Family-friendly vacation rentals in Bolivar

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.

Family · Kitchen · TV

Town Square Cottage | Walk to all of downtown HF

This charming cottage was built in 1837 as the original firehouse of Harper's Ferry. The town square is outside your front door, and it is a short walk to the National Historical Park, restaurants, cafes, and shopping. A perfect blend of location and history, the cottage has many modern updates including queen size bed, pull out couch, fast WIFI, washer/dryer, smart tv, and a secure shed for bike storage. Ladder in the kitchen leads to locked storage area. Living space is all on the first floor.

Family · Kitchen · Sleep quality

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 spaces · Kitchen · Heating

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 spaces · Family · Parking

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 spaces · Kitchen · Shared spaces

Cozy Tiny House in Harpers Ferry Tub & River Views

Pet Free, 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 peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

Indoor spaces · Kitchen · Biking

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Kitchen · Family · Outdoor spaces

Minutes to Downtown Harpers Ferry

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 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: - Roast marshmallows in the Fire Pit - Hiking, Rafting and Tubing just 10 mins away

Kitchen · Indoor spaces · Location

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 spaces · River · Cleanliness

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

BellaRosa at Rose Trellis is a 1840 home with original heart pine floors and real character. The best dining in Harpers Ferry is across the street: Snallygaster's Cafe and Kelly's Farm Kitchen. The Barn has live music throughout the week. We've got plenty of parking, but you won't need your car. The national park, trails, and river are all close by. Harpers Ferry is dog-friendly. Your pup is welcome here, too.

Family · Indoor spaces · Backyard

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.

Indoor spaces · Family · Check-in

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.

Family · Indoor spaces · Pets