Guest house holiday rentals in Western Maryland

“The Loft” Guest House w/wifi workspace, gym etc

This unique two story guest house has a style all its own. The Loft has one bedroom upstairs along with a great workspace with excellent WIFI, full size bathroom and closet and a small kitchenette including microwave, fridge, air fryer and Keurig. Room darkening curtains, AC, TV w/Roku, full bath/shower unit, pullout sofa and queen size bed all in a very large and open floor plan! The first floor is set up as a gym/workout room. Ample and easy parking. Use of the outdoor patio area. Adults only.

Mountain View Acres Getaway

Enjoy nature in a beautiful peaceful setting with 100 acres of privately owned property. Breathtaking panoramic views spanning 45 miles in a tranquil natural spot with hiking trails throughout. Handicap accessible. Within a short drive of 2 major ski resorts, the Flight 93 Memorial and 2 wineries. Several restaurants and a brewery also within a 15 minute drive. The property includes an outside firepit that is a favorite place for guests to relax and enjoy the breathtaking views of the mountains.

Pond Hill Guesthouse- 2 Bedroom w/Hot Tub & WiFi!!

Reserve two get the third (Sun-Thur) night free! Set among the rolling hills near Berkeley Springs, WV, Pond Hill Guesthouse has everything you'll need. Perfect for stargazing! This guesthouse has a private drive and plenty of privacy. Relax in the hot tub or by a fire and enjoy the stars. Lots of room for couples or small families. WiFi provided. This beautiful guesthouse is owned, and hosted a by local superhost, Doug. Pond Hill is great place to enjoy a piece of West Virginia Heaven!

Countryside getaway 5 min. from Old Rag parking!

Just 5 min away from Old Rag trailhead in Shenandoah National Park and merely minutes from wineries/breweries. Our guest house is close to White Oak Canyon, Skyline Drive, Three Blacksmiths, Washington, and Luray Caverns! Book here if you like: -Escaping the hustle and bustle, and relaxing in nature -Hearing birds sing while sipping coffee/tea/wine on the porch -Observing wildlife (including our chickens and bees) -Fishing on the Hughes River in our backyard -Stargazing and spotting fireflies

Private 2 King BR, 1 BA Apartment Near Wineries!

Fox Farm Apartment is a private country retreat, located on 10 acres, on a quiet, private road. It has 2 king bedrooms, one bath, with incredible views (the sunsets are amazing) and filled with natural light. It has a private entrance w/ staircase to 2nd floor. The bath has a luxury shower and dual vanities. It has a full kitchen stocked with cookware, Direct TV, and large family room. Very close to Leesburg and local wineries and breweries. Linens and towels, soaps, shampoos are included.

Yoder School Guest House with wifi and hot tub

Built originally in the late 1800's and renovated by us in 1991, Yoder School became our home. In later years we converted part of the building into this peaceful getaway. Opportunities for outdoor activities abound. Fantastic road cycling with Strava routes start right here! Just a short drive away great mountain biking, hiking, cross country and downhill skiing, and white water rafting are yours to enjoy. Several unique and popular restaurants, and tennis and basketball courts are nearby.

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's Guesthouse is the perfect get-away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Trailside Chalet (A storybook chalet with hot tub)

The Trailside Chalet is situated on the W and OD Trail, halfway between Leesburg and Purcellville, Va - an ideal base location for visiting wineries, breweries, and the pastoral countryside of Loudoun County. The chalet will put you just steps from the trail for walking/cycling/horseback riding. Relax and enjoy the amenities of one-of-a-kind interior including wood burning fireplace and peaceful surroundings with hot tub. A perfect getaway for a couple or family.

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Trillium Acres Guest House

Located 10 miles from downtown Morgantown and the stadium. Cooper's Rock is just 12 miles away, with hiking, mountain biking and rock climbing. Our cozy house with modern amenities can accommodate 6 people with 2 queen beds, 1 twin and a queen pull-out sofa. Trillium Acres Cottage and Trillium Acres Hilltop are next door and a short walk through the woods for larger groups needing more space.

Skyhorse Retreat Guest House

In the middle of VA wine country and only minutes to three Appalachian Trail trailheads. Located 45 miles west of Washington D.C., on a 10-acre property on top of the Blue Ridge Mountains. Private guesthouse (built Jan 2020) with a large deck overlooking trees. The Guest House sleeps 4, has a full kitchen, and access to a Hot Tub at the main house. Breakfast items and snacks included.

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.