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Guesthouse vacation rentals in Maryland

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Maryland

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

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The living area features a cozy sofa adorned with colorful pillows, complemented by a sleek coffee table. Natural light enters through large windows, while a spiral staircase leads to the loft. An inviting front door opens to the outdoor space, enhancing the overall ambiance.

Guesthouse in Rockville

4.87 out of 5 average rating, 212 reviews

Adorable private 1-bedroom place, close to metro

Adorable 1-bed guesthouse close to metro station.Features a cozy double bed, a pull-out sofa and chic kitchenette.Private outdoor space with comfy chairs and fire pit.Street parking available on adjacent street.We are a long walk, or a short bus ride (15 minute walk) to the WhiteFlint metro station. 0.8 miles to Pike&Rose with lots of restaurants and shopping malls.Experience D.C. and return to your private cozy home away from home! 10 min walk to the winding creek park with trails by the creek!

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

4.9 out of 5 average rating, 301 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

The pool area features a crystal-clear pool bordered by stone pavers and landscaped greenery. A pool house with large glass doors is visible in the background, accompanied by a defined hot tub and neatly arranged lounge chairs. Surrounding trees and bushes enhance the outdoor setting.

Guesthouse in Monrovia

4.96 out of 5 average rating, 157 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:)

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

4.97 out of 5 average rating, 765 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 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

4.98 out of 5 average rating, 295 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool (weather permitting) and adjacent walking trails.

The bedroom features a plush queen bed dressed in neutral linens, complemented by two bedside lamps and coastal-themed artwork. A cozy sitting area includes a light blue armchair and a small table. Ample storage is provided by a closet with sliding doors.

Guesthouse in Annapolis

4.86 out of 5 average rating, 102 reviews

Cozy Retreat w/Private Beach Access

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

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

4.99 out of 5 average rating, 614 reviews

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.

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 Fort Washington

4.93 out of 5 average rating, 744 reviews

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.

Top guest favorite

A private deck is presented with woven seating arrangements, including a unique hanging chair and a sofa. A round table is placed at the center, surrounded by natural greenery. The wooden flooring and patterned rug enhance the outdoor relaxation space.

Guesthouse in Elk Mills

4.98 out of 5 average rating, 137 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

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

4.99 out of 5 average rating, 257 reviews

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.

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

4.99 out of 5 average rating, 297 reviews

Waterfront Getaway - 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.

Top guest favorite

An outdoor seating area features two vibrant red chairs placed on a mulch bed. A small table stands between the chairs, surrounded by greenery and decorative plants. A bright red door provides an inviting entrance, while a vintage wrought iron fence encloses the area for privacy.

Guesthouse in Catonsville

4.97 out of 5 average rating, 286 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. It is not appropriate for people who cannot climb a ladder. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

Vacation rentals for every style

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Luxurious estates for the ultimate escape

Popular amenities for Maryland guesthouse rentals

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Top guest favorite

A spacious studio displays warm wooden flooring complemented by an area rug. A queen bed is positioned along the wall, while a kitchenette is situated in the corner. A small dining table and two chairs are present, and a desk with a lamp provides a work area.

Guesthouse in Potomac

4.88 out of 5 average rating, 51 reviews

Potomac Sanctuary

A cozy living space is highlighted by a brick fireplace, with a television mounted above. A queen bed is positioned near a large window covered by light curtains. A wooden coffee table sits in front of a full sofa bed, complemented by a small potted plant.

Guesthouse in Germantown

4.97 out of 5 average rating, 36 reviews

Cozy Studio with fireplace. Free Tesla charging.

A well-lit bedroom features a spacious bed adorned with a floral quilt. Soft lighting is provided by sconces above the headboard, and a floral wall decoration adds a touch of charm. A window with a white frame offers natural light, complemented by a nearby door.

Guesthouse in Beltsville

5 out of 5 average rating, 10 reviews

Guest studio with kitchenette - Private Entrance

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

4.94 out of 5 average rating, 179 reviews

Nautical Charm and relaxing waterview!

Top guest favorite

A serene garden landscape is visible, showcasing a pond surrounded by smooth stones and lush green plants. A flag stands tall nearby, and a meandering path leads through the manicured yard, featuring various plant beds and a wooded backdrop.

Guesthouse in Cambridge

4.98 out of 5 average rating, 63 reviews

Camelot Cottage

The living room features a mix of seating options, including a pink sofa and a cozy armchair. Large windows allow natural light to fill the space. A television is mounted on a black stand, and a patterned area rug lies on the hardwood floor, creating a welcoming environment.

Guesthouse in Baltimore

4.84 out of 5 average rating, 212 reviews

Cottage in beautiful Mount Washington

Top guest favorite

A vibrant sunset casts a warm glow over the water, blending hues of orange, purple, and pink. Silhouetted pilings rise from the bay, while gentle waves reflect the colorful sky. A small dock is visible in the foreground, inviting guests to enjoy the serene view.

Guesthouse in Deal Island Historic District

5 out of 5 average rating, 39 reviews

Blue Crab Bungalow

A set of double glass doors with multiple panes is visible, providing a view of the staircase leading to the private entrance. Light filters through sheer curtains, creating a soft ambiance around the entryway.

Guesthouse in Upper Marlboro

4.87 out of 5 average rating, 89 reviews

Near Six Flags America

Guest house rentals with a patio

A cozy living space features a brown reclining sofa paired with a black accent chair. A wooden coffee table centers the room, and a large art print is mounted on the wall. A full kitchen showcases modern appliances and ample counter space, illuminated by overhead lighting.

Guesthouse in Cambridge

5 out of 5 average rating, 5 reviews

Cozy Guest House Near Park

A modern guest house is depicted, showcasing light gray siding and a two-car garage below. A small tree sits in the foreground, while a balcony with black railings is visible on the upper level. Lush green grass surrounds the property.

Guesthouse in Hyattsville

4.92 out of 5 average rating, 49 reviews

New Private Guest House in Historic Area & Near DC

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, 171 reviews

“The Loft” Guest House w/wifi workspace, gym etc

An open living area features a comfortable seating arrangement with a light-colored sofa and a coffee table atop a soft rug. The kitchen is visible in the background, defined by wooden cabinetry and modern appliances, with natural light illuminating the space.

Guesthouse in Mount Airy

4.95 out of 5 average rating, 131 reviews

Treasured Hideaway on the Hill

The entrance pathway leads to a sliding glass door framed by large windows. Seasonal string lights are delicately strung along the railing. Surrounding foliage is vibrant with fall colors, enhancing the natural setting among the trees.

Guesthouse in Reisterstown

5 out of 5 average rating, 6 reviews

Spacious Forested Oasis

Top guest favorite

A bright studio guesthouse features vaulted ceilings and hardwood flooring. Natural light fills the space through multiple windows. A cozy sofa is positioned near a side table, while a spacious bed is located against the opposite wall, accented by a blue dresser.

Guesthouse in Towson

4.98 out of 5 average rating, 170 reviews

Sunny Guesthouse steps from Towson!

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

4.98 out of 5 average rating, 123 reviews

1 large room efficiency in detached garage.

Top guest favorite

A spacious king-size bed is framed by natural wood, complemented by matching nightstands with lamps on either side. Soft pillows adorn the bed, and a decorative piece hangs on the wall nearby, enhancing the serene atmosphere in the room.

Guesthouse in Brandywine

5 out of 5 average rating, 47 reviews

Quiet cottage in the woods. King-bed suite.

Guest house rentals with a washer and dryer

A modern kitchen area is displayed, featuring light cabinetry and sleek stainless-steel appliances. A dining table with two stools is positioned in front of the kitchen, complemented by a potted plant. Natural light illuminates the open space, highlighting the wood flooring and inviting design.

Guesthouse in Annapolis

4.88 out of 5 average rating, 200 reviews

Annapolis Guesthouse - Completely Separate Space

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

4.88 out of 5 average rating, 229 reviews

Woodberry Studio Retreat

Top guest favorite

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, 134 reviews

Yoder School Guest House with wifi and hot tub

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

4.97 out of 5 average rating, 200 reviews

Cozy Lakeside Studio Retreat.

Top guest favorite

A spacious backyard features a hammock strung between two trees and a stone fire pit surrounded by seating. Nearby, a propane grill and a stack of firewood are arranged on a grassy lawn, offering a relaxed outdoor setting.

Guesthouse in Annapolis

4.99 out of 5 average rating, 143 reviews

Garden View, a spacious 1 bedroom with loft.

Top guest favorite

A spacious living area features plush seating in elegant patterns, arranged around a round coffee table. Decorative lamps provide soft lighting, while rich red wallpaper and floral accents contribute to a warm atmosphere. A flat-screen TV is mounted on the wall, complemented by tasteful decor.

Guesthouse in Frederick

4.98 out of 5 average rating, 190 reviews

Romantic Getaway! Heated Spa - Open Year Round!

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

4.99 out of 5 average rating, 126 reviews

Rosses Chance Guest House

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

4.95 out of 5 average rating, 189 reviews

The Caretaker's Cottage-Historic Roundabout Hills

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