Holiday rentals with a patio in Annapolis

The exterior of a charming historic building features a welcoming front porch adorned with seating. Lush green trees and blooming flowers enhance the inviting atmosphere. American flags are displayed, highlighting the traditional character of the neighborhood.

4.99 out of 5 average rating, 136 reviews

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

4.96 out of 5 average rating, 181 reviews

The exterior of a historic townhome is showcased, featuring red brick walls and black shutters. Lush greenery and colorful flowers enhance the garden area. A flag may be seen hanging from the building, set against a clear blue sky.

Townhouse in Annapolis

Historic 3 Bedroom Downtown Annapolis Townhome

Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

5 out of 5 average rating, 107 reviews

A spacious living area, featuring a small sectional couch facing a TV mounted on the wall. A foosball table occupies the foreground, while a dining nook with a round table and chairs is visible in the background. Soft artificial lighting enhances the relaxed setting.

Home in Crownsville

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

4.96 out of 5 average rating, 112 reviews

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.

Condo in Annapolis

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen, BR2 with Full. LR w/sofa

Superhost

A relaxing hot tub is positioned surrounded by lush greenery and soft grass. Two wine glasses and a bottle are placed on a wooden tray, suggesting a tranquil atmosphere. The bubbling water is gently steaming under a clear blue sky.

4.9 out of 5 average rating, 162 reviews

The Naval Nook 1.3 mi. from Downtown Annapolis

Welcome to your home away from home at the Naval Nook! ~ 4 min. Uber from Downtown Annapolis ~ Brand New Hot Tub ~ Cool Electric AC ~ King Bed ~ Sunroom with Daybed and Trundle ~ Zero Gravity Chairs ~ Outdoor Dining table ~ Beautiful Spacious & Comfortable bedrooms ~ Couch w/ Queen Bed pullout ~ 4 Smart TVs in each bedroom & living room ~ Tiled showers w/ shampoo & conditioner ~ Fully equipped kitchen ~ Luxurious Linens ~ Luxury Electric Fireplace Airbnb Registration #: STR23-145225

4.93 out of 5 average rating, 110 reviews

A charming exterior is displayed, featuring a white wooden facade and a welcoming entrance. A brick pathway leads to the door, which is illuminated by a warm light fixture. Decorative greenery frames the doorway, enhancing the home's inviting character.

Apartment in Annapolis

Historic Annapolis Rental Minutes from Downtown

Immerse yourself in all Annapolis has to offer in this newly restored historic home. This charming rental neighbors the Naval Academy and is just a 5 minute walk to the heart of downtown Annapolis. This home has 2 bedroom and 1 full bath. This is the perfect place to stay whether you're looking to explore historic Annapolis, the Naval Academy grounds, or even taking a day trip to Washington D.C. Inside the home you'll find cozy furniture, new finishing's, and wifi throughout the house.

4.98 out of 5 average rating, 129 reviews

A Bullfrog hot tub is situated under a wooden gazebo, with water glistening in sunlight. A plush robe is draped over the edge alongside a straw hat and a rolled towel. A grassy area and wooden privacy fence complete the serene outdoor setting.

Home in Cape St. Claire

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

4.94 out of 5 average rating, 198 reviews

Guest suite in Arnold

Cozy 1-Bedroom Retreat Near Annapolis, Sleeps 4

*New hot tub and pergola installed!* 💗 This updated suite is designed for comfort & convenience. Enjoy a king bed and a LoveSac sofa that converts into a queen bed, perfect for 2-4 guests. The suite includes a private en-suite bathroom, high-speed internet, a fully furnished kitchen, and a coffee bar to make you feel right at home. Located just 4 miles from Annapolis, you're close to all the best spots. Whether you’re here to relax or explore, this suite has everything you need!

4.92 out of 5 average rating, 115 reviews

The entrance features a welcoming front door adorned with a decorative wreath, flanked by windows with shutters. A small stairway leads up to the door, with a concrete path that is surrounded by greenery.

Apartment in Annapolis

King George Hideaway

Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car and walk everywhere! Lots of shopping, restaurants, tours, cruises & nightlife. The unit is located on the 3rd floor. My place is perfect for couples, solo and business travelers. There is a large living room space with a full pull out couch, tv and dining table. The bedroom has a queen bed with a tv. There is a small full kitchen and updated bathroom.

The front exterior of the home features vibrant, blooming flowerbeds with a variety of blue and pink flowers. Two hanging planters with yellow flowers adorn the entryway, while a charming red door stands out against the yellow walls. A small seating area with dark chairs is visible on the porch.

5 out of 5 average rating, 185 reviews

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

4.95 out of 5 average rating, 131 reviews

A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.

Condo in Annapolis

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Place to stay in Glen Burnie

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

4.93 out of 5 average rating, 384 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Popular amenities for Annapolis Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

Apartment in Upper Marlboro

4.94 out of 5 average rating, 191 reviews

Kone Oasis- hot tub, pool, theater/game rm.

Apartment in Capitol Hill

A cozy living area features a dark grey sofa with a decorative pillow, accompanied by two wooden chairs with woven backs. A round black coffee table sits in the center, and a small side table is placed beside the sofa. Natural light filters into the space.

4.99 out of 5 average rating, 143 reviews

Modern, Light-Filled Capitol Hill 2BR w/ Parking

Apartment in Saint Michaels

A bright yellow building features large blue shutters and a welcoming entrance. A sign is placed outside, and vibrant flowers border the steps. In the background, another structure is visible, along with flags proudly displayed.

4.98 out of 5 average rating, 129 reviews

Blue Crab Lodge

4.95 out of 5 average rating, 108 reviews

Apartment in Takoma Park

Rustic 3BR Apt Stay | Minutes from D.C

Apartment in Mount Pleasant

A living area features a blue velour chaise lounge sofa and a stylish coffee table atop a light rug. A flat-screen TV is mounted on a wooden cabinet, which contrasts with the white brick walls. Natural light from windows illuminates the space, creating a welcoming ambiance.

4.99 out of 5 average rating, 400 reviews

Blue House by the Zoo- Mt. Pleasant-AdMo-CoHi

5 out of 5 average rating, 154 reviews

A modern living area is showcased, featuring a comfortable gray sofa with decorative cushions. A dark wooden coffee table sits in front, while a flat-screen TV is mounted on the wall. Framed artwork adds character to the bright, neutral-colored space.

Apartment in Georgetown

Luxury apartment in the heart of Georgetown

Apartment in Bloomingdale

A spacious living area features a neutral-toned sofa, accent chairs, and a decorative area rug. Artwork adorns the wall, and light fixtures provide bright illumination. A staircase leads to the upper level, while a full kitchen is visible in the background.

4.91 out of 5 average rating, 156 reviews

Stay in the heart of DC

4.98 out of 5 average rating, 143 reviews

Apartment in Takoma Park

Steps from D.C. | Peaceful 3BR Apt in Takoma Park

Holiday House Rentals with a Verandah

A waterfront home is depicted from the pier, showcasing a spacious screened porch with seating and an inviting entrance. Lush greenery surrounds the property, enhancing the natural setting. The wooden dock leads toward the house, creating a welcoming approach to the water.

5 out of 5 average rating, 37 reviews

Annapolis waterfront, private pier with kayaks

4.93 out of 5 average rating, 189 reviews

A welcoming living area features a comfortable sectional sofa with a cozy ottoman at the center, positioned on a soft area rug. Natural light fills the space through multiple windows, highlighting the vaulted ceiling with exposed beams and the decorative 'GATHER' sign on the wall.

Home in Edgewater

Spacious 3 Bedrooms House+Patio+Playground

5 out of 5 average rating, 200 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

A charming cottage exterior is framed by lush greenery and trees. A stone pathway leads to the front door, which is flanked by small plants and warm lighting. The deep blue color of the cottage contrasts with the surrounding nature, creating a serene atmosphere.

4.9 out of 5 average rating, 30 reviews

Annapolis Cottage

5 out of 5 average rating, 10 reviews

Cozy 3BR Annapolis, Private Deck, Parking

5 out of 5 average rating, 21 reviews

The exterior of the house features a combination of natural stone and shingle siding. A well-maintained garden with flowering shrubs borders the walkway. A small porch is visible, providing access to the entrance, all under a clear blue sky.

Home in Stevensville

Bay Bliss House

5 out of 5 average rating, 60 reviews

The exterior of a newly built house is depicted, showcasing a grey facade with stone accents. A manicured lawn extends in the foreground, while a porch with white railings and steps leads to the entrance. A tree is positioned near the driveway, with a waterfront view visible in the background.

Home in Stevensville

Away at the Bay: New Home on the Chesapeake Bay!

A tranquil bedroom features a spacious bed adorned with a patterned throw and neatly arranged pillows. A modern lamp and decorative mirror enhance the ambiance, while natural light enters through a unique shaped window. A soft towel is elegantly rolled on the bed.

4.93 out of 5 average rating, 191 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

Holiday condos with a patio

5 out of 5 average rating, 115 reviews

A spacious living room features two comfortable armchairs positioned near a round coffee table, which holds a decorative bowl and a selection of books. Warm light from a floor lamp complements natural light streaming through the large window, with framed artwork enhancing the walls.

Condo in Capitol Hill

Attractive one-bedroom unit on Capitol Hill

4.87 out of 5 average rating, 218 reviews

A small dining setup is present featuring a round table and two gray chairs. A framed black-and-white photograph decorates the wall, adding a modern touch. Natural light enters from a nearby window, illuminating the clean and simple design.

Condo in Capitol Hill

Sunny Apartment in Historic Capitol Hill

Condo in Ballston - Virginia Square

A modern living area features a dark grey sectional sofa and a matching coffee table, complemented by natural light filtering through vertical blinds. A small side table holds a lamp, while a plant adds a touch of greenery. The kitchen area is visible in the background.

4.88 out of 5 average rating, 145 reviews

Lovely 1-Bedroom Condo with Pool and City View

4.88 out of 5 average rating, 112 reviews

A modern kitchen showcases a marble-topped island with bar seating for three. Natural light illuminates the space, highlighting the wooden stools and kitchen essentials arranged on the shelves. A potted plant in the foreground adds a touch of greenery, enhancing the inviting decor.

Condo in Ellicott City

Historic Schoolhouse Condo

4.97 out of 5 average rating, 69 reviews

An open living area is showcased, featuring a light-colored sofa against a wall adorned with framed photographs. A large rug anchors the space, complemented by a round dining table and chairs. Natural light floods in from large sliding doors leading to a balcony.

Condo in Annapolis

Cozy Annapolis Condo

4.93 out of 5 average rating, 162 reviews

The image features a modern bathroom with a glass shower and striking exposed brick wall. Adjacent to the bathroom, a living area with wood beams highlights a Smart TV and comfortable seating. Natural light is provided through windows, enhancing an inviting atmosphere.

Condo in Navy Yard

DC’s Southwest and Navy Yard Welcomes You!

4.95 out of 5 average rating, 169 reviews

A bright living room features a textured brick wall and a cozy gray sofa adorned with decorative pillows. A glass coffee table sits atop a soft rug near a modern armchair. Natural light fills the space through large windows, enhancing the inviting atmosphere.

Condo in Capitol Hill

Light-filled Private Oasis / Close to Capitol Bldg