Guesthouse vacation rentals in Frederick County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Frederick County

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

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Guest favorite

Guesthouse in New Windsor

5 out of 5 average rating, 13 reviews

Guesthouse at Toccoa Homestead

Experience peacefulness and beauty of Frederick County countryside, close to Frederick, Westminster and Mount Airy. The guesthouse is in Historic Agricultural Preservation land on a ridge. Enjoy morning sunrise with coffee on the landing or spectacular sunsets over Catoctin Mountains with horses in the foreground at the end of the day. Nearby wineries and breweries are close to this peaceful property surrounded by rolling hillsides. Keep it simple at this peaceful and centrally-located place.

Guest favorite

Guesthouse in Middletown

5 out of 5 average rating, 110 reviews

Cottage, Pool, & Breakfast on 100ac Horse Estate

Enjoy the unique opportunity to spend time on a stunning Maryland horse farm and estate with private access to the Appalachian Trail in Maryland's Blue Ridge mountains. Located in historic Middletown, the farm is just 60 miles from downtown DC and 20 minutes west of Frederick. Our lovingly renovated 1900 guest cottage sits above an active mountain spring and beside the estate's main residence. You'll encounter chickens, cattle, horses and abundant wildlife as you hike and explore the property.

Guest favorite

Guesthouse in Middletown

4.95 out of 5 average rating, 268 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

Guest favorite

Guesthouse in Lovettsville

4.93 out of 5 average rating, 15 reviews

The Tuberose Suite

Nestled on 16 acres, right on the outskirts of the historic german town of Lovettsville, you will find yourself within a 20 minute radius of some of the best restaurants, wineries, and breweries, in Loudoun County, along with plenty of activities like hiking, biking, and kayaking. After a day of exploring, come home to relax by the firepit, grill in the outdoor kitchen or unwind with a steam shower. Enjoy stargazing and the beautiful views of the Short Hill Mountians right from the backyard.

Guest favorite

Guesthouse in Lovettsville

4.93 out of 5 average rating, 160 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 & convertible sofa downstairs (full). The cabin is next door to our house & shares a fence with our pasture where our miniature donkeys live. We have yappy dogs and friendly outdoor cats. we're in the country, so bugs do make their appearance, but they tend to go straight to the window sills.

Guest favorite

Guesthouse in Monrovia

4.97 out of 5 average rating, 143 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

Guest favorite

Guesthouse in Myersville

4.93 out of 5 average rating, 224 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 favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 696 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota 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.

Guest favorite

Guesthouse in Frederick

4.97 out of 5 average rating, 36 reviews

Boutique space at Marble Ridge

Boutique accommodations are defined as a unique and luxurious space~and that is what you will find here at Marble Ridge. The private entrance opens up to a living space that is comfortably modern with clean lines. The large picture windows allow tons of natural light and a spectacular view. You will have all the amenities available to you such as a full kitchen with refrigerator/freezer, stove/oven, microwave, coffee maker, dishwasher, WiFi, TV, fireplace, private full bath.

Guest favorite

Guesthouse in Frederick

4.97 out of 5 average rating, 327 reviews

The Shady Bear Cabin

After a complete renovation, we decided the cabin would be perfect for Airbnb. It's completely separate from the main house and offers both of us a great deal of privacy. It is also warm and cozy yet extremely comfortable. Please be aware that we have dogs on the property. If you are not comfortable with dogs, please do not book this cabin. If you are, we hope to see you. DURING THE PANDEMIC WE WILL BE FOLLOWING AIRBNB'S ENHANCED CLEANING PROTOCOL.

Guest favorite

Guesthouse in Keymar

4.98 out of 5 average rating, 55 reviews

Historic country guesthouse, newly renovated.

Birthplace of the Star Spangled Banner, Keymar, MD is home to Francis Scott Key. This original General Store (now our Guesthouse), on old Key property that was built in the late 1800s, has been impeccably remodeled to allow you every comfort while being centrally located to historic Gettysburg, PA, Frederick, MD, the beautiful Catoctin Mountains, Mount Saint Mary’s University, Liberty Mountain Ski Resort, and so much more. Settle into history.

Guest favorite

Guesthouse in Lovettsville

4.99 out of 5 average rating, 119 reviews

Modern dreamy mountain view oasis in wine country

Right in the heart of Loudoun County's wine, beer and equestrian country. If you are looking for an outdoor getaway with access to the Ap Trail, biking, kayaking, etc., here for the wine and beer or simply for a change of scenery, this is the place for you. Watch the sun go down right from your bed or, "The Meadow" with the Blue Ridge Mountains as your backdrop. Slowly sip coffee or tea from the hammock, it's up to you. Book now!