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, 261 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

A charming two-story cottage is depicted, featuring a white exterior with black shutters. A spacious porch welcomes visitors with steps leading to the entrance, surrounded by a well-maintained green lawn and a few small plants. Large windows allow for natural light.

Home in Hood

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.

Superhost

The cottage is surrounded by trees, featuring a hammock strung between two branches. A kitchen area with wooden cabinetry and ample counter space is visible. The living space includes a comfortable sofa and a rustic coffee table, while large windows allow natural light to brighten the room.

Farm stay in Sperryville

4.87 out of 5 average rating, 193 reviews

The Cottage @ Sharp Rock Vineyards at Old Rag Mtn.

The Cottage is the original farmhouse built in 1794 when the farm was founded .We are located on the Hughes river ( native trout fishing) at the foot of Old Rag Mountain only two minutes from the parking lot @ Old Rag. Access to White Oak Canyon and Shenandoah National Park are only minutes away. We are also a working vineyard and winery with our tasting room open Friday thru Sundays and by appointment. We also have our riverside CARRIAGE HOUSE perfect for a couple. See our separate listing.

Guest favorite

A charming cabin with light-colored wood siding is set against a snowy landscape. A welcoming wreath adorns the front door. The surrounding area features tall trees blanketed in white snow, with steps leading up to the porch where a rocking chair is placed.

Home in Montpelier Station

4.93 out of 5 average rating, 507 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. Beautiful.

Guest favorite

The guesthouse exterior features a rustic wooden façade with a shingled roof. A spacious deck enhances the entryway, adorned with potted plants and grass arrangements. An umbrella stands in a seating area, providing shade for outdoor relaxation, amid a backdrop of trees.

Guesthouse in Ruckersville

4.98 out of 5 average rating, 280 reviews

Mountain Guesthouse*Hot Tub*WiFi*Firepit*Grill*SNP

Stay in a modern 1-bedroom guesthouse with hot tub access, queen bed, deck, grill, firepit, electric fireplace, TV/WiFi and pastoral mountain views. Situated on a 42 acre forest preserve with hiking/walking paths to expore yet close to services (3 miles), historic areas (Montpelier, Gordonsville), wineries/breweries (Stone Mountain, Montifalco, Patch, Bald Top), hiking (SNP, Preddy Creek), and venues (Lydia, Barn at Edgewood) and 15-30 miles from Charlottesville, Massanutten, and Harrisonburg.

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.

Home in Luray

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 :)

Top 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, 225 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.

Top guest favorite

The exterior of a historic farmhouse is shown, featuring a light yellow facade and a green metal roof. Brick pathways lead to a covered porch with seating. Lush greenery surrounds the property, with flowering plants in the foreground and a stone chimney accentuating the structure.

Home in Madison

4.98 out of 5 average rating, 222 reviews

Enchanted-Historic Shenandoah Farm

A distinctive historic farm and modern home available for an exclusive rental experience. The house was completely restored in 2005 adding a new addition that houses a large modern kitchen, and 3 full baths (over 3,800 sq ft). A top Washington decorator designed the home specifically to create an ideal family/friends active getaway, explore its 110 private acres full of old fashioned activities. Please note that this property is not set up to accommodate weddings or events.

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

Superhost

The cottage's welcoming exterior features a covered front porch with white railings, flanked by lush greenery and flower beds. A set of stone steps leads to the front door, which is centered between two large windows under a metal roof.

Cottage in Madison

4.92 out of 5 average rating, 158 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.

Guest favorite

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, 183 reviews

Walnut Run Farm - Private & Quiet - Sperryville

A beautiful old farm in the foothills of the Blue Ridge Mountains. The 1880 farmhouse sits on a small stream that runs through the entire fifty-five acre property. The house is clean, minimally decorated, with pasture views out of every window. The farm is located 80 miles from Washington DC and just down the road from Sperryville, Shenandoah National Park, Old Rag Mountain, Luray Caverns, The Inn at Little Washington and other local attractions.

Guest favorite

The exterior of a red cottage is framed by blossoming yellow forsythia and clusters of vibrant daffodils. Tall grass sways gently in the breeze, complemented by a tree that provides shade. Large windows offer a glimpse of the cozy interior, bathed in natural light.

Barn in Etlan

4.97 out of 5 average rating, 173 reviews

Hayloft Cottage

The Hayloft Cottage is open year-round for your country-living pleasure. Spring is here! 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.