Guesthouse holiday rentals in Western Maryland

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Top-rated Guesthouses in Western Maryland

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

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Top Guest favourite
An open living space features wooden beams overhead and warm brown flooring. A cozy seating area is paired with a light-colored sofa. A Christmas tree adds a festive touch, while a kitchenette with cabinetry is visible in the background, accompanied by a dining table and chairs.
Guesthouse in Grantsville
4.95 out of 5 average rating, 178 reviews

“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.

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
4.92 out of 5 average rating, 214 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, 156 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.

Top Guest favourite
The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.
Guesthouse in Middleburg
5 out of 5 average rating, 99 reviews

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

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, 379 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 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, 140 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, 782 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.

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, 157 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, 339 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
4.97 out of 5 average rating, 146 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.

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