFamilyNearby

Family-friendly home rentals with air conditioning

4.99 out of 5 average rating, 320 reviews

The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.

Barn in Woodstock

THE LOFT, stunning views from a timber framed barn

KitchenFamilyQuiet

Guest suite in Stockbridge

5.0 out of 5 average rating, 117 reviews

Studio Suite with Vermont Style & Amazing Views

KitchenFamilyRiver

4.98 out of 5 average rating, 174 reviews

Home in Mendon

New Firepit, Great Location, Dog Friendly, Kitchen

FamilyIndoor spacesAmenities

4.84 out of 5 average rating, 332 reviews

A serene outdoor setting features a two-story house surrounded by greenery. A small pond reflects the landscape, while a fire pit is visible nearby. Rustic wooden chairs provide seating, and smoke can be seen rising from the fire, creating a cozy atmosphere in nature.

Home in Goshen

Nature Lover's Paradise

FamilyIndoor spacesWifi

4.9 out of 5 average rating, 180 reviews

A modern wooden structure features numerous large windows that invite natural light. A spacious balcony extends from the upper level, overlooking a snowy landscape. Surrounding trees create a serene environment, complementing the home's rustic aesthetic.

Home in Killington

Deluxe Suite (Mountain Sports Inn)

FamilyKitchenHot tub

5.0 out of 5 average rating, 162 reviews

The exterior of a renovated one-room schoolhouse is presented, set amidst lush green foliage. A vibrant red door stands out against the white walls, while a well-maintained hedge borders the property. Surrounding trees provide a serene backdrop, creating a peaceful atmosphere.

Home in Rutland

One Room School House. No Cleaning Fees!

Indoor spacesFamilyOutdoor spaces

4.93 out of 5 average rating, 408 reviews

Cabin in Poultney

Waterfront Vermont Lake House w/ Panoramic Sauna

KitchenIndoor spacesAmenities