Family-friendly vacation rentals in Jefferson County

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.

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.

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.

Lindas Country Cottage

Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

Tequila Sunset, Harpers Ferry. Entire first floor!

Welcome to Tequila Sunset in Harpers Ferry, WV! This beautiful, secluded home has stunning sunset views, you'll truly feel on top of the world! 100 mile vista of the gorgeous Blue Ridge Mountains. Entire first floor is yours, no shared spaces! Over 1200 SF of room to unplug & relax. King size Nectar bed, cozy indoor wood burning fireplace, outdoor firepit, 84" TV, & a private deck to enjoy the natural surroundings. Just 2 miles from the renowned Mountain Lake Club and the Appalachian Trail!

❤️ 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 2.5 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.

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.

Modern, private cottage at Fairview Organic Farm

Discounts for stays of 5 nights or more. Sitting atop a hill on 23 acres at historic Fairview Organic Farm, Circa 1737, the newish cottage is surrounded by pasture, organic gardens, history & overlooks the Harpers Ferry Gap. We are just a few miles from Charles Town, Harpers Ferry, Shepherdstown, the Hollywood Casino, the Appalachia trail, the Shenandoah & Potomac Rivers, and many historical sites. Enjoy sun rise from the deck and sunsets from the porch.

The Big Room - Historic Schoolhouse

Checkout as late as 8pm on Sundays! Located one mile from the racetrack in the little village of Summit Point. This is a large renovated former classroom with 13' ceilings in the old Elementary School. Summit Point is a quiet place where you can take a leisurely stroll. The Railside Market serves food and sundries one block away. (currently has limited hours) Multiple food options are available in nearby Charles Town and lots more in Winchester Virginia.

The Penthouse in the heart of Downtown Martinsburg

Imagine being downtown near the restaurants, bars, and shopping. Go up 2 flights of stairs and you've arrived in heaven. The breathtaking views from the top floor is memorable. You'll love the light that spreads out through the huge windows! Enjoy the huge king size bed or just hang out in the comfy living room. You are going to make your friends so jealous when they see your pictures!

The GW Hollida Cottage of Shepherdstown

Let time slow just a bit at this unique and tranquil getaway! This recently renovated cottage is situated just behind the GW Hollida house, circa early 1800s. Whether taking a few extra breaths of fresh air on the deck, taking a stroll through the 5 acres of serenity, or kicking back to enjoy some peace and quiet, we are confident you'll love this place as much as we do!

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.