Family-friendly vacation rentals in Charles Town

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Charles Town

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 636 reviews

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Guest favorite

Guest suite in Nokesville

4.97 out of 5 average rating, 497 reviews

Horse farm near Manassas Battlefield.

Comfortable accommodations for horses and the people traveling with them. Private suite, private entrance (bedroom, bath, kitchenette) + 2 RV hookups water/electric. 6 stalls - nice paddock turnout. Lighted arena. Close to: Manassas Battlefield (25 mile trail); Skymeadow State Park (nice trails); several hunt clubs; VRE connections - to METRO; 3 miles to Manassas airport. Not accepting pets for the time being. Several wineries and breweries within 12 miles - ONLY 6 miles to Jiffy Lube Live.

Guest favorite

Place to stay in Bentonville

4.99 out of 5 average rating, 433 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. A large front porch with swing is waiting for you. @walnuthillcabin

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 237 reviews

City Charmer minutes from Old Town

Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

Guest favorite

Home in Charles Town

4.9 out of 5 average rating, 126 reviews

Historic Charles Town- Artist's Home

In historic downtown Charles Town, this relaxing home is a perfect get away and also close to many local attractions. Walk to restaurants, coffee shops, and boutiques. In a quiet neighborhood, 5 blocks from the charming downtown, this welcoming older house has historic details, charming artsy decor, covered front porch, covered back porch, and large fenced yard. One of the 4 bedrooms is on the 1st floor. 8 mins to historic Harpers Ferry, 12 mins to Shepherdstown shops and theater.

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 701 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Guest favorite

Tiny home in Purcellville

4.97 out of 5 average rating, 356 reviews

Tiny House near Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch. Guests enjoy private parking & plenty of privacy. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Guest favorite

Guesthouse in Purcellville

4.81 out of 5 average rating, 266 reviews

Barn Apartment in VA Wine Country

Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged - no satellite, TV, or Internet. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 469 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 acres. In addition, it is located only 2.5 miles from I-81 and approx 10 miles from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage has everything you need for a peaceful and enjoyable stay including full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more.

Guest favorite

Home in Harpers Ferry

4.94 out of 5 average rating, 383 reviews

Gayte House Gay Owned, Liberal Oasis

Cozy and charming 1840's home in the heart of town. Steps from the National Park, feet from the Appalachian Trail. Relax by the fire, on the porch or on the river. We have something for every season and every age. Steve and I have lived here In HF 20 yrs., 13 of those at the Gaytehouse. We live right next door now and Love both our homes. Please, Check out the beautiful and cherished home we offer for your stay.

Superhost

Home in Charles Town

4.85 out of 5 average rating, 266 reviews

Terra Alta - Incredible River Views and Hot Tub!

MOUNTAIN MAMA VACATION HOMES A huge hot tub, stunning hilltop views, the sound of rushing rapids below--this place has it all! On 3+ acres of private woodland set high on a hill overlooking the Shenandoah river, this large river house can accommodate many guests and is just 15-20 min from tons of attractions: whitewater rafting, historic Harpers Ferry, Virginia wine country, and more.

Guest favorite

Rental unit in Harpers Ferry

4.99 out of 5 average rating, 389 reviews

Taylor Den

John Brown’s stomping grounds! Adjoining the Harpers Ferry National Historical Park, just off the Appalachian Trail and a short jaunt from Old Town Harpers Ferry - TAYLOR DEN kindly welcomes and accommodates you. Delight in nature’s magic and the whimsy of Harpers Ferry with Taylor Den as your private home base.