Kid-friendly vacation rentals in Stockbridge

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Stockbridge

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

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Guest favorite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Jan 26 – Feb 2

R2,921 ZAR per night

Superhost

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

R10,121 ZAR per night

Guest favorite

Guest suite in Royalton

4.96 out of 5 average rating, 180 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Jul 23 – 30

R2,238 ZAR per night

Superhost

Chalet in Stockbridge

4.85 out of 5 average rating, 115 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

R2,933 ZAR per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 131 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Aug 10 – 17

R1,883 ZAR per night

Guest favorite

Apartment in Stockbridge

4.88 out of 5 average rating, 160 reviews

Rustic 64 Acre Woodland Haven on a Beautiful River

Peaceful 64 acre secluded retreat located in a forested valley, surrounded by a beautiful river, accessed by a private bridge, with private swimming holes and river beaches. Private full level apartment in a two floor house, with forest views from every window. Perfect for river swimming in Summer, leaf-peeping in the Fall, and winter skiing. Connected to VAST and VASA trails system. Appalachian Trail access. Two miles to the Wild Fern, 7 miles to I-89. 20 minutes from Killington.

Oct 5 – 12

R3,410 ZAR per night

Guest favorite

Apartment in Pittsford

4.99 out of 5 average rating, 118 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike in the warmer weather. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front wheel or 4 wheel drive vehicles with good all season or snow tires required in the winter.

Jul 7 – 14

R2,034 ZAR per night

Guest favorite

Cabin in Randolph

4.95 out of 5 average rating, 193 reviews

Secluded Log Home on 109 Acre Natural Wonderland!

Enjoy our remote, easily accessible, immaculate new log house, set in nature on 109 acres. Pond, woods, fields and trails; with high speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker and many other amenities. Screened in porch. Views from every room! In the heart of the ski corridor. Explore the trails, and the meditation yurt when available!

Aug 11 – 18

R2,818 ZAR per night

Guest favorite

Guest suite in Bethel

4.97 out of 5 average rating, 137 reviews

Two bedroom. Separate enterence.

Please be advised that during winter months you may need to walk up Winterberry lane and our driveway if you do not have an AWD vehicle with good snow tires. Two bedroom apartment in the heart of Vermont. Snowmobile trail located off lane. Snowshoe, hike, or mountain bike from the door. Quiet private location with separate entrance and parking onsite. Ramp to access apartment, with stair free access. Pond, views and located in the center of the state, a great place to start!

Aug 25 – Sep 1

R2,460 ZAR per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 394 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Mar 13 – 20

R2,631 ZAR per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 320 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Dec 18 – 25

R2,680 ZAR per night

Guest favorite

Apartment in Bethel

4.96 out of 5 average rating, 171 reviews

Fred Eddy Farmhouse

You will be renting an apartment in a renovated 1800’s farmhouse. The apartment is newly renovated with all the modern amenities. The place has a lot of charm but that being said the “main house” still needs to be completed. It’s not a brand new house, the exterior of the house has the rustic charm, there are windows waiting to be replaced, in the old farmhouse side I just wanted to make it clear pre-booking!

Nov 21 – 28

R3,029 ZAR per night