Holiday rentals with outdoor seating in Pikesville

4.98 out of 5 average rating, 221 reviews

Guest suite in Woodstock

Our Retreat -in a peaceful setting.

Private- apartment in the lower level of our house. House in a rural setting- you may spot white tail deer or other wildlife.Enjoy the peaceful tranquil setting.We are within 5 minutes by car to Rte 70 and shopping centers. Our space isn't childproof. Workout equipment available for use at your own risk. We control the HVAC and will adjust as requested. May not be suitable for those with mobility issues due to the walk to the entrance. Non smoking. We aren't set up for heavy cooking. No stove.

LocationValueHeating

4.94 out of 5 average rating, 114 reviews

Home in Owings Mills

Dog-Friendly Home | Bedroom on primary + Full AC

Enjoy easy summer stays at Grandma’s House in Owings Mills, a cozy dog-friendly retreat with full AC, fast Wi-Fi, laundry, driveway parking, fully stocked kitchen, and fenced side yard. This nostalgic home sits on a peaceful 1/2-acre lot with mature trees and frequent deer sightings. Perfect for sports families, medical travel, local events, and multi-generational visits with a primary bedroom on first floor + a private upstairs. Wegmans nearby; about 30 mins to Baltimore. Permit: RHR-2026-00248

LocationOutdoor spacesHiking

4.95 out of 5 average rating, 299 reviews

An open living space features high ceilings with exposed beams and a neutral color palette. A comfortable sectional sofa, two accent chairs, and a coffee table are arranged over a decorative area rug. Natural light filters through the large windows, highlighting a media console and decorative baskets.

Home in Timonium

* Gorgeous House w/ Luxury, Charm, & Comfort *

Imagine having your entire family or friends together all under the same roof enjoying a beautifully decorated, renovated house with loads of amenities. Well, imagine no more!!!! This home has it all – 4 beds (3 king / 1 queen) with plush mattresses & high end bedding & 2 baths, 3 smart TVs, washer/dryer closet, open living space w/ 20 ft ceilings leading to farmhouse style kitchen full of functionality & style, and awesome deck w/ sectional couch, mounted TV, montrous picnic table, & 2 heaters.

LocationOutdoor spacesHospitality

Guesthouse in Ellicott City

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.

4.93 out of 5 average rating, 113 reviews

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.

ValueLocationDecor

4.94 out of 5 average rating, 158 reviews

A living area features a light grey sofa facing a large window that invites natural light. Two woven chairs are positioned nearby, and a stone fireplace adds a touch of warmth to the space. Modern light fixtures are installed on the walls.

Home in Catonsville

Tudor Home

Enjoy your stay in this cozy, newly remodeled Tudor home in a historic and architecturally eclectic neighborhood in Catonsville, MD! You’ll be close to everything but far enough to enjoy a relaxing trip. The home features Four bedrooms, two full baths, a fully stocked kitchen, a full basement, and 18ft ceilings on the main level. You will enjoy 65, 42, and 32-inch smart TV's throughout the home. In addition, a private upstairs main suite with King size bed, sofa seating area, and workstation.

Outdoor spacesLocationWalkability

4.97 out of 5 average rating, 181 reviews

The exterior of a cozy blue and gray two-story house features red shutters and a welcoming front porch. A private driveway accommodates a vehicle beside a manicured garden bed with flowers. The entrance is framed by steps leading to a white railing, inviting guests inside.

Home in Hampden

Full house in “coolest neighborhood in America”

Small but cozy single family in Northern Baltimore, located in the very sought after Hampden neighborhood. 5 minute walk to “the Avenue” and 34th Street lights at Xmas. Directly across the street is a Walgreen’s, MOM’s Organic Market, gym, restaurants, UPS Store, etc. A private driveway, manicured back yard w/ hardscape, fire pit and tons of indoor amenities offer a convenient and relaxing stay in this quaint Baltimore hood. Cleaned by COVID-trained professionals after each reservation.

ValueLocationParking

Guest suite in Catonsville

A classic brick Colonial house is surrounded by well-maintained gardens and lush greenery. Large trees provide shade over the front lawn, which features manicured bushes and young saplings, contributing to the inviting exterior of the home.

4.94 out of 5 average rating, 570 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

LocationOutdoor spacesBreakfast

Guest suite in Randallstown

An open layout is showcased with a spacious living area, featuring a comfortable sectional sofa and a coffee table. A smart TV is positioned on a stand, while a dining set is visible in the background. Natural light filters through the windows, illuminating the space.

4.99 out of 5 average rating, 147 reviews

Private Efficiency Suite ~ King Bed ~ Baltimore Co

Welcome to Hickory Roots Hideaway! A cozy yet spacious 750 sq ft efficiency guest suite situated on our picturesque 4 acre homestead! Great Wi-Fi and amenities make this a perfect getaway even if work and virtual school must continue. Enjoy a relaxing stay - you are welcome to explore our garden, shoot some hoops in our basketball court, or get to know our adorable farm animals! We are conveniently located with easy access to I-70, I-795, and just 30 minutes from downtown Baltimore!

LocationOutdoor spacesWalkability

4.99 out of 5 average rating, 306 reviews

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.

LocationOutdoor spacesCleanliness

4.93 out of 5 average rating, 122 reviews

Home in Monkton

Cozy up in the restored 1820s Miller's House!

The Miller's House is a quaint and beautiful, newly restored two-bedroom house that sits on a small river and is also a national historic landmark. The house has been painstakingly restored recently, with modern amenities you'd expect such as all-new appliances and high speed WiFi. Proximity to the Gunpowder Falls for fishing or tubing, the NCR trail (less than .2 mile away) and endless roads to bike on make it a great escape.

ValueOutdoor spacesHiking

Farm stay in Cockeysville

A spacious master suite features a king-size bed with a decorative canopy, flanked by nightstands. Two armchairs provide seating, and a woven area rug adds warmth. A mural depicting nature adorns the wall, while large windows allow natural light. An accessible doorway leads to the bathroom.

4.95 out of 5 average rating, 135 reviews

Master's Suite · 1920s Tudor Estate, Hunt Valley

A king-size suite in the gatehouse of a 1920s English Tudor estate, deep in Maryland’s horse country — peaceful and private, but an easy drive from the city. • King bed, vaulted ceilings, hand-painted mural • Carrara marble bath with a clawfoot soaking tub • Private sun porch over open farmland • Pool, tennis & miles of farmland to wander • Hunt Valley 10 min · Towson 15 · Baltimore 25 · Ellicott City/Columbia ~35

Outdoor spacesLocationComfort

4.82 out of 5 average rating, 145 reviews

A two-story home built into the hillside is framed by lush greenery. A wooden porch, supported by stone pillars, features a railing and an American flag. The exterior showcases a mix of siding and stone, with large front windows allowing natural light into the interior.

Home in Ellicott City

Mello-Ray River House

PETS STAY FREE!! At our Historic 3BR, 2BA colonial on Frederick Rd—once the main route from Baltimore to Ellicott City. Built on a foundation dating to the late 1700s, the current structure has stood since 1875. Overlooks the Patapsco River and the B&O Railroad, the first in the nation. Features hardwood floors, modern kitchen, central air, and fenced patio. Walk to shops, parks, and the historic district.

Outdoor spacesValueCondition

Popular amenities for Pikesville outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.98 out of 5 average rating, 109 reviews

A modern kitchen features dark wood cabinetry and light-colored countertops. Stainless steel appliances, including a stove and microwave, are visible. An island with two high chairs is illuminated by a stylish light fixture, while sliding glass doors provide access to the outdoor area.

Home in Joppatowne

Two bedroom small ranch with beautiful forest view

Outdoor spacesLocationSleep quality

4.94 out of 5 average rating, 115 reviews

An inviting family room features a pool table at its center, surrounded by comfortable seating and dining areas. Natural light illuminates the space through large doors leading to the deck. Ceiling fans and a warm color palette contribute to the open, relaxed atmosphere.

Home in Columbia

Rancher by Wash/Balt/Annap w/pool table, Kit, Deck

Outdoor spacesLocationBackyard

4.93 out of 5 average rating, 123 reviews

A cozy living area is furnished with two floral-patterned sofas, complemented by colorful throw pillows. A round coffee table sits at the center, topped with decorative items. Natural light filters in through sheer curtains, enhancing the warm ambiance of the space.

Home in Mount Vernon

Peggy's Place - Historic Rowhome in the City

LocationOutdoor spacesPets

4.94 out of 5 average rating, 315 reviews

A spacious rooftop deck features a shaded seating area surrounded by greenery. Comfortable couches provide ample seating, and a glass table holds decorative items and refreshments. The backdrop showcases colorful buildings and autumn foliage.

Home in Canton

Luxury Home, Gorgeous Roof Deck (By Marina & Park)

LocationValueLaundry

4.95 out of 5 average rating, 191 reviews

A cozy living area features a gray sectional sofa with a yellow throw draped over it. Wood accents and a patterned area rug complement the warm hardwood floors. An adjacent dining space is visible, showcasing a rustic brick wall and a dining table with elegant lighting.

Home in Fells Point

Charming 4 bedroom home just steps to the water!

ValueOutdoor spacesAmenities

4.98 out of 5 average rating, 120 reviews

A large flat-screen television is mounted on a brick wall above a stone fireplace. The screen displays a colorful scene of hot air balloons against a blue sky. Surrounding the fireplace are potted plants and shelves filled with DVDs, adding to the cozy atmosphere.

Home in Glen Burnie

Glen Burnie Escape

LocationValueAccuracy

Superhost

A bright living room is showcased with a large wall-mounted TV and a minimalist coffee table. Green plants are placed in front of a brick accent wall, while light from the entrance highlights the warm wooden flooring. Comfortable seating is arranged to create an inviting space.

Home in Baltimore

4.91 out of 5 average rating, 129 reviews

Camden Luxury Art house • Stadium/Topgolf Walkable

Outdoor spacesLocationAmenities

Superhost

A single-story house features a welcoming entrance with a front door framed by simple step railings. A spacious driveway leads to the home, and a newly fenced backyard is visible to the left, surrounded by well-maintained grass and brick pathways.

Home in Catonsville

4.85 out of 5 average rating, 157 reviews

Delightful 4-Bed Whole House with Easy Parking

Outdoor spacesLocationTV

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 120 reviews

A well-maintained brick exterior of a home is shown, featuring a front pathway leading to a covered entrance. Lush greenery surrounds the property, and seasonal leaves are scattered across the lawn. A white fence can be seen partially in the background, enhancing the outdoor space.

Apartment in Bel Air

Small town getaway- Bel Air

LocationValueCondition

Apartment in Mount Vernon

A bedroom features a queen-sized bed with a light blue quilt and neutral linens. Two decorative pendant lights hang above nightstands on either side. A colorful wall art piece provides a playful touch. Warm wooden flooring complements the room's design.

4.97 out of 5 average rating, 205 reviews

Mid-Century Vibe in Mount Vernon.

LocationValueShared spaces

Apartment in Sparrows Point

A spacious living area features a large sectional sofa arranged around a central area rug. The open layout includes a kitchen with modern appliances visible in the background. Ambient lighting and ceiling fans enhance the room's comfort and functionality.

4.97 out of 5 average rating, 105 reviews

Safe, quiet neighborhood close to downtown!

Outdoor spacesLocationView

Apartment in Northeast Washington

A spacious living area is highlighted by large angled windows, allowing natural light to fill the space. A comfortable sectional sofa is complemented by a coffee table, while a kitchenette is visible in the background. An attached image shows a private outdoor deck with seating.

4.98 out of 5 average rating, 296 reviews

Luxury escape in DC now with a private Deck!

LocationValueIndoor spaces

4.88 out of 5 average rating, 120 reviews

A cozy living area features a navy blue sofa adorned with decorative pillows and a soft throw blanket. A round coffee table with an artistic design sits in front of the sofa, complemented by a tall indoor plant and colorful tulips on the windowsill.

Apartment in Baltimore

Gorgeous Garden Apt. in Historic Reservoir Hill

LocationOutdoor spacesParking

4.97 out of 5 average rating, 350 reviews

A spacious gathering area is highlighted by a comfortable sofa and a light armchair, complemented by a brown coffee table. Wall art and mirrors add character to the gray walls. Soft rugs cover the wood-like flooring, creating a cozy atmosphere for relaxation.

Apartment in Sykesville

Heart of Sykesville! 2 Bedroom Suite! Walk to town

Outdoor spacesValueCondition

4.97 out of 5 average rating, 306 reviews

A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.

Apartment in Essex

A place unique on sue creek

ValueOutdoor spacesCheckout

4.85 out of 5 average rating, 164 reviews

A two-story home is shown with a light brown exterior and green shutters. A front porch features a railing and seasonal decorations. Stone steps lead to the entrance, surrounded by well-maintained grass and a neatly trimmed evergreen shrub.

Apartment in Nottingham

Bright and Cozy 2nd floor apt

ValueLocationHeating

Condo rentals with outdoor seating

Condo in Northwest Washington

A multi-story brick building is featured, showcasing a welcoming entrance with a covered porch. Potted plants adorn the steps, while green grass and shrubs provide a soft landscaping touch. Nearby structures are visible, highlighting a mix of architectural styles.

4.86 out of 5 average rating, 110 reviews

Lovely 1BR condo in quiet neighborhood

LocationOutdoor spacesHeating

A bright living room features large windows dressed with light curtains, allowing natural light to fill the space. A comfortable sofa and armchair are arranged around a sleek coffee table, with shelves displaying books and decorative items, contributing to a welcoming atmosphere.

4.98 out of 5 average rating, 165 reviews

New Downtown Annapolis Condo With Free Parking

LocationOutdoor spacesCheckout

Condo in Columbia Heights

A three-story, brick-front townhouse is depicted with a welcoming front porch and stairway leading to the entrance. Surrounding greenery enhances the neighborhood's charm, while the contrasting colors of nearby homes create a vibrant streetscape.

4.9 out of 5 average rating, 118 reviews

Modern Condo, 2 Bed/2 Bath, Rooftop - 6 PPL

ValueOutdoor spacesHospitality

A spacious living area is presented with a blue reclining sofa facing a large wall-mounted television. Warm wood cabinetry complements the kitchen area in the background, illuminated by soft lighting. A cozy electric fireplace adds warmth, creating an inviting space for relaxation.

4.84 out of 5 average rating, 101 reviews

Anchors Away

ValueOutdoor spacesLayout

4.97 out of 5 average rating, 142 reviews

A scenic view is captured from the balcony, showcasing a blend of rooftops and greenery with a gentle road winding through the neighborhood. The sunset casts a warm hue, illuminating the buildings and trees, providing a serene atmosphere.

Condo in Chevy Chase

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

ValueLocationView

4.98 out of 5 average rating, 115 reviews

Captains Quarters | Waterfront & Pool

LocationOutdoor spacesShared spaces

Condo in Northwest Washington

A cozy living area is highlighted by a large 65" TV on a white media console, flanked by tall speakers. A soft sofa is paired with a round dining table set for two, complemented by a potted plant and framed artwork on the wall.

4.9 out of 5 average rating, 270 reviews

New, Sunny, 2BR - Parking, Patio, Firepit

Outdoor spacesLocationParks

A welcoming living area features a light-colored sofa and an upholstered armchair, positioned around a central wooden coffee table. A unique area rug with intricate patterns adds warmth. The kitchen area, visible in the background, is equipped with modern appliances and a breakfast bar with stools.