Family-friendly vacation rentals in Madison County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Madison County

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

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Guest favourite

Cabin in Syria

4.95 out of 5 average rating, 221 reviews

⭐️Mongolian Yurt⭐️1100ft²⭐️Fire Pit⭐️Full Kitchen

Modern day interpretation of Mongolian yurt with view of Blue Ridge Mountains and the Rose River Valley • 17ft (5m) domed living room ceiling • Fire pit (wood supplied) • Fully equipped kitchen • Extremely safe neighborhood • Onsite, secured parking for 4 vehicles • 1,100ft² / 100m² • 50 inch Smart TV with satellite connection and movie channels . No cleaning fee or extra charges Note: High speed satellite WIFI is complimentary, though it can be impacted by weather. Follow us @roseriverfarm

Apr. 22 – 29

$474 CAD per night

Guest favourite

Bungalow in Stanardsville

4.93 out of 5 average rating, 241 reviews

Romantic, Carriage House Studio at Fairhill Farm

Delight in the bold views of the Blue Ridge Mountains while lounging on your private deck at the Carriage House on Fairhill Farm. Spring has sprung. We are open. Stroll on 300 acres Hike our private trails. Fish in private pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Located 2 hours southwest of Washington, DC, 1 1/2 hours east of Richmond and 25 minutes north of Charlottesville, VA. Near Shenandoah National Park, Monticello, Montpelier,Ash Lawn, and UVA

Mar. 25 – Apr. 1

$262 CAD per night

Guest favourite

Farm stay in Hood

4.99 out of 5 average rating, 231 reviews

Firnew Studio

Romantic getaway from the city. Private art studio on 265 ac. farm with spectacular Blue Ridge views, 15 min. to Shenandoah National Park. Deck overlooks pond. Perfect sunrise and sunset viewing. Walk to swimming hole, collect fresh eggs, feed goats, canoe in pond or simply relax on large private deck. Perfect for one couple. Close to wineries, breweries, hiking, Charlottesville, Montpelier, Monticello. 1.5 hrs from DC/ Richmond. Thanks to our many repeat guests for such kind reviews.

Dec. 28 – Jan. 4

$303 CAD per night

Guest favourite

Cottage in Syria

4.91 out of 5 average rating, 243 reviews

The Old Church Cottage~Old Rag,Kitchen,Grill, WiFi

Enjoy the Shenandoah Valley and Shenandoah National Park with us! Minutes from popular hiking trails, rivers and Graves Mountain Lodge, our Cottage is ideally situated to enjoy the local culture and festivals. If you're in the mood, DuCard Winery, Revalation Winery and Bald Top Brewery are nearby. When staying at The Old Church Cottage, you can relax in our hammock, grill in the back yard, fish in the nearby Rapidan or Rose Rivers or hike the Old Rag, White Oak and other close trails.

Apr. 17 – 24

$277 CAD per night

Guest favourite

Yurt in Etlan

4.95 out of 5 average rating, 193 reviews

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

Oct. 21 – 28

$200 CAD per night

Guest favourite

Home in Montpelier Station

4.93 out of 5 average rating, 462 reviews

The Cottage At Liberty Mill. Pets allowed $25

Brand new charming cabin with views of the Blue Ridge Mountains. Two bedrooms, Loft with 2 twin beds, two large bathrooms and a spacious common area. Exposed chestnut beams, working gas fireplace make this cabin a perfect getaway. All the amenities you could want. Located minutes from James Madisons' Montpelier, 5 minutes from Historic Orange, 30 minutes to Charlottesville, 20 minutes to Culpeper and less than 2 hours to Washington, DC. A loft area with 2 twin beds. Great for kids.

Oct. 28 – Nov. 4

$274 CAD per night

Guest favourite

Barn in Etlan

4.96 out of 5 average rating, 163 reviews

Hayloft Cottage

The Hayloft Cottage is open year-round for your country-living pleasure. Spring is coming! The flowers are starting up. This is your chance to get away from all the crowds and spend some peaceful down-time in your own, personal retreat. Enjoy the many local hiking trails, the fields, the mountains, and the fresh air. And feel free to bring the pups along (dogs only; limit 2). We have a fenced-in, 1.5 acre lot shared with our other cottage (Amy's Place) and ourselves.

Jun. 24 – Jul. 1

$223 CAD per night

Superhost

Cottage in Madison

4.92 out of 5 average rating, 148 reviews

Charming Guest Cottage at Winery

Early Mountain Vineyards' charming Guest Cottage, nestled next to our front block of grapevines and below our historic hilltop barn, offers breath-taking views of the Blue Ridge Mountains and a serene place to watch the sunset while sipping wine. Only short distance to our Tasting Room - open 5 days a week, Thursday - Monday. We recommend a reservation in advance - this can be made via our website, Early Mountain Vineyards, or by calling our winery directly.

Jul. 3 – 10

$460 CAD per night

Guest favourite

Guesthouse in Boston

4.98 out of 5 average rating, 148 reviews

The Bunkhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the bunkhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Sep. 2 – 9

$201 CAD per night

Guest favourite

Chalet in Brightwood

4.97 out of 5 average rating, 106 reviews

Charming Chalet in Blue Ridge Wine Country

NEW! PICKLEBALL/BASKETBALL COURT PUTT PUTT GOLF Sunset Ridge is in the heart of all you want to do! Newlyweds to families, everyone will love it here! The peace and quiet of the country, or the excitement of exploring new and different places, all await you! Check out our guidebook for local attractions, restaurants, nightlife, and sightseeing. Enjoy the serenity of the country! Follow us: @sunsetridgechalet

Nov. 22 – 29

$290 CAD per night

Guest favourite

Guesthouse in Madison

4.97 out of 5 average rating, 229 reviews

Hebron Valley Cottage

Nestled in the scenic Hebron Valley, this 2 bedroom 1 bath cottage is the perfect getaway from busy, city life. The cottage offers panoramic views of the Blue Ridge Mountains, including Old Rag and is located near several wineries, breweries, restaurants, antique shops, hiking trails and historic sites. The cottage is 3 miles from the town of Madison and is convenient to Charlottesville, Culpeper and Orange.

Nov. 29 – Dec. 6

$238 CAD per night

Superhost

Farm stay in Hood

4.98 out of 5 average rating, 232 reviews

The Thanksgiving House at Rapidan Valley Farm

Fall is on the way to Rapidan Valley Farm! It prime time for hiking on the farm or in the Shenandoah. This clean, cozy and inviting farmhouse is the perfect getaway. From wineries to historic sites to quaint southern main street towns, it's the best time of year to come and enjoy all that Central Virginia has to offer. Or, simply hideaway for the weekend and enjoy the beauty of the farm.

Oct. 18 – 25

$363 CAD per night