Family-friendly vacation rentals in Bolivar

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Top-rated family-friendly rentals in Bolivar

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

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Guest favorite

The living area features a pull-out futon in front of a patterned area rug. Two wooden chairs are positioned at a small table beside a large window, with a vibrant artwork depicting a barn mounted on the wall. A kitchenette area is visible in the background.

Home in Knoxville

4.91 out of 5 average rating, 347 reviews

Outdoor Basecamp at Tiny Hidden Ridge

Our basecamp apartment is perfect for the outdoor enthusiast looking for an escape to the countryside. We are 1/2mile from the C&O Towpath and Potomac river and less than 2 miles from Harpers Ferry and the Appalachian Trail. Our location makes this perfect for couples, families or groups looking to hike, bike, or raft. Make use of our deck, grill, fire pit, and bike tools. We recently got internet. But no TV, and weak cell signal. The kitchenette has a hotplate, toaster oven, and coffee maker.

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, 660 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

The exterior of a rustic barn-style structure is shown, featuring weathered wooden siding and a red metal roof. Lush greenery surrounds the building, and a stone pathway leads to a small patio area with seating. Natural light creates a welcoming ambiance.

Apartment in Harpers Ferry

4.9 out of 5 average rating, 158 reviews

Trundle Private Suite Location Lily Garden BnB

An efficiency one bedroom vacation rental suite. Located in the Historic District of central Harpers Ferry. The Trundle is a cozy economy unit with private entrance, queen size bed, bathroom, and kitchenette. The shared yard has a picnic table and swing to enjoy the summer weather. There's internet access & cable television. A hearty breakfast is included! Come bike the C&O Canal, tour American History, hike the Appalachian Trail, see nature's wonders, and access Washington DC by commuter rail.

Superhost

Home in Knoxville

4.79 out of 5 average rating, 125 reviews

Escape from the city. Farmhouse Near Harpers Ferry

Secluded Country Retreat Near Harpers Ferry 3BR | 2BA | Private Trails | EV Charging | 100+ Acres Escape to a peaceful retreat on 100+ acres of pristine countryside, minutes from Harpers Ferry, Shepherdstown, and the C&O Canal. This secluded 3-bedroom, 2-bath home blends modern comfort with rustic charm, perfect for families, couples, and outdoor enthusiasts. Enjoy private trails and nature at your doorstep. Events are allowed in a separate indoor/outdoor event space available for rent.

Top guest favorite

The exterior of the guesthouse is showcased, featuring a deck with outdoor seating and an umbrella. Tall windows allow for natural light, complementing the green siding. Lush landscaping surrounds the house, creating a natural, inviting setting.

Guesthouse in Smithsburg

4.97 out of 5 average rating, 742 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's 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

A serene countryside view showcases a spacious green lawn bordered by trees and hills in the background. Two houses are visible: one with a wraparound porch and the other a smaller structure. An organic garden is seen in the foreground, framed by a simple fence.

Guesthouse in Keedysville

4.98 out of 5 average rating, 212 reviews

City Dog Farm

Comfortable, light-filled one bedroom apartment on 10 acres in Maryland near Antietam battlefield and Harpers Ferry, WV. We have chickens, an organic garden, hills, woods and a stream. Apartment is 15 minutes from Harpers Ferry, Antietam battlefield, the C&O canal, river rafting on the Potomac or Shenandoah, vineyards, the Appalachian trail and small towns including Boonsboro and Shepherdstown, WV. 30 minutes to Frederick or Hagerstown/1.5 hours to DC or Baltimore. SORRY NO PETS

Guest favorite

Two chairs are positioned near a campfire ring on a grassy area, surrounded by trees. A gently sloping hill leads down to a pond, with a wooden fence visible in the distance. Sunlight filters through the leaves, creating a shaded and inviting space.

Guesthouse in Purcellville

4.81 out of 5 average rating, 274 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 with the exception of Wi-Fi - no satellite or TV. 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).

Top guest favorite

A panoramic view captures rolling hills covered in autumn foliage, with vibrant reds and oranges visible on the trees. A green tractor and a dark pickup truck are parked on the grassy area, which leads toward the distant mountains under a soft sky.

Farm stay in Knoxville

4.97 out of 5 average rating, 283 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, 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.

Top guest favorite

A charming multi-story home features a light-colored wooden exterior, complemented by stone pathways and a staircase. Flags adorn the exterior, and a spacious deck area is visible, surrounded by greenery. The building's architectural details showcase a blend of historical and modern design.

Home in Harpers Ferry

4.94 out of 5 average rating, 397 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.

Guest favorite

A spacious two-story home is depicted, featuring a classic white exterior and a welcoming front porch. Lush greenery surrounds the building, and a gravel path leads to the entrance, contributing to the property's inviting appearance.

Home in Harpers Ferry

4.89 out of 5 average rating, 117 reviews

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient

Yes, the HOT TUB is OPEN! We have 4 other nearby full vacation rental homes in Harpers Ferry and have been hosting visitors since 2011. Conveniently located in a semi-rural neighborhood setting with large yard, hot tub, fire pit and large field in the back. The home has cable internet and wifi and free off-street parking.

Top guest favorite

An open living area features a cozy seating arrangement with a dark leather couch and a stylish futon. A glass coffee table sits in the center, while natural light pours in from a large window, illuminating the space. A wall-mounted TV and a fireplace are also visible.

Apartment in Harpers Ferry

4.99 out of 5 average rating, 407 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.

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.