Family-friendly vacation rentals in Madison County

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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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Top guest favorite

A modern yurt is showcased with a domed roof and wooden exterior, surrounded by a green lawn. The large windows offer views of the landscape, while a spacious porch extends around the front. Autumn foliage adds color to the background.

Cabin in Syria

4.96 out of 5 average rating, 276 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

Top guest favorite

An A-frame cabin is set against a backdrop of vibrant autumn foliage. The cabin features a textured dark exterior and a welcoming orange front door. Neatly lined stone steps lead to the entrance, surrounded by landscaped gardens and seasonal decorations.

Cabin in Etlan

4.99 out of 5 average rating, 154 reviews

Modern Mountain Getaway w/WiFi, TV, Fire Pit,Patio

Come escape to our cozy retreat amidst the stunning beauty of the Shenandoah National Park region. Our unique 400 sq ft tiny home offers all the modern amenities, fully equipped kitchen, private patio w/ fire pit, loft bedroom , and spacious bathroom. Only minutes from Old Rag Mountain, wineries, breweries, horseback riding, trout fishing, and more. Unwind & relax after a day of exploring on your spacious patio.Are your desired dates already booked? Check out our other listing, Bald Eagle Cabin.

Top guest favorite

The great room features exposed wooden beams and a stone fireplace, providing an inviting space. A comfortable sectional sofa faces the fireplace, accompanied by two blue armchairs and a wooden coffee table. Large windows allow natural light to fill the room, showcasing the surrounding scenery.

Farm stay in Madison

5 out of 5 average rating, 246 reviews

Rustic Farmhouse on Farm W/ Mountain & River Views

The retreat at Rooted Land Co. consists of 1 farmhouse and 3 luxury tiny cottages on 350 private acres nestled at the base of the Blue Ridge Mountains with more than 1-mile of Rapidan River frontage. Each home is spaced with privacy in mind and positioned with breathtaking views. Countless outdoor activities including fishing, hiking, and wildlife viewing provide a unique experience during your stay. Rooted Land Co. is located just minutes from wineries, breweries, and Shenandoah National Park.

Top guest favorite

The log cabin exterior is highlighted by a stone chimney and a welcoming porch with steps leading to the entrance. Lush green trees surround the cabin, creating a serene atmosphere in the tranquil forest setting.

Cabin in Madison

5 out of 5 average rating, 153 reviews

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.

Top guest favorite

The log cabin exterior is showcased, featuring a welcoming front porch with wooden railings. Stairs lead up to the entrance, flanked by natural stone landscaping. Surrounding trees create a serene atmosphere, while warm lighting from the windows adds a cozy touch.

Guest suite in Reva

4.96 out of 5 average rating, 124 reviews

The Log Cabin at Ridgeview - Hiking, Wine, UVA

Entire main floor of quaint log cabin in the heart of Virginia's Wine Country. Close to Charlottesville airport, UVa campus, Shenandoah National Park, wineries, breweries, local restaurants. NOTE: Prices shown are for 2 bedrooms, 1 queen and 1 double, and 2 baths. For access to 3rd bedroom, at an additional fee which includes one double and one single, set number of guests to 5 or 6. Access to laundry. Cozy front porch, tons of parking, screened in porch out back for dining or relaxing.

Guest favorite

The exterior of the country house showcases a rustic red façade complemented by a covered front porch. A welcoming entryway is flanked by lush greenery and a gravel driveway, evoking a serene rural atmosphere amid the surrounding trees.

Cabin in Reva

4.94 out of 5 average rating, 158 reviews

10-Acre Dog-Friendly House w Grill & Near Wineries

Welcome to the Reva Retreat! This country house sits on 10 acres, nestled between Shenandoah Nat'l Park & the Blue Ridge Mtns, with wineries and breweries nearby. Approx 1.5 hours from DC and 45 mins from Charlottesville makes this the perfect getaway destination to escape the city & unplug. Stocked with amenities: BBQ grill, dine al fresco, stargaze by the firepit, cook a feast in the new kitchen, play board games in the basement, or connect your laptop to a 32" monitor to work remotely.

Guest favorite

The yurt is set against a starry night sky, surrounded by towering trees. A spacious deck leads to the yurt's entry, while warm light emanates from its windows. The scene showcases a natural ambiance highlighted by foliage and a gravel path leading to the entrance.

Yurt in Etlan

4.96 out of 5 average rating, 235 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.

Guest favorite

The spacious deck extends along the length of the house, featuring several white rocking chairs positioned for scenic views of the surrounding landscape. Cloudy skies create a serene atmosphere, highlighting the natural beauty of the nearby hills and fields.

Home in Madison

4.96 out of 5 average rating, 163 reviews

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.

Superhost

An open-plan kitchen and living area is showcased with wooden beams and large windows, allowing natural light to illuminate the space. A kitchenette features wooden cabinetry, a microwave, and a small dining bar with three tall stools. A rocking chair is positioned beside a window overlooking the woodland.

Farm stay in Brightwood

4.93 out of 5 average rating, 141 reviews

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.

Guest favorite

An aerial view of the historic Woodbourne Estate Manor showcases its striking red roof and white facade. The surrounding landscape features lush greenery, expansive fields, and well-maintained gardens. Pathways are visible leading to the entrance, enhancing the inviting atmosphere of this picturesque estate.

Farm stay in Madison

4.96 out of 5 average rating, 111 reviews

Brewery Manor Sleeps 10 Heated Pool Hot Tub

Woodbourne Estate, circa 1810, is a National and Virginia historic registered landmark Manor House and farm nestled in the foothills of the Blue Ridge Mountains in Madison, Virginia. The 53-acre Estate is also home to our award-winning Bald Top Brewing Company which sits just a comfortable stroll beyond the Manor house. This magical Manor, with its gorgeous grounds, gardens, barns, ruins, pool, stream and vistas awaits! The Manor at Bald Top: Drink in the Moment!

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, 152 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

Top guest favorite

A covered porch area is visible, featuring several outdoor chairs and a table. The porch is bordered by a gravel path and landscaped with stones and flowers. The expansive grassy field extends beyond the structure under a clear blue sky.

Guesthouse in Madison

4.97 out of 5 average rating, 250 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.