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, 133 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.

4.95 out of 5 average rating, 228 reviews

Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

4.96 out of 5 average rating, 180 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.

The spacious living area features a dark leather sectional sofa, complemented by wooden beams overhead. A large TV is mounted above a fireplace, and a dining area is visible in the background. Natural light floods the space, enhancing the welcoming atmosphere.

4.97 out of 5 average rating, 127 reviews

4 bedrooms, 7 beds, 3 bath completely updated

Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of home, without having to bring them yourself. Full kitchen with fresh coffee beans, K cups, and tea provided for starters. Breakfast starters provided too. Everything you need if you want to cook. Games for inside (including PS5), and backyard games too. 3 bedrooms on ground floor so no constantly having to go up and down steps. We love our place and know you will too.

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.

4.96 out of 5 average rating, 111 reviews

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

A spacious living area is depicted with plush teal seating arranged around a coffee table. A modern entertainment unit is positioned against a wall, while large sliding doors open to a private balcony. Natural light enhances the warm tones of the decor.

4.97 out of 5 average rating, 117 reviews

1 bedroom -king in Annapolis- low cleaning fee

Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

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.

Flat 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.

4.92 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.

Flat 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.

4.94 out of 5 average rating, 203 reviews

Guest suite in Arnold

Affordable, Cozy Retreat 4 Miles from Annapolis

*New hot tub and pergola installed!* Escape to a cozy, modern retreat just 4 miles from downtown Annapolis. This intimate king suite offers a private seating area, kitchenette, & TV. The ensuite bathroom features a luxurious shower. Relax in peace and comfort after exploring Annapolis or attending local events. Please note that the pool and hot tub are closed for the season. Reach out anytime with questions or special requests—we’re happy to help make your stay memorable!

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, 183 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!

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.

4.96 out of 5 average rating, 126 reviews

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, 382 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 rentals with patio in Annapolis

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

4.96 out of 5 average rating, 193 reviews

A light-filled living space features a large, plush sectional sofa adorned with decorative pillows. A round coffee table sits at the center, surrounded by a tasteful area rug. A small dining area is visible, with a wooden table and chairs, and greenery is provided by a nearby potted plant.

Flat in Washington

Subway & Easy Parking! Sunny 2 Bdrm w/ King Bed

4.95 out of 5 average rating, 187 reviews

Flat in Upper Marlboro

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

4.94 out of 5 average rating, 260 reviews

A spacious living area features two comfortable seating arrangements, a small desk with a chair, and a decorative tree stand. Natural light enters through two windows, adding warmth. A small table holds magazines, while a sliding door leads to an outdoor area.

Flat in Capitol Hill

Spacious Capitol Hill Apartment

4.98 out of 5 average rating, 128 reviews

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.

Flat in Saint Michaels

Blue Crab Lodge

4.95 out of 5 average rating, 104 reviews

Flat in Takoma Park

Rustic 3BR Apt Stay | Minutes from D.C

4.97 out of 5 average rating, 192 reviews

Flat in Del Ray

Cute room, kitchenette & deck! Heart of Del Ray

4.99 out of 5 average rating, 391 reviews

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.

Flat in Mount Pleasant

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

5 out of 5 average rating, 149 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.

Flat in Georgetown

Luxury apartment in the heart of Georgetown

House rentals with a patio

A lush green yard borders a calm body of water, where a private pier is visible. Flower beds with white and pink blooms add color to the scene. A small boat is moored at the pier, with trees providing shade along the waterfront.

4.97 out of 5 average rating, 90 reviews

Annapolis USNA Waterfront Cottage w/Pier & Firepit

5 out of 5 average rating, 106 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

A bright living area features a dark leather sofa and a cozy chair, complemented by a geometric area rug. Large windows provide natural light, while a flat-screen TV is mounted on the wall. A round coffee table holds magazines, creating an inviting space for relaxation.

5 out of 5 average rating, 26 reviews

The Lighthouse: Walk to stadium, downtown, West St

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, 36 reviews

Annapolis waterfront, private pier with kayaks

A modern living area features a spacious gray sectional sofa, complementing two navy blue armchairs. A round coffee table sits in the center, adorned with fresh flowers. Natural light enters through multiple windows, and a decorative sailboat painting adds a nautical touch to the light gray walls.

4.95 out of 5 average rating, 22 reviews

Sailor's Retreat

4.92 out of 5 average rating, 12 reviews

The Gloucester House

Superhost

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

4.9 out of 5 average rating, 186 reviews

Spacious 3 Bedrooms House+Patio+Playground

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

Apartment rentals with a patio

4.96 out of 5 average rating, 57 reviews

An open-concept living area features a spacious layout with natural light illuminating the room. A comfortable dark sofa adorned with decorative pillows faces an inviting dining table. Sleek kitchen cabinets and modern appliances are evident in the background, while a sliding door leads to a private deck.

Apartment in Deanwood

True Gem: Spacious-Modern-2 King Beds-PRKG-Deck

Apartment in Capitol Hill

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.

5 out of 5 average rating, 113 reviews

Attractive one-bedroom unit on Capitol Hill

Apartment in Capitol Hill

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.

4.87 out of 5 average rating, 213 reviews

Sunny Apartment in Historic Capitol Hill

Superhost

Apartment in Downtown Silver Springs

4.82 out of 5 average rating, 11 reviews

Walkable Downtown DC Metro Skyline Suite | LuxePad

Apartment in Ellicott City

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.

4.88 out of 5 average rating, 112 reviews

Historic Schoolhouse Condo

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.

4.97 out of 5 average rating, 69 reviews

Cozy Annapolis Condo

4.93 out of 5 average rating, 161 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.

Apartment in Navy Yard

DC’s Southwest and Navy Yard Welcomes You!