Guesthouse vacation rentals in Maryland

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Top-rated guesthouse rentals in Maryland

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

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Guest favorite
The bedroom features a spacious bed adorned with a patterned blanket and decorative pillows. A circular area rug adds warmth to the space. Surrounding wall art complements the vintage aesthetic, while table lamps provide soft lighting. A rocking chair and another seating option are positioned nearby.
Guesthouse in Ellicott City

Cozy Historic Guest House

Located in the heart of Old Ellicott City! This studio is warm, cozy and decorated with almost all vintage furnishings to pay tribute to the 1800s home. The space offers a well stocked bedroom, full bathroom and kitchenette. Relax on the patio or walk to the many cafes and shops on Main Street. Parking is included. The home is built into a hill so you will need to walk up a series of steps & stoned in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

4.92 out of 5 average rating, 137 reviews
Top guest favorite
The main living area features exposed wooden beams above and a cozy sofa adorned with decorative pillows. A small dining table with chairs is positioned near a window, and a charming side table displays a decorative item. Natural light fills the space, enhancing its inviting atmosphere.
Guesthouse in Glenwood

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

4.95 out of 5 average rating, 214 reviews
Top guest favorite
Guesthouse in Frederick

The Landing in the Woods | 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.

4.96 out of 5 average rating, 110 reviews
Top guest favorite
A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.
Guesthouse in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

4.99 out of 5 average rating, 146 reviews
Top guest favorite
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.

4.97 out of 5 average rating, 870 reviews
Top guest favorite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

4.99 out of 5 average rating, 659 reviews
Superhost
The interior of the cottage features a vaulted wooden ceiling with beams, creating an open atmosphere. A spacious sectional sofa faces a wood-burning stove. The kitchen is equipped with modern appliances, while light streams through large windows draped in sheer curtains.
Guesthouse in National Harbor

Urban Cottage, MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

4.92 out of 5 average rating, 780 reviews
Top guest favorite
A charming stone cottage features a red front door with black shutters framing the windows. A friendly dog stands on the stone path, surrounded by lush greenery. The staircase leading to the studio is visible on the right side, along with decorative elements of the owner's residence.
Guesthouse in Towson

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

4.99 out of 5 average rating, 317 reviews
Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 376 reviews
Top guest favorite
Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

5.0 out of 5 average rating, 228 reviews
Top guest favorite
A red barn-style building is positioned on a lush green lawn, surrounded by trees and residential structures. A porch is visible on the upper level, and a colorful wheel mural decorates the front. A gravel path leads to the entrance.
Guesthouse in Cambridge

The Loft at Sailor's Retreat. Waterfront Apartment

Romantic waterfront loft for couples in a charming barn. Relax in a cozy king bed, enjoy a full bath, and cook in a well-equipped country kitchen. Sip wine or coffee on your private balcony overlooking the water, or explore the creek with kayaks and paddleboards. Share the pool (Apr–Oct), lawn games, and game room with one other unit. Perfect for a peaceful getaway to unwind and reconnect. Designed as an adults-only retreat—no children please.

4.99 out of 5 average rating, 125 reviews
Top guest favorite
A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.
Guesthouse in Bushwood

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. Childlren under the age of 12 and pets are not allowed.

4.94 out of 5 average rating, 188 reviews

Popular amenities for Maryland guesthouse rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly guest house rentals

Top guest favorite
A bright and airy bedroom features a spacious bed with a white quilt and an accent pillow. Natural light filters through two windows, illuminating the wood floor. A small dining table with chairs and a wall-mounted air conditioner add functionality to the cozy space.
Guesthouse in Woodbine

Garden Cottage

4.95 out of 5 average rating, 168 reviews
Top guest favorite
A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.
Guesthouse in Highland

Woodland Retreat

4.98 out of 5 average rating, 314 reviews
Top guest favorite
A welcoming covered porch features two white chairs at the entrance of a pink home. Well-maintained shrubs and seasonal flowers border the porch area, while natural light streams through large windows, enhancing the cheerful exterior surrounded by greenery.
Guesthouse in Galesville

Nautical Charm and Relaxing Waterview!

4.95 out of 5 average rating, 188 reviews
Top guest favorite
The entrance features a vibrant yellow door contrasting with a gray exterior. The door is flanked by two windows with decorative glass. A wooden ramp leads up to the door, providing accessible entry into the rental space.
Guesthouse in Takoma Park

Private, above-ground studio

4.95 out of 5 average rating, 203 reviews
Top guest favorite
A tranquil waterfront setting features a multi-level home surrounded by trees, with a spacious deck visible. Adirondack chairs on the dock face the calm waters, reflecting the structure and greenery. Soft outdoor lighting adds a cozy ambiance, enhancing the serene landscape.
Guesthouse in Lusby

Cozy Lakeside Studio Retreat.

4.97 out of 5 average rating, 239 reviews
Top guest favorite
An inviting living space featuring a spacious L-shaped couch adorned with vibrant throw pillows. A glass dining table is positioned in the foreground, complemented by a bottle of rosé and two glasses. A modern kitchen with stainless steel appliances and bar seating can be seen in the background.
Guesthouse in Rockville

Modern Farmhouse Apartment. Close to Metro

4.94 out of 5 average rating, 238 reviews
Guest favorite
The image illustrates a charming tiny home nestled among trees, featuring a spacious bluestone patio with outdoor seating and a fire pit. In the background, a gas grill is positioned nearby. Lush green grass surrounds the area, creating a serene and inviting setting.
Guesthouse in Annapolis

Lil’ House - A Serene Tiny Home Experience

4.95 out of 5 average rating, 214 reviews
Guest favorite
The exterior of the remodeled guest cottage is shown, featuring a brick façade with two symmetrical entries. Each entry is framed by white columns and topped with a maroon awning. Large windows with white trim offer views into the interior, while a gravel parking area is visible in the foreground.
Guesthouse in Annapolis

Private Cottage on gated estate

4.93 out of 5 average rating, 134 reviews

Guest house rentals with a patio

Guest favorite
The spacious interior features a high, wooden ceiling with large windows allowing natural light to illuminate the room. A cozy seating area with a patterned chair complements a bed with a white duvet. Sliding glass doors offer access to an exterior deck.
Guesthouse in Rock Hall

Carriage House

4.89 out of 5 average rating, 112 reviews
Top guest favorite
A comfortable living area features a spacious sectional sofa with decorative pillows, paired with two accent chairs. Light-colored walls and carpeting create a neutral backdrop, while a television rests on a wooden stand opposite the seating. Natural light is offered through nearby windows.
Guesthouse in Pocomoke City

2 Bedroom Apartment

4.94 out of 5 average rating, 193 reviews
Top guest favorite
The exterior features a clean facade with light-colored siding and a white door, complemented by a window with dark shutters. A small garden area is present beneath the window, accentuated by green plants and decorative elements. The well-maintained lawn adds to the overall appeal.
Guesthouse in Edgewater

1 large room efficiency in detached garage.

4.99 out of 5 average rating, 179 reviews
Top guest favorite
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

The Loft Guest House w/wifi workspace, gym etc

4.95 out of 5 average rating, 192 reviews
Guest favorite
Guesthouse in Elk Mills

Private Country Guesthouse Getaway Minutes from UD

4.97 out of 5 average rating, 176 reviews
Top guest favorite
A bright studio apartment features a queen-size bed dressed in soft gray linens. A compact sofa is positioned nearby. A ceiling fan and wall-mounted TV enhance the modern space, with a kitchenette and private entrance visible in the background.
Guesthouse in Ocean Pines

Studio Apartment above Garage

5.0 out of 5 average rating, 115 reviews
Top guest favorite
Guesthouse in Frederick

Luxury Cozy Guesthouse w/ Private Entry & Garage

4.97 out of 5 average rating, 36 reviews
Guest favorite
A two-story apartment building is depicted with a light gray exterior and dark shutters. Outdoor steps lead to the upper entrance. A spacious driveway is visible in front of the garage doors, surrounded by green grass and trees in the background.
Guesthouse in Laurel

Cozy & Quiet 2 Bed Rm ADU Apart near DC&Baltimore

4.91 out of 5 average rating, 70 reviews

Guest house rentals with a washer and dryer

Top guest favorite
Guesthouse in Keymar

Historic country guesthouse, newly renovated.

4.99 out of 5 average rating, 102 reviews
Guest favorite
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

4.93 out of 5 average rating, 109 reviews
Top guest favorite
An open floor plan showcases a spacious living area with two gray sofas and a brown chair placed on a dark area rug. A kitchenette is visible in the background, complemented by bar stools. Natural light enters through multiple windows, illuminating the space.
Guesthouse in Baltimore

Woodberry Studio Retreat

4.89 out of 5 average rating, 271 reviews
Guest favorite
The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.
Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

4.9 out of 5 average rating, 371 reviews
Guest favorite
A single-story home is positioned at the end of a paved driveway, surrounded by greenery. The exterior features a brown roof, light-colored siding, and multiple windows. A white bench is located in front of the house, offering a place to relax in the garden-like setting.
Guesthouse in Cape St. Claire

"L'auberge du Cape Saint Claire"

4.84 out of 5 average rating, 235 reviews
Top guest favorite
The exterior of a charming carriage house apartment is presented, featuring a well-maintained garden, stone pathway, and illuminated by string lights. Two adirondack chairs and a fire pit enhance the inviting outdoor space, with lush grass and mature trees providing a natural backdrop.
Guesthouse in Annapolis

Carriage House near Navy Stadium, parking, pets

4.95 out of 5 average rating, 119 reviews
Guest favorite
The guesthouse exterior presents a gray facade with a welcoming porch. Lush greenery, including manicured bushes and large trees, frames the entrance. A paved walkway leads to the door, surrounded by planters. The house stands under a clear blue sky, providing a serene setting.
Guesthouse in Middletown

Indulge, Fresh Flowers, Frederick County Haven

4.93 out of 5 average rating, 336 reviews
Superhost
The exterior of the carriage house is shown, featuring light-colored wooden siding, large windows, and a welcoming entrance. Surrounding the building is a landscaped area with brick pathways and greenery, creating a pleasant outdoor space.
Guesthouse in Chestertown

Cozy Carriage House

4.86 out of 5 average rating, 198 reviews

Destinations to explore