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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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Bungalow in Castleton

4.79 out of 5 average rating, 321 reviews

Lake Bomoseen Bungalow

My place is nestled on a private road on Lake Bomoseen in beautiful VT. 50 minutes from Killington, Pico, and Okemo Mtns and close to Castleton University. You’ll love the cozy, one room guest cottage that awaits you. Although my house sits between the cottage and the lake front, the bungalow still offers beautiful lake views with a lake front patio area 50 ft down the driveway. Use my kayaks or bring your own, dock space available for small boats. Boat rental available at a local marina.

Home in Rutland

4.8 out of 5 average rating, 324 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.

Castle in Clarendon

4.98 out of 5 average rating, 464 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

America's only original Grist Mill & Covered Bridge residence, as seen on HGTV's "You Live in What?", (Se.2. ep.1) & worldwide on the Netflix travel series "World's Most Amazing Vacation Rentals" (Se. 2, ep 7). Join us for our 10th season as central Vermont's iconic adult getaway featuring private beach on Vermont's warmest river with tethered, relaxing, float tubes & two private decks overlooking Mill River's secluded waterfall. Come make history with us ! Near Killington & Okemo Mtns.

Home in Poultney

4.93 out of 5 average rating, 300 reviews

Waterfront VT Lake House with Breathtaking Views!

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

Guesthouse in Granville

4.9 out of 5 average rating, 854 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.

Condo in Killington

4.78 out of 5 average rating, 287 reviews

Serene Top Floor Condo (resort style amenities)

Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it! We also have discounted winter lift tickets.

Home in Mount Tabor

4.98 out of 5 average rating, 242 reviews

Cow Barn Lodge

Our home is located in MT. Tabor, Vermont, just off of Route 7, in a country setting with beautiful Mountain views of the Green Mountain National Forest, Dorset and Danby Mountains. The house is an old barn converted into a beautiful spacious home, on 4 acres. Snowmobiling from our place, plus 4 major ski areas less than 30 miles away. Hiking, fishing, swimming, golfing, and the Equestrian horse show are all nearby. as well as shopping in nearby Manchester and Rutland Vermont.

Home in Plymouth

4.95 out of 5 average rating, 237 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Home in Clarendon

4.96 out of 5 average rating, 270 reviews

Custom 2BR Vacation Retreat in Killington Valley!

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!

Rental unit in Rutland

4.96 out of 5 average rating, 570 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, 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.

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

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Popular amenities for Rutland County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Chalet in Plymouth

4.75 out of 5 average rating, 200 reviews

5BR Chalet in Historic Town bet Killington & Okemo

Chalet in Killington

4.83 out of 5 average rating, 235 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

Home in Killington

4.96 out of 5 average rating, 72 reviews

*Killington Rendezvous House-Timber Frame-HotTub*

Chalet in Stockbridge

4.93 out of 5 average rating, 175 reviews

Killington ski house winter MTbike -new jacuzzi

Condo in Killington

4.96 out of 5 average rating, 128 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Home in Ludlow

4.97 out of 5 average rating, 151 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Condo in Killington

4.78 out of 5 average rating, 163 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Condo in Killington

4.79 out of 5 average rating, 108 reviews

Killington Escape 2 Story 2BR 2BA Main Building

Family- and pet-friendly home rentals

Home in Killington

4.89 out of 5 average rating, 282 reviews

25 Rocky Ridge Road: Ski Home for Groups. Lift Tix

Cabin in Mount Holly

4.91 out of 5 average rating, 186 reviews

Cozy Vermont Cabin near Okemo.

Rental unit in Ludlow

4.92 out of 5 average rating, 262 reviews

Okemo Vermont Getaway

Chalet in Ludlow

4.95 out of 5 average rating, 118 reviews

Okemo Ski Chalet with Hot Tub

Home in Pittsfield

4.84 out of 5 average rating, 227 reviews

Killington area home - 4-seasons & hot tub

Cabin in Danby

4.89 out of 5 average rating, 288 reviews

Great Cabin available to Dec 15th 145.00

Chalet in Killington

4.87 out of 5 average rating, 242 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Loft in Ludlow

4.95 out of 5 average rating, 774 reviews

Spacious Renovated Barn Apt on 100 acres!

Family-friendly home rentals with a pool

Condo in Mendon

4.68 out of 5 average rating, 133 reviews

Killington/Pico Condo, Cozy Family/Friend Getaway

Condo in Killington

4.74 out of 5 average rating, 84 reviews

2 Bedroom 2 Bath Condo at the Base of Killington

Guest suite in Killington

4.95 out of 5 average rating, 139 reviews

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

Condo in Killington

4.74 out of 5 average rating, 65 reviews

Killington Vermont Luxury 2 bed condo

Condo in Killington

4.93 out of 5 average rating, 88 reviews

Cozy 1-bed, Mountain Green Resort - Killington, VT

Home in Ludlow

4.92 out of 5 average rating, 89 reviews

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

Condo in Killington

4.82 out of 5 average rating, 251 reviews

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

Condo in Killington

4.93 out of 5 average rating, 82 reviews

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

Destinations to explore