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.

Indoor spacesKitchenCondition

4.96 out of 5 average rating, 198 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.

4.94 out of 5 average rating, 221 reviews

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.

Indoor spacesKitchenHeating

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.

KitchenIndoor spacesRiver

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.

KitchenIndoor spacesQuiet

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.

KitchenFamilyLayout

4.97 out of 5 average rating, 613 reviews

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

FamilyKitchenLaundry

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 spacesKitchenCheck-in

4.98 out of 5 average rating, 453 reviews

4.82 out of 5 average rating, 201 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

FamilyKitchenQuiet

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.

4.97 out of 5 average rating, 112 reviews

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.

FamilyKitchenView

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, 783 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.

FamilyKitchenCleanliness

Farm stay in Harpers Ferry

A serene body of water reflects shades of turquoise and green, bordered by rocky cliffs and lush trees. Three caves are visible along the rocky shoreline, inviting exploration amidst the peaceful natural surroundings.

Apartment on Peace Ridge Farm

Enjoy a relaxing stay on our family friendly farm, dogs welcome too! You will get to interact with many farm animals. We have a playground in a fenced area, fire pit and gas grill. Our place is close to Historic Harpers Ferry, Shepherdstown, Antietam, Wineries, Shenandoah and Potomac rivers, art and culture, restaurants and family-friendly activities are all within a short drive.

Indoor spacesFamilyQuiet

4.96 out of 5 average rating, 293 reviews

4.97 out of 5 average rating, 214 reviews

Guest suite in Bolivar

Battlefield Bunker

Soak up the charm in this newly finished space. The property has a private entrance, features 2 bedrooms, 1 bath, kitchen, and is approximately 1,096 sf. There is a common area featuring a patio,fire pit, and playground for the littles. Historic Harpers Ferry is 1.3 miles away and the Bolivar Battlefields are less than a mile.

Indoor spacesKitchenSleep quality

Popular amenities for Bolivar family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A single-story house is shown amidst a well-maintained yard featuring a variety of blooming plants. The wood-sided exterior is complemented by a welcoming front porch with a railing, leading to a front door framed by large windows.

4.93 out of 5 average rating, 100 reviews

House of Ruslan Cozy 3-Bedroom Home Sauna/Hot Tub

KitchenFamilyBathroom

4.99 out of 5 average rating, 134 reviews

Chalet in Purcellville

Chalet at Harpers Ferry for Family Gatherings

KitchenFamilyLong stay

4.83 out of 5 average rating, 251 reviews

Historic Home, Hot Tub, Campfire Ring, Hardwood

Indoor spacesFamilyOutdoor spaces

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

Indoor spacesKitchenPets

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

FamilyIndoor spacesCheckout

The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.

4.96 out of 5 average rating, 220 reviews

Historic Farmhouse | Heated Plunge Pool, Billiards

KitchenFamilyParks

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

KitchenFamilyView

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

Indoor spacesKitchenComfort

Family- and pet-friendly home rentals

Townhouse in Harpers Ferry

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

Indoor spacesFamilyPets

4.88 out of 5 average rating, 154 reviews

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

KitchenIndoor spacesPets

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.

4.96 out of 5 average rating, 104 reviews

Thomas Place

FamilyKitchenPets

4.91 out of 5 average rating, 362 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

KitchenFamilyHospitality

4.84 out of 5 average rating, 234 reviews

A well-maintained grassy area is surrounded by lush trees, providing a serene backdrop. A stone structure with a sloped roof is visible to the side, complementing the natural landscape. A wooden fence accents the property, enhancing the sense of seclusion.

Cottage in Purcellville

Stone School House - Minutes from Harper's Ferry

FamilyKitchenPets

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

Indoor spacesKitchenNearby

4.98 out of 5 average rating, 281 reviews

The view captures the farmhouse exterior, showcasing a stone and plaster combination with a dark metal roof. Lush green vines climb the walls, and a spacious deck is visible. Surrounding gardens and pathways enhance the inviting landscape under a clear blue sky.

Farm stay in Hamilton

Ballenger Farm

FamilyIndoor spacesQuiet

5.0 out of 5 average rating, 202 reviews

A charming two-story cottage features a welcoming front door framed by decorative shutters and flower planters. A covered porch is seen to the left, adding outdoor space for relaxation. The surrounding yard is well-maintained, providing a pleasant view of the greenery.

Cottage in Shepherdstown

The Creekside Cottage: Downtown | Pet-Friendly

FamilyKitchenCheckout

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 640 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

KitchenFamilyWalkability

4.95 out of 5 average rating, 289 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 spacesFamilyHeating

4.98 out of 5 average rating, 147 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

FamilyIndoor spacesBackyard

4.95 out of 5 average rating, 426 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

Indoor spacesFamilyHospitality

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

Indoor spacesFamilyCheckout

4.98 out of 5 average rating, 243 reviews

Tiny home in Stephens City

Farm Stay in a luxury tiny home with hot tub

Indoor spacesFamilyAmenities

5.0 out of 5 average rating, 170 reviews

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

KitchenIndoor spacesWifi