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Kid-friendly vacation rentals in Madison County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Madison County

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

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Top guest favorite

A scenic view of a pond surrounded by open land and trees reveals a family enjoying the outdoors. Mountains are visible in the background, creating a peaceful and spacious setting. The landscape includes a small structure near the pond, contributing to the rural charm.

4.98 out of 5 average rating, 289 reviews

Firnew Cottage

A perfect family getaway from the city in the heart of Virginia Wine Country, 15 min from Shenandoah National Park, 30 min from Charlottesville. Private cottage on 265 acres with 3 mi. hiking trail, overlooks 2 ponds/playhouse offers complete farm experience. Walk to swimming hole on river, canoe/fish in lake, feed peacocks/ goats, collect fresh eggs. Great sunsets. Fire-pit. Close to wineries, breweries, Montpelier, Monticello - only 1.5 hrs to DC/Richmond. Pet friendly. Tour included.

Top guest favorite

A wooden porch is featured overlooking a sprawling green valley. Rolling hills, trees, and distant mountains are visible against a softly lit sky during sunset, enhancing the serene surroundings.

Cabin in Stanley

4.99 out of 5 average rating, 184 reviews

New~5BD/4BA~Upscale~Arcade~LL

★New LUXE cabin, new build, A+ views, 2880 sf ★5 king bedrooms, 4 full baths (2 en suite, 1 adjoining, 1 hall) ★In Shenandoah Woods ★Arcade & board games, books, 6 ft pool table ★Porches & hot tub overlooking valley & mountains ★Fire pit ★Electric outdoor grill ★Fireplace (elect.) ★Smart TVs (incl. a 70") ★Fast WiFi ★Dining for up to 10 people (with extension) ★Firewood provided for fire pit ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray/Luray Caverns ★25 mins-Shenandoah National Park

A charming cottage is set against a backdrop of lush trees. A welcoming front porch with white railings encircles the entrance. The property features landscaped areas with low shrubs and concrete steps leading to the front door.

Home in Stanardsville

4.91 out of 5 average rating, 198 reviews

The Conway House

Get away on the Conway, a place to recharge, relax and explore. Located just outside a back entrance to the Shenandoah national park. Walk, run, or bike these lightly traveled country roads to access the trail heads. This private cottage is the ideal location for visiting the Shenandoah national park, hiking, fishing, biking, wineries, and getting away to relax. This newly remodeled mountain retreat is updated with modern decor and all the essentials for an unforgettable mountain getaway.

An open concept living area features a comfortable sofa, a wall clock, and a wooden ladder leading to a loft. Natural light fills the space, showcasing modern appliances and a cozy dining nook. Exposed beams highlight the rustic charm of the newly renovated interior.

Cottage in Orange

4.9 out of 5 average rating, 173 reviews

Willie's Place Country Cottage Pets Allowed

Step out your front door and pet horses located next door. Willie's place is newly renovated and has all the amenities you need. Located close to wineries, shopping, wedding venues, Historic Montpelier, Corn Maze, Town of Orange, Woodberry Forest School, 10 minutes to Gordonsville, 30 minutes to Charlottesville. Kayak the Rapidan, take a horseback ride at Oakland Heights or see a play at Barboursville. Exposed beams throughout, a beautiful Loft and back porch for sitting. You won't go wrong.

Top guest favorite

The living room features two green lounge chairs facing a wooden coffee table, surrounded by a brown couch and a vibrant blue area rug. The front door, framed by windows, adds natural light, while a bookshelf filled with books creates an inviting reading corner.

4.99 out of 5 average rating, 595 reviews

Modern Farmhouse near Shenandoah Nat'l Park + Lake

Enjoy our secluded 1850s solid brick farmhouse. Completely renovated with modern conveniences, including central AC & Starlink internet. Five miles from the Shenandoah National Park and Luray Caverns. Short walk to Lake Arrowhead. We also own the downtown cafe, Broad Porch Coffee, so are local and can help if you ever need anything. We are family friendly and love dogs (no pet fee). Our goal is to provide a clean, safe, comfortable stay! Please read our reviews for an unbiased opinion :)

A wide-open green field is framed by tall trees, with gentle hills in the background. The landscape is bathed in soft morning light, revealing a serene and expansive outdoor space. Fencing outlines the area, enhancing the natural beauty.

Tiny home in Reva

4.96 out of 5 average rating, 137 reviews

The Tool Shed, Pet Friendly

The Tool Shed at Mountain Field Farm provides a delightful retreat just a short 20-minute drive from the majestic Old Rag Mountain and the serene White Oak Falls. Immerse yourself in the breathtaking landscape, explore the nearby exquisite wineries and craft breweries, and meander through the quaint streets of Culpeper, where adventure blends seamlessly with relaxation and fine dining. Don’t forget to bring along some peppermints for our gentle horses, who are always eager to greet visitors.

An inviting game room is presented, featuring a foosball table at the center. A cozy sofa with bright cushions is positioned near large windows that overlook the greenery outside. A warm area rug adds a comfortable touch, while natural light fills the space.

Cottage in Luray

4.84 out of 5 average rating, 102 reviews

Creekside Cottage at Shenandoah

Welcome to our secluded cottage in the woods overlooking Shenandoah National Park! Your home base is located 10 mins from the cute town of Luray, through idyllic farmland and on acres of private hillside forest along a relaxing creek. As you enter this 3br/2ba home, you’ll find cozy cottage charm with thoughtful updates and modern amenities complete with a private hot tub. Within ~20 mins you'll find: - Shenandoah NP entrance - Luray Caverns - Wine country - Canoeing the Shenandoah River

4.79 out of 5 average rating, 108 reviews

Serendipity with a View. (cozy mountain retreat)

If you want relax with a quiet mountain view. WE HAVE STARLINK WIFI. Very little to no cell sevice. Serendipity is perfect place to reconnect with a family, group of friends, or romantic getaway ( Fire place inside, games, books) Fabulous view is Graves Mountain. Great hiking with the famous Whiteoak Canyon Trail and Old Rag Mountain Trail, just to name a few. Lots of local wineries to explore. Robinson River steps away for great trout fishing. Private pond access .25 away.

A cabin is illuminated warmly against a starry night sky, surrounded by tall trees with sparse foliage. The screened-in porch features large windows, reflecting the evening light. The landscape creates a serene and secluded atmosphere, inviting guests to connect with nature.

4.97 out of 5 average rating, 230 reviews

Modern Cabin | Old Rag in Shenandoah National Park

Stay near the best mountain trails in Shenandoah National Park with a few wineries and breweries close by. You'll have access to ... -- Our private creek and swimming hole -- A hot tub under the stars -- Starlink WiFi with up to 200 Mbps download speeds, adequate for remote work and streaming services (see more below) -- A kitchen fully stocked with all the equipment you'll need to prepare your own meals -- 2 bedrooms and an inflatable mattress in the common area

Top guest favorite

The entrance to Fairhill Farm is marked by a white wooden sign displaying the name, set against a backdrop of rolling hills adorned with autumn foliage. A vibrant red bush frames the sign, contributing to the natural beauty of the landscape.

Home in Stanardsville

4.98 out of 5 average rating, 146 reviews

Charming Carrie's Cottage at Fairhill Farm

Carrie's Cottage is nestled in a private corner of our Fairhill Farm. Delight in the bold views of the Blue Ridge Mountains. Hike private trails on our 150 acres. Fish in 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 wineries; Shenandoah National Park and AP; Monticello, Montpelier, Ash Lawn, and UVA

A cozy screened porch is adorned with string lights, enhancing the inviting ambiance. A yellow sofa is surrounded by colorful cushions, while a wooden table sits in the center. Large windows allow natural light to illuminate the space, which features natural wood walls.

Cabin in Pratts

4.96 out of 5 average rating, 140 reviews

Stunning Modern Cabin w WiFi near Shenandoah Park

My family lovingly restored this log cabin and it was recently featured in the Washingtonian as one of the top places to visit in the DC region! We’re so excited to share it with you! It is one of the only houses in the area with reliable high speed xfinity wifi. It is a short drive to so many of the popular Shenandoah National Park hikes and it's centrally located to so many of the popular breweries, wineries, restaurants, and adorable small towns.

A multi-purpose sports court is shown, featuring a red playing surface with white lines for both pickleball and basketball. Surrounding greenery adds a natural backdrop, while two light posts provide illumination for evening activities.

Chalet in Brightwood

4.96 out of 5 average rating, 142 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

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Madison County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

A well-lit basement area features blue walls adorned with decorative elements. A wooden dresser is placed against one wall, while two director's chairs sit beside a small circular table. A globe is mounted on the wall, adding to the inviting space for socializing or games.

Home in Madison

5 out of 5 average rating, 8 reviews

Family Friendly Cottage Game Room, Fire Pit & More

A spacious living area features a light gray sectional sofa with decorative pillows, a coffee table, and hardwood flooring. Large windows allow natural light to fill the room. A ceiling fan hangs from a high ceiling, and a television is mounted on the wall.

4.96 out of 5 average rating, 141 reviews

Peacefield - Blue Ridge views near Culpeper

The exterior of the home features a traditional two-story structure with white siding and blue shutters. A welcoming front porch is adorned with potted plants and a seasonal wreath. Lush greenery surrounds the entrance, leading to a stone pathway.

4.97 out of 5 average rating, 119 reviews

Monrovia on Main

Top guest favorite

A game room is displayed featuring a foosball table and a pool table, accompanied by a red seating area and recliners. The walls are adorned with framed artwork, and a ceiling fan is positioned overhead, contributing to a comfortable recreational space.

Home in Stanardsville

4.96 out of 5 average rating, 26 reviews

The Madelyn

A landscaped outdoor area features a circular arrangement of white chairs surrounding a firepit, set amongst greenery. Paths of stone lead through the yard, with lush trees and shrubs providing natural shade and a peaceful ambiance.

Home in Madison

4.96 out of 5 average rating, 406 reviews

Unit A-Mountain Retreat- SAUNA-Hiking-Wineries

An open living area displays a cozy seating arrangement with a gray sofa and a wooden coffee table. A modern kitchen is visible in the background, featuring stainless steel appliances and natural light flowing through large windows. A wooden staircase leads to the upper level.

Home in Madison

4.94 out of 5 average rating, 116 reviews

Designer cabin in the woods at Shennadoah NP

Top guest favorite

A spacious family getaway is set amongst lush greenery, with dandelions in the foreground. The home features a combination of wooden siding and large windows, surrounded by trees showcasing their seasonal foliage under a clear blue sky.

4.99 out of 5 average rating, 135 reviews

Spacious Retreat with Outdoor Firepit & Large Deck

An exterior view of a white farmhouse with a green metal roof is showcased, featuring a screened porch with white railings. Adjacent to the house, a traditional barn structure is visible, surrounded by a grassy area and trees, reflecting the serene countryside landscape.

Home in Woodville

4.86 out of 5 average rating, 184 reviews

Walnut Run Farm - Private & Quiet - Sperryville

Kid-friendly apartment rentals

A modern kitchen features a large stainless steel island with a smooth surface, complemented by wooden cabinetry. In the background, a spacious living area is visible, furnished with a couch and decorative accents, creating an inviting open-concept layout.

Apartment in Charlottesville

4.92 out of 5 average rating, 589 reviews

Luxury, open space, in the HEART of Belmont!

Top guest favorite

Apartment in Madison

4.96 out of 5 average rating, 218 reviews

The Apartment at Dark Run Retreat

An open-plan living space is featured, showcasing comfortable seating arrangements, including a beige sofa and dark chairs. A coffee table is positioned centrally, with a TV unit nearby. Light walls and warm lighting create an inviting atmosphere, complemented by a patterned area rug.

Apartment in Charlottesville

4.84 out of 5 average rating, 578 reviews

★1 BR Private Apartment in Downtown Cville★

Apartment in Charlottesville

4.91 out of 5 average rating, 118 reviews

Lovely apartment in Belmont Cville neighborhood

Top guest favorite

A living room area features a soft gray sofa paired with a brown leather armchair. A circular coffee table rests on a vibrant red area rug. The space is illuminated by natural light, highlighting the attached kitchen in the background.

Apartment in Charlottesville

4.91 out of 5 average rating, 235 reviews

Charming St. Charles

A living area features a light-colored sofa adorned with an accent pillow, positioned next to a textured area rug. A coffee table with a geometric base stands in the center, surrounded by artwork on the walls. A ceiling fan and window provide the space with natural light.

Apartment in Charlottesville

4.92 out of 5 average rating, 454 reviews

Private appartment in Charlottesville / Belmont

A comfortable living area features a dark sofa with decorative cushions, a light-colored coffee table, and a TV stand with storage. Wall art depicting trees adorns the turquoise walls, and a ceiling fan provides air circulation, adding to the room's inviting feel.

Apartment in Woodstock

4.87 out of 5 average rating, 569 reviews

Heart of Town-Pet Friendly

Top guest favorite

The exterior view of the house features a light yellow façade with white trim and a front porch supported by two columns. A pathway leads to the wooden front door, surrounded by landscaped greenery and blooming flowers. Tall trees provide a natural backdrop.

Apartment in Charlottesville

4.99 out of 5 average rating, 281 reviews

Fabulous Terrace Level Apartment In City

Kid-friendly condo rentals

A scenic view of a waterfront area is captured, featuring a wooden dock with boat slips and a smooth path lined with rocks. Trees adorned in autumn colors frame the calm water, enhancing the peaceful atmosphere of the lakeside setting.

Condo in Mineral

4.94 out of 5 average rating, 47 reviews

Beautiful waterfront condo w/private boat slip

A series of ski gondolas are seen ascending a mountain, suspended from overhead cables. Snow-covered slopes can be observed below, with a bright blue sky providing a clear backdrop. The gondolas feature large windows, allowing views of the winter landscape.

Condo in McGaheysville

4.84 out of 5 average rating, 144 reviews

Massanutten Woodstone 2-BR, 2 Bath

A sunlit sunroom features large panoramic windows offering views of the outdoors. Comfortable seating is arranged with two wicker sofas and a daybed, accented by vibrant cushions and a decorative blanket. A coffee table sits in the center on a striped area rug.

Condo in Charlottesville

4.91 out of 5 average rating, 173 reviews

Luxurious Posh Downtown Condo

A bright bedroom features a spacious bed flanked by two bedside tables with lamps. A framed cityscape artwork adorns the wall above the bed. Dark curtains frame the window, and a patterned rug covers the hardwood floor, creating a cozy yet modern ambiance.

Condo in Charlottesville

4.91 out of 5 average rating, 102 reviews

The Townie 3 BD/2BA Historic Downtown Building

A spacious living area is highlighted by a large sectional sofa and a round coffee table. A dining table set for six is positioned nearby, with contemporary light fixtures overhead. The kitchen area features dark cabinets and appliances, while natural light filters through the windows.

Condo in Massanutten

5 out of 5 average rating, 4 reviews

In Massanutten Resort! Sleeps 6. Full Kitchen!

A cozy bedroom features a large bed adorned with a blanket and decorative pillows. A warm wooden accent wall complements the natural light streaming in through large windows. A small table and a plant add to the inviting atmosphere, while a floor lamp provides additional illumination.

Condo in Charlottesville

4.95 out of 5 average rating, 44 reviews

Lovely 2 bed 2 bathroom condo close to UVA

A spacious living area features a comfortable arrangement of seating, including a plush sofa and an armchair beside a simple wooden table. A brick fireplace acts as a focal point on one wall, while sliding glass doors provide access to an outdoor balcony.

Condo in Charlottesville

4.86 out of 5 average rating, 130 reviews

Perfect Spot in Charlottesville

Top guest favorite

A well-appointed bedroom features a spacious bed with decorative bedding and two bedside lamps. Natural light filters through a window adorned with drapes. A wooden desk and chair are positioned nearby, providing a functional workspace.

Condo in Massanutten

5 out of 5 average rating, 5 reviews

7 Day Vacation in Massanutten Resort, VA

Destinations to explore