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Family-friendly vacation rentals in Castleton

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Castleton

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

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Home in Rutland

4.8 out of 5 average rating, 319 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, 460 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.

Cabin in Castleton

4.97 out of 5 average rating, 110 reviews

Peaceful Cabin Near Lake Bomoseen

Rustic, comfortable cabin in desirable Lake Bomoseen area of central Vermont. Great family or personal escape from the hectic city. Quiet stream wraps around the property with lawn area to relax and play. If looking for a place to 'party' and enjoy loud music, this is not the ideal location for a stay. A great little family beach on the lake is a short walk nearby. For kayakers that want access to Lake Bomoseen, the cabin has deeded access to a private boat ramp 2 minutes down the road.

Cottage in Pawlet

4.96 out of 5 average rating, 127 reviews

Carriage Barn at Indian Hill

Our guest cottage is a lovely converted 1840s-era carriage barn nestled in the heart of the Mettawee Valley in the southwest corner of Vermont. It is decorated with antiques, artworks and an upright piano. Our 65 acres on scenic Indian Hill are available for hiking & snow-shoeing. We have 12 acres frontage on the Mettawee River, rated one of the best for fly fishing in VT. Ready access to many area attractions, from local swimming holes to skiing at nearby Bromley and Stratton mountains.

Guesthouse in Granville

4.9 out of 5 average rating, 839 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. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming 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 recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Home in Leicester

4.97 out of 5 average rating, 154 reviews

Pristine Cottage, Grand Piano, Massage Studio

Meticulously clean, private getaway, custom built home to yourself. Beam ceilings, wood floors, oriental carpets, Alexa, grand piano & lots of art. Complete kitchen, pancake mix & Vt maple syrup. Coffee, teas, orange juice, bagels, cream cheese, granola & fruit. Shower bath with shampoo, conditioners, body wash etc. New private deck, tables & chairs... outside art work. Massage available in log cabin on site $70 Ninja Warrior outside gym with trampoline & slack line

Cabin in Hancock

4.95 out of 5 average rating, 234 reviews

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

Bungalow in Castleton

4.8 out of 5 average rating, 316 reviews

Lake Bomoseen Bungalow

My place is nestled on a private road on Lake Bomoseen in the the Lakes Region of beautiful Vermont. We are within 50 minutes from Killington, Pico, and Okemo mountains. Close to Castleton State University, you’ll love the cozy, private, one room guest cottage that awaits you with your very own lake front sitting area a short distance from the bungalow. Use my kayaks or bring your own; dock space available for small boats. Boat rental is an option at a local marina.

Home in Clarendon

4.96 out of 5 average rating, 263 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!

Cabin in Hancock

4.97 out of 5 average rating, 357 reviews

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

Rental unit in Rutland

4.96 out of 5 average rating, 556 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.

Rental unit in Andover

4.98 out of 5 average rating, 404 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Vacation rentals for every style

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Popular amenities for Castleton family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Plymouth

4.95 out of 5 average rating, 231 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Home in Queensbury

4.99 out of 5 average rating, 158 reviews

Sunset Bay: Amazing waterfront w/ dock on 5 acres!

Home in Lake George

4.83 out of 5 average rating, 315 reviews

Lux 2 br King Suite w Hot Tub in Lake George

Cabin in Londonderry

4.82 out of 5 average rating, 434 reviews

The Honeymoon Barn - hot tub/sauna #1 Airbb S. VT

Condo in Killington

4.78 out of 5 average rating, 286 reviews

Serene Top Floor Condo (resort style amenities)

Chalet in Stockbridge

4.93 out of 5 average rating, 175 reviews

Killington summer winter ski - MTbike -new jacuzzi

Condo in Killington

4.96 out of 5 average rating, 125 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Home in Bolton

4.84 out of 5 average rating, 210 reviews

The Summerwind Lodge

Family- and pet-friendly home rentals

Cabin in North Hudson

4.82 out of 5 average rating, 284 reviews

Schroon River Cabin

Cabin in West Windsor

4.97 out of 5 average rating, 129 reviews

Cowshed Cabin Farm

Cabin in Cavendish

4.97 out of 5 average rating, 143 reviews

The Cozy Little Red Cabin

Cabin in Jamaica

4.89 out of 5 average rating, 364 reviews

Forest Cabin-Swim-Views-Fire Pit-7 min to Stratton

Chalet in Stockbridge

4.85 out of 5 average rating, 131 reviews

Vermont Chalet

Tiny home in Jamaica

4.94 out of 5 average rating, 1,201 reviews

Apple Blossom Cottage: A Tiny House

Guesthouse in Hartland

4.95 out of 5 average rating, 951 reviews

Yurt In The Woods - Private Refuge

Rental unit in Saratoga Springs

4.91 out of 5 average rating, 256 reviews

Cody Farms Private Spacious Apartment - No Cln Fee

Family-friendly home rentals with a pool

Home in Salem

4.98 out of 5 average rating, 185 reviews

Magical Farm Getaway - a must visit!

Guesthouse in Ticonderoga

5 out of 5 average rating, 209 reviews

Chilson Brook Alpacas

Guest suite in Killington

4.95 out of 5 average rating, 139 reviews

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

Home in Granville

4.95 out of 5 average rating, 124 reviews

Epic Views of the Green Mountains

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

4.89 out of 5 average rating, 237 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Condo in Killington

4.78 out of 5 average rating, 163 reviews

Amazing,Ski, Golf, Hike, Bike, Adventures

Condo in Killington

4.86 out of 5 average rating, 112 reviews

Ski in - Near Resort 4 Bedroom

Quick stats about vacation rentals that are family-friendly in Castleton

Total rentals
40 properties
Nightly prices starting at
$150 before taxes and fees
Total number of reviews
1.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore