Family-friendly vacation rentals in Bolivar

Apartment in Harpers Ferry

The exterior of a contemporary home is showcased, featuring large windows that allow natural light to filter inside. Surrounding the entrance, colorful planters filled with various plants add a touch of greenery to the gravel pathway.

The Boundary House Apartment

Located on this one of a kind spot, the front of the home is considered Historic Harpers Ferry, and the back Historic Bolivar. Either way you look at it you are centrally located within walking distance. On a private road it is not only private, it is quiet. There is a quaint bakery at the top of Boundary Street to the right and to the left there are 2 restaurants, and the local band hot spot. You will find this spot VERY spacious as it is a 1 bed, 1 bath, full kitchen that is almost 1000 sq ft.

KitchenIndoor spacesOutdoor spaces

4.97 out of 5 average rating, 201 reviews

4.94 out of 5 average rating, 221 reviews

The spa-inspired master bath features a freestanding tub with a sleek design, set against a backdrop of rich wooden tile. A wooden stool complements the space, while a glass shower enclosure and minimalist fixtures contribute to a modern aesthetic.

Home in Bolivar

Luxury, Spa tub, movie rm, new AC, best beds ever

Fall colors coming soon (Oct-mid Nov) July 2026 new AC split upstairs. Now has 3 AC systems. You will want to stay...longer. The most comfortable beds ever, and sleep should be priority #1. Our luxury design and furniture is unmatched in the area. And our location is at best end of Washington St. 0.25 miles away. No train noise at this end. Spa master bath/ free-standing tub, relaxing deck. Movie room w/ 92" smart TV. Luxury design (West Elm, CB2, Roche Bobois, etc.). Super Strong mesh WiFi.

KitchenIndoor spacesView

4.92 out of 5 average rating, 230 reviews

A rustic building with a wooden exterior and a red metal roof is set amid lush greenery. A large window beside an entry door is framed by flowering plants, while a stone pathway leads toward a well-maintained lawn and seating area.

Loft in Harpers Ferry

Carriage Suite Location Private Lily Garden BnB

A completely equipped two bedroom vacation rental suite. Located in the Historic District of central Harpers Ferry. The Carriage House is a large unit with private entrance, two beds, full bathroom, and kitchen. The shared yard has a picnic table and swing to enjoy the summer weather. There's internet access & cable television. A good breakfast is included! Come tour American History, hike the Appalachian Trail, bike the C&O Canal, see nature's wonders, and access Washington DC by commuter rail.

Indoor spacesKitchenTV

A living room is presented with a blue sofa and a yellow accent chair. A large world map decorates the wall, complemented by a glass coffee table atop a patterned area rug. Light filters through a window, illuminating the space.

4.94 out of 5 average rating, 111 reviews

Romantic & Charming Home w/foosball walk downtown

This historic three bedroom house is centrally located in scenic Harpers Ferry, walking distance to the Old Town. Sightseeing, white water rafting, kayaking, fishing, hiking, biking, snow tubing and many more activities are only minutes away. From taking a walk to where Shenandoah and Potomac Rivers merge, to hiking the Appalachian Trail, or visiting one of the wineries and breweries in the area, there is something for everyone to enjoy. For civil war buffs there's plenty of sights to visit.

FamilyKitchenGrill

Tiny home in Harpers Ferry

The cabin is nestled among vibrant greenery, surrounded by flowering plants and lush trees. A garden trellis adorned with blooms contrasts with the cabin's rustic exterior, which features a screened porch elevated off the ground. Natural pathways guide the way through the tranquil garden setting.

Retro Tiny Cabin in the Trees

Glamping in Harpers Ferry! Elevated 8' x 16' cabin in a lush garden property surrounded by trees. Full bathroom w/rain showerhead. King bed can be converted to 2 twins if requested. 1940s vintage decor. Minifridge, microwave, toaster, coffeemaker, elec kettle, minigriddle. NO STOVE. Opens to an 8' x 16' screened porch w/ceiling fan, comfy seating, kitchen table & sink. Private spot yet in walking distance to many HF activities & dinner restaurants. Indoor/outdoor living & in-town convenience.

Indoor spacesFamilyNearby

4.97 out of 5 average rating, 614 reviews

A welcoming front porch is seen, featuring two sets of stairs leading to it. Rocking chairs are placed on either side, enhancing the inviting entrance. Two planters with vibrant flowers are visible at the base of the steps, providing a cheerful touch to the home’s exterior.

4.92 out of 5 average rating, 116 reviews

House of Sosia and Alexander in Harpers Ferry

Charming 3-bedroom Vacation Rental with Porch, Backyard, and pet friendly with no fee! The perfect vacation home in Harpers Ferry. A porch with rocking chairs, a swing, and a fenced backyard with a stone patio and fire pit. Just a 5-minute walk from Harpers Ferry’s historic sites, restaurants, trails, and train station, this pet-friendly rental offers parking for two cars. Explore Civil War history, enjoy stunning river views from the nearby footbridge and a 10-minute drive to Shepherdstown.

Indoor spacesKitchenBiking

4.95 out of 5 average rating, 124 reviews

Cozy Fall Duplex Retreat - 1 Mi to Harpers Ferry

"Perfect for Extended Stays!" Cozy retreat! Just 1 mile from historic downtown Harpers Ferry, with a private backyard, fire pit, gas & charcoal grill, private entrance and parking. 1 mile to the Appalachian Trail and the C&O Canal path 1.2 miles to Harpers Ferry Train Station 2.4 miles to Snow Riders 2.9 miles to Harpers Ferry Brewing We have additional listings on the same lot for additional accommodations: https://airbnb.com/h/cheerful-duplex-in-hf https://airbnb.com/h/lovely-cottage-in-hf

Indoor spacesKitchenNearby

Treehouse in Shepherdstown

The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Indoor spacesFamilyOutdoor spaces

4.98 out of 5 average rating, 453 reviews

4.82 out of 5 average rating, 202 reviews

Cabin in Bolivar

Minutes to Downtown Harpers Ferry w/Hot Tub

Built in 1864 and located just a short 10 min. walk from the Shenandoah River. Exposed stone walls and artfully crafted carpentry, add to its many updates and modern furnishings. Unwind in the hot tub while stargazing and enjoy the fresh air while roasting marshmallows. Nearby there are several picturesque wineries only 10 minutes away. Tons of old world charm! The highlights: - Relax in the hot tub! - Roast marshmallows in the Fire Pit - Hiking, Rafting and Tubing just 10 mins away

KitchenIndoor spacesWalkability

4.97 out of 5 average rating, 112 reviews

The exterior of a restored white house is adorned with festive wreaths and a decorative garland. A dark front door is accentuated by holiday decorations, while a patterned pathway leads to the entrance. The scene is framed by greenery and softly lit with lanterns.

Home in Bolivar

Beautiful 4 bedroom home in Historic Harpers Ferry

Built in 1840, this fully restored home off Washington Street in historic Harpers Ferry is the ideal place for your getaway. It is walking distance to restaurants, bars, and shops of Downtown Harpers Ferry. It is an easy walk or bike ride to the Appalachian Trail or the C&O Canal path. Dozens of wineries and breweries are a quick drive/uber/lyft away. After a day of exploring, return to this comfortable home to sit by the fire or make dinner in the gourmet kitchen.

FamilyKitchenHeating

Guesthouse in Harpers Ferry

A charming brick facade features a central circular window and a decorative metal artwork above the entrance. Lush greenery and vibrant flowers surround the entrance, while a two-story yellow building with a porch is visible in the background under a partly cloudy sky.

Between the Rivers Guest Cottage

Between the Rivers Guest house is centrally located in historic Harpers Ferry and walking distance to all shops and restaurants. You will enjoy staying in the towns original "Telephone Building". Take in river views from our front porch and a relaxing outside patio. Walk to the Appalachian trail, go white water rafting, check out a local winery, and tour the vast history that our town has to offer. We look forwarding to having you as our guest!

Indoor spacesViewHiking

4.99 out of 5 average rating, 119 reviews

A modern kitchen features sleek cabinetry and a stainless steel stove. A vibrant green wall with an illuminated neon artwork adds a pop of color. A dining table with metal chairs is positioned against the wall, creating a stylish yet functional space.

4.93 out of 5 average rating, 784 reviews

Eclectic & Romantic - Walk to Historic Downtown!

Eclectic space full of little treasures I’ve picked up during my travels. You will find the place cozy enough for a reset and recharge weekend but also inspiring for gatherings and celebrations. Take advantage of the books, games and excellent SONOS system in the house as well as outside on the patio. This place is great for music lovers and people who enjoy a change from the ordinary.

KitchenFamilyLocation

Popular amenities for Bolivar family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 134 reviews

Chalet in Purcellville

Chalet at Harpers Ferry for Family Gatherings

KitchenFamilyAmenities

4.83 out of 5 average rating, 251 reviews

Historic Home, Hot Tub, Campfire Ring, Hardwood

Indoor spacesKitchenAmenities

A spacious backyard is surrounded by a wooden fence, showcasing a patio area with multiple seating options. A hot tub is visible, along with a fire pit and several Adirondack chairs arranged for gathering. Lush green grass and mature trees enhance the outdoor setting.

4.89 out of 5 average rating, 235 reviews

The Historic Booth House at the Harpers Ferry KOA

FamilyKitchenRiver

4.95 out of 5 average rating, 235 reviews

The cabin exterior is surrounded by trees, creating a natural setting. A welcoming porch features seating and leads into the interior. Large windows allow natural light to illuminate the space, while a gravel pathway connects the home to the surrounding area.

Cottage in Harpers Ferry

Harper's Ferry Tree House/ hot tub / nature/ trees

KitchenIndoor spacesCondition

An aerial view showcases the expansive Potomac River surrounded by lush greenery and rolling hills. The property features a large grassy area leading to the river's edge, set against a backdrop of dense trees and distant mountains.

4.93 out of 5 average rating, 184 reviews

Riverfront HarpersFerry! PrivateDock,HotTub,Kayaks

FamilyKitchenGetting around

A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.

4.97 out of 5 average rating, 136 reviews

Gorgeous cabin on Blue Ridge

KitchenFamilyWifi

5.0 out of 5 average rating, 111 reviews

A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.

Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

KitchenIndoor spacesPool

Tiny home in Harpers Ferry

Romantic & Fun w/Amazing Overlook & Hot Tub

Indoor spacesFamilyDecor

4.96 out of 5 average rating, 216 reviews

Family- and pet-friendly home rentals

Townhouse in Harpers Ferry

Heart of Harpers Ferry: 1800s, Walkable, Dogs OK

KitchenIndoor spacesLocation

4.88 out of 5 average rating, 155 reviews

4.96 out of 5 average rating, 105 reviews

A welcoming living area features a cozy sectional sofa and a round glass dining table with two chairs. Natural light enters from a large window with views of greenery. A small decorative plant and a TV mounted on the wall enhance the space.

Home in Bolivar

Thomas Place

Indoor spacesFamilyCheck-in

The image captures a view of a historic street in Harpers Ferry, lined with red-brick buildings and a mix of metal and shingle roofs. The quiet street features a gentle slope leading into the scenic backdrop of surrounding mountains.

4.98 out of 5 average rating, 101 reviews

Historic home Downtown HarpersFerry

FamilyKitchenCleanliness

4.98 out of 5 average rating, 142 reviews

Cottage in Harpers Ferry

Town Square Cottage | Walk to all of downtown HF

FamilyIndoor spacesTV

4.91 out of 5 average rating, 363 reviews

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

Outdoor Basecamp at Tiny Hidden Ridge

Indoor spacesKitchenParking

Apartment in Harpers Ferry

A dining area is visible, featuring a small round table with two metal chairs. A kitchenette is seen in the background, showcasing cabinets and a countertop with appliances. The room is softly lit, with a patterned rug beneath the table and a view of the bedroom through an open door.

Top o' the Hill Apt. in historic Harpers Ferry

KitchenFamilyAccess

4.94 out of 5 average rating, 160 reviews

Superhost

A spacious mountain retreat is set amongst trees, featuring a warm wooden exterior. The entrance showcases a stone chimney and illuminated porch. The driveway is paved and leads to a two-car garage, providing convenience for guests.

Home in Knoxville

Happy Harbor | Riverside w/ Water Hole + Game Room

FamilyIndoor spacesHiking

4.82 out of 5 average rating, 125 reviews

4.87 out of 5 average rating, 111 reviews

A cozy outdoor area features a circular fire pit surrounded by three red adirondack chairs. The well-maintained lawn is complemented by greenery and a wooden structure with large glass doors. A dog is seen playfully roaming in the yard.

Tiny home in Bolivar

Trailhead Hideaway

KitchenIndoor spacesQuiet

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 641 reviews

An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.

Cabin in Bluemont

Rustic Blue Ridge Cabins

Indoor spacesKitchenRiver

Tiny home in Stephens City

Farm Stay in a luxury tiny home with hot tub

Indoor spacesFamilySleep quality

5.0 out of 5 average rating, 172 reviews

4.95 out of 5 average rating, 290 reviews

A charming outdoor seating area features red wooden chairs and a fire pit, surrounded by lush greenery and pavers. The Cottage, with its welcoming facade and gray metal roof, is visible in the background, offering a cozy retreat in a natural setting.

Cottage in Bluemont

Cottage on Horse Farm: Wineries/Breweries, Horses!

Indoor spacesKitchenOutdoor spaces

4.82 out of 5 average rating, 129 reviews

A wooden deck extends from the cabin, surrounded by lush green trees. A striped awning provides shade over a picnic table, creating a space for outdoor dining or relaxation. The natural ambiance enhances the secluded feel of the property.

Cabin in Keedysville

Quiet Antietam Cabin

Indoor spacesKitchenCondition

Farm stay in Purcellville

A horse stands peacefully in a lush green pasture, surrounded by a black wooden fence. In the background, a well-maintained barn with a cupola is visible, complemented by a clear blue sky and scattered clouds.

The Hunt Box @ Tally Yo Farm

KitchenFamilyWalkability

4.98 out of 5 average rating, 243 reviews

4.95 out of 5 average rating, 427 reviews

A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.

Cottage in Hamilton

*Cottage @ Firefly Cellars* VA Wine Country escape

FamilyIndoor spacesCheckout

4.98 out of 5 average rating, 148 reviews

A log cabin is nestled among the trees, featuring a fenced inground pool in the foreground. The pool area is surrounded by a textured patio, complemented by several wooden chairs positioned nearby. The cabin is situated on a gravel driveway, highlighting its private setting.

Cabin in Fort Valley

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Indoor spacesKitchenGrill