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.

Three Meadows Farm, outdoor views, great location

As you approach the driveway on the private lane, you'll be welcomed by beautiful meadows and rolling hills. Set on 10 acres in a shaded, forest of mature trees it's comfortable year round. There are beautiful mountain views from several locations on the property. It's peaceful and quiet here most of the time. We're conveniently located just minutes from Flint Hill, not much farther to Washington VA, Sperryville and Front Royal. It's a two bedroom/one bathroom apartment above a detached garage.

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

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.

Peggy's Guest Hideaway

A very quiet and peaceful mobile home / guest house located in Connellsville Pennsylvania. We are close to many popular sites such as the Great Allegheny Passage bike trail and the Laurel Highlands. If you are looking for a place to unwind or just a place to get away for awhile and do not care for hotels or people drama at the end of the day then this place is a good fit. In the evenings the crickets are the loudest noise in the air and many mornings there is deer in the yard.

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.

Summer kitchen guesthouse at Caledonia Farm 1812

Summer kitchen guesthouse built of stone in 1812 and located on a 115 acre free-range cattle farm on the National Register of Historic Places. The first floor is a living room with the original cooking fireplace and a kitchenette. Upstairs is a loft bedroom and bath. Housekeeping is provided on Monday and Friday mornings. Enjoy the peace and quiet, dark skies, scenic views, adventure, and culinary excellence of Rappahannock County.

Studio along i81: Near Wine, Beer, Hiking & Nature

Enjoy recently renovated detached studio guest‑suite in beautiful Shenandoah County—perfect for a peaceful getaway with quick access to I‑81. Inside, you’ll find a queen‑size bed, a butcher‑block bar for meals or work, and a smart AC unit that’s the quietest on the market. Your entertainment will be hassle‑free with a TV (Netflix & cast support), and you’ll have a full guest‑suite and yard (≈1 acre) to call your own.

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.