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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Top guest favorite

A spacious sleeping area is centered around a beautifully made bed with a textured gray coverlet. Nightstands on either side feature stylish lamps and small potted plants. Art is displayed on the wall, contributing to a serene atmosphere, with natural light filtering through the window.

Guest suite in Shepherdstown

4.96 out of 5 average rating, 661 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.

Superhost

A well-maintained golf green is visible, featuring a flag tucked into the short grass. The area is surrounded by a sand trap on either side, with the community name, 'The Woods,' clearly displayed in the grass. Nearby trees provide a natural backdrop.

Cabin in Hedgesville

4.98 out of 5 average rating, 41 reviews

Hawk's Nest at The Woods

This West Virginia chalet-style cabin is a perfect rustic getaway with plenty of modern amenities. Nestled in the Appalachian Mountains, it is less than a 2-hour drive from DC and Baltimore (2.5 hours from Pittsburgh)—close enough to get there quickly, but far enough to feel like a whole different world. As part of The Woods community, enjoy a massage at the full-service spa or opt for a day on the links with two beautiful courses to choose from (36 holes). Or, make a fire, chill out and relax!

Guest favorite

A two-story home with a covered front porch is surrounded by leafy trees and a well-maintained lawn. Rocking chairs and potted plants set a welcoming atmosphere, inviting relaxation. The pathway leads to the entrance, complemented by sunlight filtering through the branches.

Home in Charles Town

4.89 out of 5 average rating, 130 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

The living room features a dark couch and a patterned accent chair, complemented by light hardwood flooring. A coffee table is centered between the seating area, and a television is positioned on a console against the wall. Natural light enters through two windows, covered with dark curtains.

Condo in Charles Town

4.73 out of 5 average rating, 120 reviews

2 Bed Condo at Abolitionist Ale Works #300

Beautiful historic renovation in the heart of Downtown Charles Town above the brewery Abolitionist Ale Works. This third floor unit is within walking distance to some of the best bars, restaurants and shops in the area. Features include a renovated kitchen w eat in table, concrete countertops, coffeemaker, microwave, fridge and range, bathroom with clawfoot tub and victorian hex tile, 2 full bedrooms with queen beds and a private washer and dryer and rear balcony

Superhost

A charming cabin is nestled among trees, featuring a sloped roof and large glass windows that offer abundant natural light. A wraparound deck provides outdoor space, while a cylindrical chimney and air conditioning unit are visible on the exterior.

Cabin in Hedgesville

4.88 out of 5 average rating, 225 reviews

Deer Crossing at The Woods

This WV cabin is a perfect mixture of rustic charm and and modern convenience — a great option for families or friends looking for a place to get away. Nestled in the Appalachian Mountains, it is less than a 2-hr drive from DC and Baltimore (2.5 hrs from Pittsburgh)—close enough to get there quickly, but far enough to feel like a whole different world. Enjoy a massage at the spa, play golf, go for a hike, or just fire up the hot tub, chill out, and relax!

Top guest favorite

A charming stone cottage with a wooden front porch features a sloped roof and a brick chimney. Surrounded by trees, the cottage is set on a grassy area, providing a sense of seclusion. Large windows and a welcoming entrance enhance the exterior appeal.

Cottage in Winchester

4.97 out of 5 average rating, 498 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.

A two-story townhome is showcased, featuring a brown exterior with wooden steps leading to the entrance. Lush green grass and well-maintained shrubs frame the pathway, while tall trees provide a natural backdrop, enhancing the peaceful surroundings.

Townhouse in Hedgesville

4.89 out of 5 average rating, 64 reviews

Cozy Townhome At The Woods Resort Golf,SPA,Tennis

This Townhome only 90 miles from NVA located at The Woods Resort which has 2 award winning golf courses, spa, outdoor/indoor pools, hiking trails on Sleepy Creek Wildlife Management Area, indoor/outdoor tennis and a Clubhouse Grill & Pub where you can get bite to eat and drink. Has central AC/Heat, flat screen TV, internet, and wood fireplace. Also a short distance from Sylvan Lake where there is catch & release fishing.

Superhost

The cabin, surrounded by lush trees, features a rustic wooden exterior with a sloped roof. A screened porch is visible at the front, with steps leading up to the main entrance. A gravel area provides parking space amidst the greenery.

Home in Hedgesville

4.68 out of 5 average rating, 56 reviews

Woods Song: Hot Tub | Fireplace | Golf |Pool Pass

If you’re looking for a place that feels like a gentle exhale, Wood Song might be calling your name. Nestled deep in the Woods Resort and shaded by tall, whispering trees, this cozy two-bedroom cottage is all about simple pleasures—hot tub nights, fire-warmed mornings, and that sweet stillness you only get in the woods.

Superhost

A modern cabin, nestled among tall trees, features a green exterior with a red front door. Surrounding foliage and fallen leaves indicate a serene, natural setting, while the cabin’s porch offers a welcoming entrance into the woods.

Home in Hedgesville

4.61 out of 5 average rating, 31 reviews

Country Comfort -wifi, fireplace, golf, rec center

Tucked away in the peaceful landscape of Hedgesville, WV, Country Comfort is exactly what the name suggests—a warm and welcoming escape from the everyday. Whether you're craving a quiet retreat or a weekend of adventure, this single-level home offers the perfect balance of comfort and convenience.

Superhost

A private hot tub is positioned on a wooden deck, surrounded by lush green trees. A scenic view of the mountains and sky provides a tranquil backdrop. The deck features a small chair, emphasizing the quiet and relaxing atmosphere.

Home in Hedgesville

4.84 out of 5 average rating, 61 reviews

Above Sleepy Hollow - Deck, Hot Tub, Wifi, Pets

Tucked away at the peak of Sleepy Creek Mountain, Above Sleepy Hollow is where adventure meets serenity. This cozy cabin is perfect for anyone who feels most at home in the great outdoors—whether you're here to hike, fish, or simply soak in the mountain views from your private rooftop overlook.

Guest favorite

A cozy studio apartment is featured, with a queen bed positioned near a window draped in light curtains. An open kitchen area displays wooden cabinetry and modern appliances. A small dining table with two stools is adjacent to the kitchen, while a television is visible across from the bed.

Farm stay in Shenandoah Junction

4.94 out of 5 average rating, 168 reviews

Historic Rockdale Private Studio Apartment

Private cozy studio apartment. Sunny porch. Custom kitchen. Bathroom with heated floor and huge shower with two shower heads. Full sized Washer and Dryer. Starlink internet. Roku Smart TV in unit. On 24 acre tree farm with sweet GOATS, wildlife, and walking paths.