Guest house holiday rentals in Western Maryland

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.

A Hidden Jewel in Loudoun County, Virginia

This charming 5000 sqft huge single family guest house is located just off of Route 7 in the historic town of Hamilton, VA. Enjoy a cup of coffee on the back deck while relaxing in a country environment. Take a walk in a beautiful rural area with magnificent view over the countryside or Enjoy a bike ride on the former W&OD Railroad, which is sitting just outside the house. Listing is for the two upper floors. Access between the basement and the upper floors is locked and secured at all times.

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.

Cozy cottage nestled on 8 acres with mountain view

Relax and enjoy this cozy, yet luxurious space! Enjoy Mountain Views at sunrise and sunset. Besides the resident horses, you will enjoy seeing deer, rabbits, raccoons and many others. We are located a very short drive from Seven Bends State Park, the Shenandoah River and Muse Winery….as a matter of fact, you could walk! Located within minutes of everything, we are also close to Civil War museums/Historic sites, natural caverns and caves, etc. I may even bake for you, if you’re lucky!!

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.

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.

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.