
Family-friendly holiday rentals in Killington
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Killington
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Stylish Vermont Cabin | Views · Trails · Luxe
Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

The Barnbrook House
Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Pool and Spa area closed May 4 to May 15 for annual Maintenance

Tiny Vermont Cabin!
Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

Waterfront Vermont Lake House w/ Panoramic Sauna
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

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

Cozy Condo - AC & Pool. Close to Golf & Bike
Comfortable 1-bedroom Whiffletree condo with air conditioning & pool —minutes from Killington Resort, golf course and access road. Fully stocked with essentials and includes a locker for your gear. Relax and enjoy the onsite outdoor pool (Open Memorial Day - Labor Day). Easy access to summer fun and scenic Vermont trails! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $25 per stay. Killington Reg #004858

THE LOFT, stunning views from a timber framed barn
Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

New Firepit, Great Location, Dog Friendly, Kitchen
Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

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.

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.

Steps to Golf!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!
Popular amenities for Killington family-friendly rentals
Family-friendly home rentals with a hot tub

~The ClubHaus~

Cozy Bow House Perched in Trees w/ Hot Tub & View

Prime Killington Proximity | Ski, Sauna, & Soak!

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Dog heavenly! Private, beautiful and relaxing.

Scandinavian design Chalet hiking trail + hot tub

Newly Renovated, Hot tub, 2min to Killington lift

Large Chalet; Sauna, Hot Tub; Walk to Trail
Family- and pet-friendly home rentals

Cabin on the Hill

The Owl’s Nest in Landgrove

Treehut - Secluded Treehouse in the Forest

Mountain Getaway Pet friendly

Hideaway Cabin by the Stream on 27 Acres

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Vermont Chalet

100 Acres Views & Creek near Woodstock/Killington
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Ranch at Mendon Mt Orchards

Moon Valley Country Retreat no clean fee pets yes

Lower Yurt Stay on VT Homestead

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Still skiing Deal Cozy 2 Bedroom .2 mi to lift

Luxe Trailside Ski On/Off. Next to hot tub
When is the best time to visit Killington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $682 SGD | $738 SGD | $507 SGD | $358 SGD | $322 SGD | $311 SGD | $313 SGD | $303 SGD | $311 SGD | $333 SGD | $350 SGD | $571 SGD |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are family-friendly in Killington

Total holiday rentals
Explore 830 holiday rentals in Killington

Nightly prices starting at
Killington holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 28,300 verified reviews to help you choose

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Holiday rentals with a pool
330 properties feature pools

Rentals with dedicated workspaces
330 properties have a dedicated workspace

Wifi availability
830 of Killington holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Killington rentals

4.8 Average rating
Killington stays are highly rated by guests – averaging 4.8 out of 5!
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- House rentals Killington
- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Dartmouth College
- Middlebury College
- Montshire Museum of Science
- Adirondack Extreme Adventure Course
- Emerald Lake State Park
- Mount Sunapee Resort
- Trout Lake
- Southern Vermont Arts Center
- Warren Falls
- Camp Plymouth State Park
- Things to do Killington
- Food and drink Killington
- Things to do Rutland County
- Food and drink Rutland County
- Things to do Vermont
- Nature and outdoors Vermont
- Food and drink Vermont
- Things to do United States
- Food and drink United States
- Wellness United States
- Art and culture United States
- Tours United States
- Entertainment United States
- Nature and outdoors United States
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