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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Guest favorite

Tiny home in Reva

4.98 out of 5 average rating, 127 reviews

The Tool Shed, Pet Friendly

The Tool Shed at Mountain Field farm is the perfect place to relax and leave the city behind! We are located just 20 minutes from Old Rag Mountain, White Oak Falls and several wineries and breweries as well as the quaint town of Culpeper. Spend time with the horses they love peppermints. Nearby Culpeper is charming with an array of restaurant . The Tool Shed is pet and family friendly with spacious areas to explore We are 100% Dog Friendly Off leash allowed. Doordash is available as well.

Guest favorite

Rental unit in Madison

4.9 out of 5 average rating, 249 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Guest favorite

Farm stay in Madison

5 out of 5 average rating, 225 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.

Guest favorite

Cottage in Madison

4.91 out of 5 average rating, 163 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 3 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.

Guest favorite

Guesthouse in Syria

4.96 out of 5 average rating, 363 reviews

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Guest favorite

Cabin in Etlan

4.99 out of 5 average rating, 118 reviews

Cozy Mountain Cabin w/WiFi, TV, Fire Pit,Patio

This cozy getaway is located only minutes from Old Rag, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! Our A-frame cabin is a 400 sq ft space with all the modern amenities, a private patio with a stone fire pit, loft bedroom, and spacious bathroom. Unwind, relax, and enjoy some time at the beautiful mountains….a couples getaway, friends retreat, or vacay with the kiddos! Are your desired dates already booked? Check out our other listing, Bald Eagle Cabin

Guest favorite

Cottage in Orange

4.95 out of 5 average rating, 413 reviews

Private Fenced Yard for Dogs/Horses - 2BR Cottage

2BR Hen and Hound Cottage is located just outside Orange, VA and has a private fenced yard for pets and walk-in access to adjacent James Madison's Montpelier and its many walking trails. In addition, we are minutes away from all of the popular wedding venues in Orange and a short drive to Shenandoah National Park. Our house on Whistle Stop Farm (so named for the train that passes by) is next to the cottage if you need us. Otherwise, the place is yours. Come enjoy some time in country!

Guest favorite

Home in Robertson

4.92 out of 5 average rating, 204 reviews

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.

Guest favorite

Yurt in Etlan

4.95 out of 5 average rating, 213 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

Farm stay in Brightwood

4.96 out of 5 average rating, 122 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

Guesthouse in Boston

4.98 out of 5 average rating, 174 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.

Guest favorite

Cottage in Madison

4.99 out of 5 average rating, 146 reviews

Fishback Cottage, Central location

Centrally located in the country side of Madison, VA. With easy access to route 29 and closely located to local breweries, wineries and hiking. Speedy wifi makes it easy for a business trip or for a night of relaxation with Netflix. 7 Min Drive to Renback Barn or Early Mountain Vineyards 17 Mile Drive to White Oak Canyon or Old Rag trails 25-30 Min Drive to Charlottesville or Culpeper