
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.

⭐️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
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Robinson River Retreat - Near River, SNP & Graves
Great location near the Blue Ridge Mountains in Madison County for family or friends. 3 BR, 2 BA spacious house. Property continues across street to the peaceful Robinson River for swimming or fishing. Minutes to scenic trails at White Oak Canyon/Cedar Run and Old Rag in Shenandoah National Park. Many wineries and breweries are near by as well as seasonal festivals at Graves Mountain Lodge. Convenient to Culpeper and Charlottesville. Fiber Internet with 140 Mbps upload & download; 30 ms Latency
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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.
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Farm Cottage w. Blue Ridge views 15 mins from SNP
Carrie's Cottage is nestled in a private corner of our 150-acre Fairhill Farm. Delight in the bold views of the Blue Ridge Mountains. Hike our private trails. Fish in pond or river. Enjoy pool. Delight in farm animals including our miniature horses. Less than 20 mins from Shenandoah National Park and Appalachian Trail. Located 2 hours southwest of Washington, DC; 1 1/2 hours east of Richmond; and 25 minutes north of Charlottesville, VA. Near wineries; Monticello, Montpelier, Ash Lawn, and UVA.
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Spectacular Mountain Retreat
Cottage is the guest house of our country home. Situated on a mountain with spectacular views of the Blue Ridge and access to many hiking trails; biking; fishing and swimming in private pond only steps from the door. Cottage is located within easy driving distance of multiple wineries, Sky Line Drive and Shenandoah National Park; Montpelier; and restaurants and shops. We can accommodate no more than one dog, with prior permission. In April 2023, we again upgraded our internet (see below).
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Robinson River Roost - Cottage near Shenandoah NP
Enjoy a slice of country life in our rustic 2 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.
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Log Cabin and Ragged Rock Ridge
Mountaintop log cabin nestled in a mature, tranquil forest with spectacular views, ideally located near adventures like hiking in Shenandoah National Park (including Old Rag & White Oak Canyon), many local wineries/breweries/distilleries and quaint towns of Sperryville & Madison, VA. The authentic log cabin includes a cozy stone fireplace, porch, and patio with Old Rag views. Ponds, wildlife and hiking also available on the sprawling 300-acre property. Escape to the Cabin at Ragged Rock Ridge.
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One Of A Kind Home in VA Wine Country on 50 acres
Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.
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Spacious Shenandoah Home on 35 Private Acres
Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.
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Robinson River Cabin - Tri Creek Farm
If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.
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Red Gate Cabin: Hike into Shenandoah National Park
A true local gem, Red Gate Cabin is a one-of-a-kind, secluded, luxury cabin adjoining the Shenandoah National Park. You can hike directly from the cabin to the Appalachian Trail, Big Meadows, and Skyline Drive. At the cabin you will find modern amenities, including an EV charger, spacious outdoor decks, rocking chairs, smart TVs, a firepit, and much more! At 1,800 feet in elevation the air is cooler in the summer and views are spectacular year-round including the stars at night!
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Old Rag Mountain Stay w/WiFi, TV, Fire Pit, Patio
This unique, modern A Frame cabin is located at the foothills of The Shenandoah Mountains only minutes from Old Rag Mountain, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! This 400 sq ft. tiny home has all the modern amenities you need to feel right at home. Step outside, enjoy the mountain air, and relax on your private patio with a cozy,private fire. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!
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Popular amenities for Madison County family-friendly rentals
Family-friendly home rentals with a hot tub

Dreamy Couples Cabin With Hot Tub And Fire Pit
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New~Hot tub ~ firepit~ Cozy~ Wifi
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Log Cabin on 10 acres, 3 King bds, Hot Tub, Games
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Modern Cabin | Old Rag in Shenandoah National Park
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New, 5BD/4BA | hot tub, arcade, pool table, views
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Family Getaway at Cross Mountain
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Private Luxury Cabin w/ Shenandoah Mountain Views
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Fire Pit/MountainViews/Crib/Dog Friendly/Hot tub
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Family- and pet-friendly home rentals

Long Run Farm
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10-Acre Dog-Friendly House w Grill & Near Wineries
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Stay near Old Rag +White Oak Canyon—Cozy Log Cabin
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The Cabin at the Lake
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Private Fenced Yard for Dogs/Horses - 2BR Cottage
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Relaxing 2BR CABIN, 12 acres, dog friendly, hiking
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Unit B -Tatum’s Retreat -SAUNA- Hiking-Wineries
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Tranquility in the Mountains - Pet friendly!
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Family-friendly home rentals with a pool

Guest Cottage @ South River Farm
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Farm Studio with Blue Ridge views 15 mins from SNP
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The River House at the Swinging Bridge
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The Apartment at Dark Run Retreat
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Tiny Hideaway | StockTub+FirePit Shenandoah Trails
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Honeysuckle Farm - Secluded Luxury - 700 acres
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Mountain Cabin w/ Pool - Birdwatchers’ Paradise!
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Cornerstone Farms
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Destinations to explore
- Cabin rentals Madison County
- Rentals with lake access Madison County
- Rentals with a kayak Madison County
- Rentals with pools Madison County
- Farmstay rentals Madison County
- Bed and breakfasts Madison County
- Cottage rentals Madison County
- House rentals Madison County
- Pet-friendly rentals Madison County
- Rentals with a hot tub Madison County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Lake Anna State Park
- Jiffy Lube Live
- University of Virginia
- Early Mountain Winery
- Monticello
- James Madison University
- Glass House Winery
- Cardinal Point Winery
- Blenheim Vineyards
- Shenandoah River Outfitters
- Prince Michel Winery
- Sky Meadows State Park
- The Rotunda
- Downtown Mall
- Frontier Culture Museum
- White Oak Lavender Farm & The Purple WOLF Vineyard
- John Paul Jones Arena
- James Monroe's Highland
- Grand Caverns
- IX Art Park
- Massanutten Indoor WaterPark
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