Guesthouse holiday 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.

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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

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.

ValueFamilyHiking

4.97 out of 5 average rating, 223 reviews

Guest favourite

A spacious common area features a red couch and an antique-style chair, complemented by a wooden dining table with four chairs. Skylights introduce natural light, while two ceiling fans provide air circulation. A television is positioned across from the seating area, enhancing relaxation.

Guesthouse in Flint Hill

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.

LocationValueWalkability

4.95 out of 5 average rating, 196 reviews

Superhost

The front of a spacious two-story brick home is showcased, featuring a well-manicured lawn with neatly trimmed grass. A large tree and colorful shrubs accentuate the landscape, while windows and a welcoming front door contribute to the home's inviting appearance.

Guesthouse in Hamilton

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.

LocationFamilyBackyard

4.82 out of 5 average rating, 113 reviews

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

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.

ValueLocationSleep quality

5.0 out of 5 average rating, 140 reviews

Top Guest favourite

Guesthouse in Frederick

Private Woodland Retreat | Near Downtown Frederick

Escape to a beautiful one-bedroom retreat. The guesthouse has a queen bed, kitchenette, luxurious bathroom with two shower heads, including a rain head, and a queen pull-out sofa bed. Nestled in the woods with a covered porch for morning coffee, yet a short drive to downtown Frederick, Civil War sites, Frederick Watershed with hiking and cycling trails, Mount St. Mary’s University, Cunningham Falls, and Catoctin. Free WiFi, and Smart Roku TV’s. Parking for 2 cars is included. Dogs are welcome.

FamilyValueDecor

4.96 out of 5 average rating, 100 reviews

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

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.

FamilyLocationHospitality

4.98 out of 5 average rating, 168 reviews

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

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.

ValueFamilyCheck-in

4.97 out of 5 average rating, 859 reviews

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

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.

FamilyLocationCondition

4.88 out of 5 average rating, 126 reviews

Guest favourite

Two chairs are positioned near a campfire ring on a grassy area, surrounded by trees. A gently sloping hill leads down to a pond, with a wooden fence visible in the distance. Sunlight filters through the leaves, creating a shaded and inviting space.

Guesthouse in Purcellville

Barn Apartment in VA Wine Country

Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged with the exception of Wi-Fi - no satellite or TV. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

LocationValueCheckout

4.81 out of 5 average rating, 290 reviews

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

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.

FamilyLocationView

4.96 out of 5 average rating, 183 reviews

Guest favourite

A side view of the home reveals a light blue exterior with large windows, surrounded by a lush green lawn. A wooden picnic table is situated on the grass, offering a space to enjoy the outdoors under the shade of a nearby tree.

Guesthouse in Cumberland

The Hidden Tree

Nestled in the heart of Cumberland. Our cozy home offers a perfect blend of comfort and convenience for your stay. Whether you're here for business or leisure, we've got you covered! Conveniently located near UPMC Hospital, Planet fitness, Downtown Cumberland, Rocky Gap Casino and much more! Explore the vibrant neighborhood or venture out to discover the hidden gems of Cumberland. Book your stay at “The Hidden Tree” today and make unforgettable memories.

FamilyValueTV

4.92 out of 5 average rating, 103 reviews

Top 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 Bath (Berkeley Springs)

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

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!

ValueLocationHot tub

4.96 out of 5 average rating, 428 reviews