Guesthouse vacation rentals in Western Maryland

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouses in Western Maryland

Guests agree: these guesthouses are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favourite
The kitchen area features a warm wood design with open shelving displaying plates and glasses. A stainless steel sink is accompanied by a dishwasher and a countertop appliance arrangement, including an air fryer and coffee maker. Soft lighting enhances the inviting layout.
Guesthouse in Lovettsville
4.91 out of 5 average rating, 210 reviews

The Patent House

Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen) & full bath upstairs. There is a convertible sofa downstairs (full). Cabin is next door to our house & shares a fence with our pasture where our mini donkeys live. We have yappy dogs and friendly outdoor cats. We're in the country, so bugs make their appearance but they tend to go straight to the window sills.

Top guest favourite
A cozy living area features wooden paneling and a stone fireplace with an active flame. Two deer heads are mounted on the wall. A television is positioned above the fireplace, and small evergreen trees add a touch of nature to the space.
Guesthouse in Fairhope
4.97 out of 5 average rating, 155 reviews

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.

Guest favourite
The exterior of Pond Hill Guesthouse is presented with a welcoming front porch, featuring seating areas and garden beds. A sturdy metal roof covers the structure, and a wooden fence adds privacy. The surrounding landscape includes a grassy yard with seasonal greenery.
Guesthouse in Berkeley Springs
4.97 out of 5 average rating, 376 reviews

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!

Top guest favourite
A stone guest cottage is situated among trees, featuring a well-maintained driveway. Outdoor seating is visible to the right, with a table and chairs positioned for relaxation. The landscape beyond showcases open fields, enhancing the serene countryside ambiance.
Guesthouse in Marshall
4.99 out of 5 average rating, 132 reviews

Moon Hold Cottage - Retreat, Refresh, Recharge

Unplug from city life and venture out to our small organic farm. Spend a night or two in the private guest cottage while enjoying nearby vineyards and restaurants. Spend the day browsing in the local antique shops or relax on the farm and watch nature's display (butterflies, birds, an occasional critter.) We may be working in the garden or putting up hay. We're always glad to share a bit of the harvest when the vegetables are ripe, so you can take some home to enjoy. All are welcome here!

Top guest favourite
A well-appointed kitchen features warm wood cabinetry and a spacious granite countertop. Stainless steel appliances, including a gas range and microwave, are visible. A central island provides additional preparation space, with overhead lighting illuminating the area. Natural light enters from the adjacent room.
Guesthouse in Grantsville
4.98 out of 5 average rating, 138 reviews

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.

Top guest favourite
The exterior of the guesthouse is showcased, featuring a deck with outdoor seating and an umbrella. Tall windows allow for natural light, complementing the green siding. Lush landscaping surrounds the house, creating a natural, inviting setting.
Guesthouse in Smithsburg
4.97 out of 5 average rating, 779 reviews

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.

Top guest favourite
A two-story cottage is set amidst lush greenery, featuring a large upper deck that offers views of the surrounding woods. Colorful azaleas and shrubs enhance the entrance, while a gravel drive leads to the property, surrounded by trees exhibiting signs of spring.
Guesthouse in Myersville
4.94 out of 5 average rating, 255 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Guest favourite
The interior of the cabin features natural wood paneling and high ceilings, creating an open and spacious atmosphere. A full-sized bed is dressed in soft linens, complemented by a decorative rug on the polished wooden floor. Light filters in through two windows, enhancing the serene space.
Guesthouse in Front Royal
4.87 out of 5 average rating, 110 reviews

Cozy Shenandoah River Cabin (10min to Nat’l Park!)

Come get away to our cozy guest cabin, just 10 mins from Shenandoah National Park and a 5 min walk to the Shenandoah River! Perfect for a peaceful stay in a gorgeous natural setting. High ceilings, open concept, wood panelling and a private enclosed patio. Close to vineyards, breweries and outdoor attractions. (Please note, there isn't a full kitchen) If you have more than 3 guests, please let us know. We have a second cabin on the property that we can offer as an additional space.

Top guest favourite
The timber-framed chalet is surrounded by vibrant flower gardens, showcasing various colorful blooms. Large windows and a balcony enhance the exterior, framed by trees creating a natural backdrop. A patio area with seating is visible in the foreground, inviting guests to enjoy the peaceful surroundings.
Guesthouse in Hamilton
4.99 out of 5 average rating, 156 reviews

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.

Top guest favourite
The Alton Cottage showcases a quaint exterior featuring a wooden deck and stone steps leading up to the entrance. Surrounded by green grass and trees, the weathered stone chimney from the original structure is partially visible, adding a historic touch to the peaceful landscape.
Guesthouse in Warrenton
4.97 out of 5 average rating, 337 reviews

The Alton Cottage -a luxury country retreat

The Alton Cottage is a charming, newly refurbished 1820s guest house- formerly a summer kitchen to the original farm house. Views are of rolling fields and their bovine occupants. We are within 30 minutes of almost 20 wineries and another 20 breweries, 5 min to Airlie, and only 5 mi to Old Town Warrenton. We are also close to several antique stores, farmers markets and Shenandoah National Park. We strive to make every guests stay special.

Guest favourite
A bright studio space features a queen size bed adorned with white linens. A TV mounted on the wall is visible, along with an air conditioning unit positioned by the window. A compact kitchen area is present, highlighted by a green bar and coffee station. Two chairs and natural light contribute to the inviting ambiance.
Guesthouse in Maurertown
4.85 out of 5 average rating, 279 reviews

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

Newly renovated detached studio guest-suite located in the beautiful Shenandoah County with country feels and easy access to I81. It features a butcher block bar for eating/working, a queen size bed, tv with Netflix along with Chromecast so you can cast your favorite shows from your phone/laptop, and during the summer you'll have the quietest and smart ac unit on the market. It has a shared driveway with the host's primary residence.

Top guest favourite
The guesthouse's exterior features sturdy stone walls and a green metal roof. White window shutters enhance the classic design. A covered porch provides a welcoming entrance, while lush green grass and neatly trimmed hedges surround the building. Scenic views of the property are visible in the background.
Guesthouse in Flint Hill
4.96 out of 5 average rating, 142 reviews

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.

Popular amenities for Western Maryland guesthouses

Destinations to explore