Family-friendly holiday rentals in Bolivar

Find and book unique family-friendly homes on Airbnb

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 favourite
A cozy tiny home is surrounded by lush greenery. Outdoor seating is provided with a small table and chairs, while planters filled with flowers enhance the space. A soaking tub is visible on the patio, adding to the charm of the outdoor area.
Tiny home in Harpers Ferry
4.96 out of 5 average rating, 179 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Quiet away from the train in old town Large patio, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Top guest favourite
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
4.92 out of 5 average rating, 223 reviews

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.

Top guest favourite
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.
Tiny home in Harpers Ferry
4.97 out of 5 average rating, 575 reviews

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.

Top guest favourite
A living area features a comfortable beige sofa and an adjacent dining table with two chairs. A small desk with a chair and laptop is positioned nearby. Sunlight enters through a window adorned with white blinds, illuminating the relaxed atmosphere.
Home in Bolivar
4.97 out of 5 average rating, 318 reviews

Day Street - Walk to Harpers Ferry NP

This stylish apt with fenced yard is located just mins to the HFNP Park. 24/7 convenient store just 1 block away; library across the street; a corner lot in a very quiet neighborhood. Perfect place to start your hikes or just to rest for the weekend. The home has 1 BR, kitchen, full bath and coffee bar - Keurig; coffee pot; coffee press; pour over coffee; beans and grinder; teas bags w/ water pot and private parking for our guests. Please note that the living area for this home is upstairs.

Top guest favourite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
5 out of 5 average rating, 275 reviews

Luxury Mountain Getaway: Sunsets, Wines & Views.

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Superhost
A charming tiny house is set among greenery, featuring a red tin roof and welcoming porch. A new wooden staircase leads to the entrance, bordered by planters with colorful flowers. Surrounding foliage creates a serene, natural environment.
Tiny home in Jefferson County
4.88 out of 5 average rating, 497 reviews

❤️ Secluded 1940s Romantic Tiny House on the River

Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 3 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

Top guest favourite
The vibrant exterior of the cottage is framed by colorful flowers in bloom. A spacious deck is showcased, complete with a bright red umbrella. Light green siding and large windows reflect the sunny atmosphere, blending harmoniously with the natural surroundings.
Flat in Harpers Ferry
4.98 out of 5 average rating, 241 reviews

A little piece of the country in the town

Located in the scenic town of Harpers Ferry, this sunny little cottage is tucked away in a great little neighborhood full of friendly people and backyard chickens. The neighborhood has restaurants, a wonderful bakery, two local bars, and we are a 20 minute walk from historic Harpers Ferry. The cottage is owned by two local old time Appalachian musicians, so you might hear some fiddle tunes drifting through the air if you are deck sitting. Bedroom has a queen bed No cleaning fees

Top guest favourite
The exterior of the cottage features a classic white facade with black shutters and a large star ornament above the entrance. Well-maintained landscaping includes small shrubs and a stone walkway leading to the door, set against a backdrop of open green fields and trees.
Guest house in Lovettsville
4.96 out of 5 average rating, 240 reviews

Cottage Escape in Virginia Wine Country

Tucked among rolling hills, this cozy cottage rests on 25 acres with a private lake just beyond your door. Sip wine beneath the stars, paddle at sunrise, or wander where the wildflowers grow. Just minutes from vineyards, brews, and historic charm, it's a perfect escape to slow down and reconnect. You may hear the laughter of our little ones nearby—just part of the magic here at the farm. We can't wait to welcome you.

Guest favourite
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.
Home in Harpers Ferry
4.93 out of 5 average rating, 712 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.

Top guest favourite
A restored log cabin features a red metal roof and wooden exterior, framed by trees and a grassy area. A dog lies comfortably on the ground in front of the porch, which is adorned with red chairs and a lantern.
Cabin in Shepherdstown
4.96 out of 5 average rating, 517 reviews

The Log Cabin

A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Guest favourite
A welcoming living area showcases two comfortable couches adorned with decorative pillows, accompanied by a round coffee table at the center. Soft lighting is provided by a standing lamp, and a colorful area rug enhances the wood-like flooring. A wall sign adds character to the space.
Guest suite in Bolivar
4.96 out of 5 average rating, 195 reviews

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.

Top guest favourite
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.
Flat in Harpers Ferry
4.99 out of 5 average rating, 435 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.

Popular amenities for Bolivar family-friendly rentals

When is the best time to visit Bolivar?

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Avg. price$278 SGD$265 SGD$278 SGD$316 SGD$278 SGD$307 SGD$332 SGD$278 SGD$261 SGD$278 SGD$278 SGD$274 SGD
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Quick stats about holiday rentals that are family-friendly in Bolivar

  • Total holiday rentals

    Explore 30 holiday rentals in Bolivar

  • Nightly prices starting at

    Bolivar holiday rentals start at $164 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,810 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Bolivar holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bolivar rentals

  • 4.9 Average rating

    Bolivar stays are highly rated by guests – averaging 4.9 out of 5!