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Family-friendly vacation rentals in Stockbridge

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Stockbridge

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

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Chalet in Stockbridge

4.93 out of 5 average rating, 168 reviews

Killington spring ski - MTbike -new jacuzzi

Killington Ski Area with access to snowmobile and mountain biking trails. This is a 3 bedroom, 2 bath upper unit duplex. with outdoor Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events too Fantastic unit check our review

Feb 18 – 25

G$112,041 GYD per night

Guesthouse in Woodstock

4.98 out of 5 average rating, 209 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Jan 29 – Feb 5

G$32,812 GYD per night

Cottage in Hartland

4.97 out of 5 average rating, 420 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Apr 21 – 28

G$25,636 GYD per night

Chalet in Stockbridge

4.85 out of 5 average rating, 114 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Aug 24 – 31

G$32,438 GYD per night

Home in Barnard

4.92 out of 5 average rating, 141 reviews

Cozy 2bd, Tennis Court, Steps to Lake, on 6 acres

This 2nd floor space is great for small groups and couples. All wood interior space has been newly updated with modern appliances, handmade slab countertops, and cozy furniture. Directly across from Silver Lake and the Barnard General Store, with 6 parklike acres including a tennis court (with pickle ball)! Easy to find, minutes from Woodstock, VT. and award-winning dining, just 3 minutes to Silver Lake State Park, and just a few miles to multiple access points of the Appalachian Trail.

Mar 10 – 17

G$38,064 GYD per night

Guest suite in Royalton

4.96 out of 5 average rating, 167 reviews

Bluestone Farm

Bluestone Farm is a private second story guest suite with all the amenities. High ceilings, quiet, on a Vermont back road with 70 plus acres of land and a pond. You have a full working kitchen; private bathroom with large walk in shower; living room, and private bedroom with a queensize mattress. Nearby to Vermont Law School, 40 minutes to Ben and Jerry's, Woodstock, and Montpelier. 2 miles from Worthy Burger and a quick ride to Interstate 89 for many other Vermont attractions.

Jul 24 – 31

G$24,423 GYD per night

Cabin in Hancock

4.95 out of 5 average rating, 221 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.

May 10 – 17

G$30,543 GYD per night

Home in Rochester

4.97 out of 5 average rating, 182 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Aug 22 – 29

G$33,721 GYD per night

Cabin in Hancock

4.97 out of 5 average rating, 343 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.

Apr 10 – 17

G$34,569 GYD per night

Apartment in Rutland

4.96 out of 5 average rating, 525 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.

Nov 18 – 25

G$20,709 GYD per night

Home in Middlebury

4.99 out of 5 average rating, 355 reviews

Nice one bedroom cottage

Located at the foot of the Green Mountains, a short walk to the Waybury Pub, nearby hiking, fishing and skiing. 4 miles to heart of Middlebury. Full kitchen, living room, bedroom(queen bed) and bathroom with stand up shower. ethernet connection/cable tv/washer-dryer/ac/ns

Nov 6 – 13

G$27,882 GYD per night

Cabin in Leicester

4.98 out of 5 average rating, 713 reviews

Log Cabin Getaway near Middlebury and Green Mtns

Located at the junction of the Green Mountains and the Champlain Valley, this quiet space sits on 70 forested acres. Enjoy nature in this free-standing secluded space and discover what Addison County has to offer from an easy to access location.

Jan 7 – 14

G$26,282 GYD per night

Vacation rentals for every style

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Popular amenities for Stockbridge family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Pittsfield

4.83 out of 5 average rating, 221 reviews

Killington area home - 4-seasons & hot tub

Nov 5 – 12

G$52,601 GYD per night

Yurt in Randolph

4.96 out of 5 average rating, 386 reviews

4 Season Lower Yurt Stay on VT Homestead

Mar 25 – Apr 1

G$14,472 GYD per night

Condo in Killington

4.77 out of 5 average rating, 283 reviews

Serene Killington Condo (resort style amenities)

Jul 29 – Aug 5

G$30,026 GYD per night

Chalet in Killington

4.9 out of 5 average rating, 159 reviews

Close to Mountain and walk to restaurants!

Jul 1 – 8

G$49,019 GYD per night

Loft in Monroe

4.94 out of 5 average rating, 194 reviews

The Loft at River's Edge w/hot tub!

Oct 31 – Nov 7

G$29,098 GYD per night

Chalet in Killington

4.87 out of 5 average rating, 228 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

Oct 15 – 22

G$106,589 GYD per night

Home in Killington

4.88 out of 5 average rating, 215 reviews

Tanglewood Vista Ski Home: Close|Hot Tub|Sauna|BBQ

May 19 – 26

G$89,205 GYD per night

Chalet in Killington

5.0 out of 5 average rating, 117 reviews

Luxury, AC, 6 BR, 12 Beds, 3 Bath, Hot Tub, Yard

Nov 2 – 9

G$218,721 GYD per night

Family- and pet-friendly home rentals

Cabin in Woodstock

4.96 out of 5 average rating, 191 reviews

Cabin by the Stream on 27 Acres

Mar 23 – 30

G$45,594 GYD per night

Guesthouse in Hartland

4.95 out of 5 average rating, 914 reviews

Yurt In The Woods - Private Refuge

Mar 30 – Apr 6

G$30,503 GYD per night

Home in Rochester

4.9 out of 5 average rating, 282 reviews

Mountain Home ready for you!

Sep 17 – 24

G$59,971 GYD per night

Guesthouse in Norwich

4.93 out of 5 average rating, 171 reviews

Vermont Log Guest Home-Close to Dartmouth

Aug 30 – Sep 6

G$39,071 GYD per night

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

The Barn at North Orchard, Near Middlebury

Jan 1 – 8

G$25,891 GYD per night

Guesthouse in Springfield

4.86 out of 5 average rating, 322 reviews

Connecticut River-Cozy Cottage

Jan 28 – Feb 4

G$19,066 GYD per night

Guesthouse in Granville

4.9 out of 5 average rating, 785 reviews

Moon Valley Country Retreat no clean fee pets yes

Sep 20 – 27

G$22,129 GYD per night

Guesthouse in Groton

4.98 out of 5 average rating, 246 reviews

Groton Forest Retreat

Dec 26 – Jan 2

G$24,349 GYD per night

Family-friendly home rentals with a pool

Condo in Killington

4.92 out of 5 average rating, 392 reviews

April open 1 bedroom 1 night Ok Free shuttle

Oct 10 – 17

G$33,897 GYD per night

Home in Granville

4.95 out of 5 average rating, 107 reviews

Epic Views of the Green Mountains

Oct 26 – Nov 2

G$41,274 GYD per night

Guest suite in Killington

4.95 out of 5 average rating, 139 reviews

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

Nov 6 – 13

G$48,853 GYD per night

Condo in Killington

4.82 out of 5 average rating, 250 reviews

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

Jun 28 – Jul 5

G$46,887 GYD per night

Guesthouse in Ticonderoga

4.99 out of 5 average rating, 197 reviews

Chilson Brook Alpacas

Nov 15 – 22

G$67,385 GYD per night

Guest suite in Ryegate

4.91 out of 5 average rating, 211 reviews

Secluded Paradise on the Connecticut River, VT

May 16 – 23

G$39,500 GYD per night

Apartment in Barre

4.94 out of 5 average rating, 156 reviews

Relax in Recreation Paradise!

Sep 26 – Oct 3

G$32,000 GYD per night

Cabin in Bridport

4.92 out of 5 average rating, 133 reviews

Champlain Valley Alpacas

Oct 16 – 23

G$35,746 GYD per night

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

Total rentals
80 properties
Wifi availability
80 properties include access to wifi
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Total number of reviews
3.4K reviews
Nightly prices starting at
G$22,971 GYD before taxes and fees

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