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Family-friendly holiday 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

3–10 Feb

₹44,751 per night

Guest favourite

Guest house in Woodstock

4.98 out of 5 average rating, 206 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.

11–18 Dec

₹13,133 per night

Guest favourite

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!

17–24 Nov

₹10,239 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.

2–9 Oct

₹13,103 per night

Guest favourite

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.

18–25 Jan

₹15,069 per night

Guest favourite

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.

1–8 May

₹8,900 per night

Guest favourite

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.

3–10 May

₹12,199 per night

Guest favourite

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!

11–18 Nov

₹13,469 per night

Guest favourite

Yurt in Randolph

4.96 out of 5 average rating, 386 reviews

4 Season Lower Yurt Stay on VT Homestead

We are located in the hills of central VT, close to good hiking, skiing and swimming. Our homestead is based in permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. No cleaning fee! This is one of three listings at our place. We can accommodate groups of six by booking: 4 season Lower Yurt Stay on VT Small Farm and Tiny house on VT homestead.

12–19 Nov

₹5,727 per night

Guest favourite

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.

26 Mar – 2 Apr

₹13,807 per night

Guest favourite

Flat in Rutland

4.96 out of 5 average rating, 522 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.

27 Oct – 3 Nov

₹8,271 per night

Guest favourite

Cabin in Warren

4.93 out of 5 average rating, 359 reviews

Cabin in the Woods

This cozy cabin is on a well maintained town (dirt) road a short walk to Blueberry Lake (on National Forest land, non-motorized) and is within 15 minutes of Breadloaf Wilderness Area, Sugarbush Ski Resort, Mad River Glen Ski Area, restaurants and dining, arts and crafts, sports and specialty shops. It's wooded, quiet, has a light open feeling inside.

21–28 Dec

₹10,138 per night

Holiday 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

28 Oct – 4 Nov

₹21,298 per night

Guest favourite

Chalet in Killington

4.9 out of 5 average rating, 159 reviews

Close to Mountain and walk to restaurants!

1–8 Jul

₹19,579 per night

Home in Killington

4.88 out of 5 average rating, 215 reviews

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

11–18 May

₹26,476 per night

Guest favourite

Loft in Monroe

4.94 out of 5 average rating, 194 reviews

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

15–22 Dec

₹11,622 per night

Apartment in Killington

4.77 out of 5 average rating, 282 reviews

Serene Killington Condo (resort style amenities)

13–20 Aug

₹14,159 per night

Guest favourite

Chalet in Killington

4.87 out of 5 average rating, 228 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

20–27 Nov

₹68,409 per night

Guest favourite

Apartment in Killington

4.97 out of 5 average rating, 116 reviews

#45 Mountain Ski & Summer Condo with Private Sauna

16–23 Aug

₹28,714 per night

Guest favourite

Loft in Ludlow

4.95 out of 5 average rating, 735 reviews

Spacious Renovated Barn Apt on 100 acres!

9–16 Oct

₹25,146 per night

Family- and pet-friendly home rentals

Guest favourite

Home in Goshen

4.82 out of 5 average rating, 250 reviews

Nature Lover's Paradise

21–28 Apr

₹11,818 per night

Guest favourite

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

The Barn at North Orchard, Near Middlebury

22 Feb – 1 Mar

₹10,402 per night

Guest favourite

Guest house in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

21–28 Jan

₹7,615 per night

Guest favourite

Guest house in Granville

4.9 out of 5 average rating, 785 reviews

Moon Valley Country Retreat no clean fee pets yes

20–27 Dec

₹9,382 per night

Guest favourite

Cottage in Brandon

4.91 out of 5 average rating, 266 reviews

Henrietta’s Hideaway-Walk Downtown!

6–13 Nov

₹8,449 per night

Guest favourite

Cabin in Woodstock

4.96 out of 5 average rating, 191 reviews

Cabin by the Stream on 27 Acres

1–8 Sep

₹18,211 per night

Home in Rochester

4.9 out of 5 average rating, 282 reviews

Mountain Home ready for you!

19–26 Sep

₹24,005 per night

Guest favourite

Guest house in Norwich

4.93 out of 5 average rating, 171 reviews

Vermont Log Guest Home-Close to Dartmouth

29 Sep – 6 Oct

₹15,682 per night

Family-friendly home rentals with a pool

Guest favourite

Apartment in Killington

4.92 out of 5 average rating, 392 reviews

April open 1 bedroom 1 night Ok Free shuttle

19–26 Sep

₹11,627 per night

Guest favourite

Guest suite in Killington

4.95 out of 5 average rating, 139 reviews

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

11–18 May

₹18,561 per night

Guest favourite

Apartment in Killington

4.82 out of 5 average rating, 250 reviews

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

11–18 Apr

₹18,727 per night

Guest favourite

Cabin in Bridport

4.92 out of 5 average rating, 133 reviews

Champlain Valley Alpacas

1–8 Mar

₹14,277 per night

Guest favourite

Flat in Barre

4.94 out of 5 average rating, 156 reviews

Relax in Recreation Paradise!

7–14 Sep

₹12,203 per night

Guest favourite

Guest suite in Ryegate

4.91 out of 5 average rating, 211 reviews

Secluded Paradise on the Connecticut River, VT

29 Jun – 6 Jul

₹15,800 per night

Guest favourite

Flat in Killington

4.92 out of 5 average rating, 119 reviews

Family and work friendly Spa at the Woods condo

30 Jul – 6 Aug

₹24,541 per night

Guest favourite

Apartment in Killington

4.86 out of 5 average rating, 107 reviews

Summer rental - Near Resort 4 Bedroom - Pool

22–29 Oct

₹28,891 per night

Quick stats about holiday 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
3.4T reviews
Nightly prices starting at
₹9,175 before taxes and fees

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