Family-friendly vacation rentals in Berkeley County

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Top-rated family-friendly rentals in Berkeley County

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

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Guest favorite

Guest suite in Shepherdstown

4.95 out of 5 average rating, 568 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.

Sep 22 – 29

G$17,615 GYD per night

Guest favorite

Cabin in Berkeley Springs

4.83 out of 5 average rating, 180 reviews

Retriever’s Retreat ~ High-Tech Log Cabin Oasis

Relax at the gorgeous 3BR 2Bath log cabin nestled in the mesmerizing forest setting of Berkeley Springs, WV. Recently renovated to bring in more outdoor light and modernize the cabin, its fantastic location just a few minutes from the booming Cacapon Resort State Park offers a perfect escape from the everyday hustle and bustle Stylish design and a rich list of high-tech amenities ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Basement Entertainment ✔ Sunny Deck ✔ Backyard ✔ High-Speed Wi-Fi

Dec 6 – 13

G$34,972 GYD per night

Guest favorite

Guest suite in Sharpsburg

4.99 out of 5 average rating, 167 reviews

The River Bend Retreat ~ C&O Canal ~ Antietam

Welcome to The River Bend Retreat at Taylor's Landing: a relaxing get-away along the C&O Canal Towpath and the Potomac River. Whether you're in the area to enjoy the river and the towpath, soak up some history at Antietam National Battlefield, or explore the quaint nearby towns and attractions, we look forward to hosting your stay! The RBR's 2 bedrooms and 1 bathroom can accommodate up to 4 guests. Visit us online for even more details, information, and local recommendations. See you soon!

Aug 1 – 8

G$27,762 GYD per night

Guest favorite

Guesthouse in Middletown

4.95 out of 5 average rating, 246 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

Jul 9 – 16

G$22,153 GYD per night

Guest favorite

Cabin in Lovettsville

4.97 out of 5 average rating, 120 reviews

Rustic cabin + modern luxury in Lovettsville

Enjoy a one-of-a-kind stay in this restored 1800s cabin guest house with modern updates and beautiful decor. Off the beaten track but only about 1 hour from both DC and Baltimore. Located on a working farmstead and close to wine country, breweries, a goat cheese creamery, farm-to-table dining, and more. A favorite landing place for those out in the country enjoying Loudoun's Artists' Tour, Farm Tour, Wine Country Half Marathon, a wedding, a hiking trip, or just a weekend in the countryside.

Oct 9 – 16

G$28,725 GYD per night

Guest favorite

Home in Winchester

4.97 out of 5 average rating, 214 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.

Feb 2 – 9

G$22,105 GYD per night

Guest favorite

Cottage in Winchester

4.97 out of 5 average rating, 425 reviews

Emma's Stone Cottage

Relax and unwind in the privacy of this wonderful stone cottage, which sits on 15 beautiful acres. In addition, it is located only 2.5 miles from I-81 and 14 minutes from Winchester Medical Center, Old Town Winchester, Shenandoah University and much more. Our cottage is fully furnished with all the comforts of home. From the full kitchen, central air, water softener, HD smart televisions, Wifi, outdoor firepit and more. It has everything you need for a peaceful and enjoyable stay.

Nov 18 – 25

G$25,649 GYD per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 644 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.

Apr 22 – 29

G$19,158 GYD per night

Guest favorite

Cabin in Berkeley Springs

4.93 out of 5 average rating, 469 reviews

Horizon Hill-Log Cabin w/Hot Tub & Views!

Horizon Hill is a beautiful log home in Berkeley Springs, WV. Less than 2 hours from DC & Baltimore. Great for couples, families, and groups. Large three level deck with hot tub to enjoy the amazing mountain views. Warm up to next to the fire place at night. Nicely decorated and equipped with super fast Starlink Wi-Fi, Netflix, Amazon Prime & fully stocked kitchen for cooking. Only 2 minutes to Cacapon State Park and 15 minutes (easy drive) to Berkeley Springs. Dogs welcome!

Jul 28 – Aug 4

G$50,911 GYD per night

Guest favorite

Farm stay in Knoxville

4.97 out of 5 average rating, 262 reviews

Paradise Farm—Near Harpers Ferry

If you love animals and the country this is the place for you! Come visit our "paradise." Horses, cows, goats, donkey and a range of feathered exotics are right out your front door. Short drive to the Potomac river, C&O Canal, Harpers Ferry National Historic Park, Antietam Battlefield, Appalachian Trail, Shepherdstown, WV. Outfitters nearby offer rafting, kayaking/canoeing, tubing, ziplines. Vineyards all around. Hosts live in attached house and are nearby if needed.

Aug 5 – 12

G$25,985 GYD per night

Guest favorite

Tiny home in Purcellville

4.96 out of 5 average rating, 314 reviews

Remote Tiny House in 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!

Mar 5 – 12

G$29,940 GYD per night

Guest favorite

Apartment in Harpers Ferry

4.99 out of 5 average rating, 363 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.

Jul 17 – 24

G$20,524 GYD per night