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Family-friendly holiday rentals in Killington Ski Area

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Top-rated family-friendly rentals in Killington Ski Area

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

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Home

4.87 out of 5 average rating, 137 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Guest favourite

Home

4.8 out of 5 average rating, 334 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.

Guest favourite

Flat

4.87 out of 5 average rating, 124 reviews

New Modern Apartment - Woodstock Village on Mt Peg

One bedroom apartment with private entrance, full kitchen and full bath on lower level of newly built warm modern home located in the village of Woodstock VT, at the edge of Woodstock's Mt Peg Town Forest. Able to accommodate a maximum of two adults and one or two younger children, this apartment sits in a serenely peaceful location at the edge of extensive hiking, mountain biking and nordic ski trails and several minutes walk up a steep hill, above the beautiful Village of Woodstock Vermont.

Apartment

4.89 out of 5 average rating, 157 reviews

Modern Killington Farmhouse Condo: Close to Resort

Welcome to our condo in picturesque Killington. This 2RM/2BA modern farmhouse-style unit features an open kitchen, stainless appliances, island, dining area, living room w/ smart TV, gas fireplace, sofa bed, queen bed, easy chair & amazing tile shower w/ body jets. The primary bedroom has ensuite bathroom, TV, flexible king bed, AC & washer/dryer. Reclaimed barn board finishes & sliding barn doors add rustic charm. Plus a summer pool! Book now for modern comfort & rustic charm in Killington!

Guest favourite

Home

4.86 out of 5 average rating, 109 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.

Home

4.9 out of 5 average rating, 291 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.

Apartment

4.78 out of 5 average rating, 170 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Killington has become a wonderful 4 season resort area that satisfies many tastes. You can hike, play golf ,swim, bike, ski-snowboard, or just lay back and enjoy the surroundings. You can go to the Killington website to find out what is happening. Please go to the Killington website to get complete information before you go. There is also a Mountain Green website that will let you know which amenities are available during your stay. mountaingreen.com

Guest favourite

Home

4.93 out of 5 average rating, 138 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. Water activities 2 kayaks 1 - 4 person paddle boat

Guest favourite

Flat

4.89 out of 5 average rating, 495 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway living room at one end with 2 couches, desk and TV Other end is full compact kitchen with dishwasher, stove and over, full size refrigerator, coffee maker and microwave.

Guest favourite

Home

4.84 out of 5 average rating, 144 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

5 miles to Okemo Mountain, this private and spacious setting offers access to hiking, skiing, snowmobiling or cycling. After hours of fun, relax by the fireplace, soak in the hot tub, cook a well-deserved meal or plan an evening out. A perfect location for families or groups of friends. We have implemented the infection control plan recommended by the CDC. See “Other things to note” for our cleaning details.

Guest favourite

Home

4.97 out of 5 average rating, 154 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Much of the house newly renovated in the Fall, 2023. Relax in this 3-level (1700+ sq. ft) ski chalet that's a 4 min drive to the Okemo Mountain Resort and the center of town, and a 6 min drive to Jackson Gore. Take in the 180-degree views of your wooded backyard with floor-to-ceiling windows and unwind in front of the fireplace or relax in the Jacuzzi hot tub in your private oasis on the mountain.

Guest favourite

Cottage

4.95 out of 5 average rating, 146 reviews

The Cottage on Westerdale Road

This charming house is close to the quaint Village of Woodstock, restaurants and dining, and family-friendly activities. You’ll love my place because of the ambiance, the quality furnishings, air conditioning, the outdoors space, the quiet neighborhood, the comfy beds, and the light. My place is good for couples, business travelers, families (with kids). Sorry, we can no longer welcome pets.

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Popular amenities for Killington Ski Area family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Guest house

4.96 out of 5 average rating, 253 reviews

Macintosh Hill Farm

Guest favourite

Chalet

4.83 out of 5 average rating, 242 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Guest favourite

Chalet

4.95 out of 5 average rating, 120 reviews

Okemo Ski Chalet with Hot Tub

Apartment

5 out of 5 average rating, 11 reviews

3 Bedroom Castle Town Home

Home

4.84 out of 5 average rating, 231 reviews

Killington area home - 4-seasons & hot tub

Chalet

4.92 out of 5 average rating, 177 reviews

Killington ski house winter MTbike -new jacuzzi

Guest favourite

Chalet

4.87 out of 5 average rating, 244 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Guest favourite

Cabin

5 out of 5 average rating, 102 reviews

#7 - Hemlock Hideaway Cabin

Family- and pet-friendly home rentals

Cabin

4.95 out of 5 average rating, 150 reviews

The Cozy Little Red Cabin

Flat

4.79 out of 5 average rating, 183 reviews

Downtown Middlebury 3 BR Home - Walk Everywhere!

Guest favourite

Cabin

4.95 out of 5 average rating, 198 reviews

Hideaway Cabin by the Stream on 27 Acres

Guest favourite

Cabin

4.95 out of 5 average rating, 242 reviews

Hancock hideaway

Guest favourite

Home

4.83 out of 5 average rating, 283 reviews

Nature Lover's Paradise

Home

4.78 out of 5 average rating, 104 reviews

Sugarbush 1880s Farmhouse - With Scenic Views 5/2

Guest favourite

Home

4.98 out of 5 average rating, 202 reviews

The Guest House at Sky Hollow

Guest favourite

Cabin

4.93 out of 5 average rating, 143 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

Family-friendly home rentals with a pool

Guest favourite

Home

4.96 out of 5 average rating, 135 reviews

Epic Views of the Green Mountains

Guest favourite

Guest suite

4.95 out of 5 average rating, 141 reviews

Cozy, private, spacious, 3 bedrooms, 5 mi to K Rd.

Guest favourite

Guest house

4.9 out of 5 average rating, 869 reviews

Moon Valley Country Retreat no clean fee pets yes

Apartment

4.8 out of 5 average rating, 103 reviews

Ski Mountain Escape: 3 Bdrm, Ski In & Bus In

Guest favourite

Apartment

4.82 out of 5 average rating, 256 reviews

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

Apartment

4.78 out of 5 average rating, 294 reviews

Serene Top Floor Condo (resort style amenities)

Guest favourite

Apartment

4.96 out of 5 average rating, 134 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Guest favourite

Apartment

4.93 out of 5 average rating, 430 reviews

Ski in n out Pico 1 bedroom 1 nite Ok free shuttle

Destinations to explore