Family-friendly vacation rentals in Windsor County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Windsor County

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

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Guest favorite

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 17 – 24

€ 137 per night

Guest favorite

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.

Aug 2 – 9

€ 172 per night

Superhost

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

€ 171 per night

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 322 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Oct 16 – 23

€ 98 per night

Guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 433 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.

Nov 27 – Dec 4

€ 350 per night

Guest favorite

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.

Sep 20 – 27

€ 185 per night

Guest favorite

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

€ 120 per night

Guest favorite

Apartment in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

Dec 24 – 31

€ 135 per night

Guest favorite

Guesthouse in Norwich

4.93 out of 5 average rating, 171 reviews

Vermont Log Guest Home-Close to Dartmouth

Beautiful log guest home in Norwich, VT available for Dartmouth events or other local happenings features 1 bedroom (queen), loft (queen & futon), 1 bathroom-Can sleep 6+. Completely detached from main home. Located minutes from town in a private wooded property. Cozy up to the indoor fireplace or explore the local area. Many trails close by. Excellent location only 10 minutes to Dartmouth or 5 minutes to King Arthur Flour. Close to Quechee and Woodstock.

Aug 30 – Sep 6

€ 203 per night

Guest favorite

Guesthouse in Hartland

4.95 out of 5 average rating, 914 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter which offers 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for all Weekends. I require atleast a two night stay for the whole month of October. There is a "one" night stay fee of $40 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas grill available May - October

Apr 8 – 15

€ 150 per night

Guest favorite

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 17 – 24

€ 179 per night

Guest favorite

Guest suite in Mt Holly

4.98 out of 5 average rating, 117 reviews

Exquisite Green Mountain Loft Haven

Lovely apartment in country home affords privacy plus all the necessities of home. Beautiful grounds and views afford relaxation and invigoration. Ski at local ski resorts or snowshoe or sled right outside your door. Comfortable beds, peace and quiet, and dark skies means great sleeping. Fully stocked kitchen, and nearby summer activities makes staying here fun and enjoyable. Come find out what others already know!!

Nov 13 – 20

€ 146 per night