Holiday rentals in Charles Town

The Big Room - Historic Schoolhouse

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. There are even a couple sidewalks ;) We have 3 churches and a post office. 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!

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!

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.

Spacious 2nd Floor Retreat in Charles Town

Escape to our spacious 2nd-floor retreat, ideally located just a short walk from charming shops and eateries in town. Centrally situated near main thoroughfares, our apartment offers the perfect blend of convenience and comfort. Unwind in our inviting living space, complete with ample natural light and modern amenities. Rest easy with safe and secure parking available onsite, ensuring a worry-free stay. Experience the best of local living with everything you need right at your doorstep!

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

Beautiful Happer Ferry

visitors drawn to the nearby Hollywood Casino, historic downtown, and local attractions. Freshly Updated Throughout — New luxury vinyl plank flooring, fresh paint, a stunning kitchen with shaker-style cabinets, quartz countertops, and stainless-steel appliances. ✨ Charming Sunroom & fully fence Private Backyard Retreat — . ✨ Prime Location — Just minutes to the Casino, downtown Charles Town, local parks, shops, and dining — and an easy commute to Northern Virginia andDC.

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.

Last Rodeo Cottage

Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

Historic Charles Town Home. Centrally Located

Access all that Charles Town has to offer from this 4-bedroom, 2-bath home. Includes a full kitchen, Smart TVs, loft, a screened porch, and more. Grill on the deck or play board games indoors. Explore the historic downtown or nearby Harpers Ferry as well as various vineyards and breweries nearby! 1 Mile from Charles Town Casino.