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.

5 out of 5 average rating, 122 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, 171 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, 187 reviews

The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

5 out of 5 average rating, 103 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.

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, 117 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, 106 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, 116 reviews

Welcome to Annapolis-very 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.

4.92 out of 5 average rating, 108 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.

4.98 out of 5 average rating, 102 reviews

Charming Annapolis Waterfront Condo

Discover the charm of CAPTAINS QUARTERS, your exclusive waterfront retreat in the prestigious Yacht Club Condominiums. Steps from Downtown Eastport and Annapolis, this gem offers stunning views, a community pool, and the essence of luxury. With 2 free parking spots, you're 1.6 miles from the Naval Academy and under a mile to Downtown Annapolis attractions. Perfectly positioned for exploration or relaxation, your stay promises an unmatched Annapolis experience.

A charming exterior showcases a historic two-story row house painted in green and blue. The red door adds a vibrant touch, while brick pavement leads to the entrance. Nearby planters and greenery enhance the welcoming appearance, with utility lines and neighboring houses visible in the background.

4.96 out of 5 average rating, 134 reviews

Green On Fleet - Rowhouse in Historic Annapolis

Welcome to Green on Fleet ! This adorable historic row house has an amazing location less than one block from City Dock and two blocks from USNA etc. Recently renovated with style we feature two bedrooms and one and a half baths with two floors and an outdoor patio. Walk to all Annapolis has to offer (USNA,AYC, City dock, Paca House, area churches etc). Our guests use one of the City pay garages to park . Hillman is closest Insta: @green_on_fleet

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, 167 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!

Guest house 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, 366 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

4.95 out of 5 average rating, 204 reviews

A bright living area features a blue L-shaped sofa, accompanied by an accent chair. Artwork hangs on the white walls, while large windows invite natural light and showcase the outdoor patio area with seating.

Flat in Old Town

1/2 Block From King Street, King Bed Free Parking

4.97 out of 5 average rating, 172 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, 165 reviews

Flat in Upper Marlboro

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

4.95 out of 5 average rating, 100 reviews

A two-story house is set against a backdrop of clear blue sky and lush greenery. A spacious deck is visible at the back, featuring a vibrant red umbrella. Well-maintained grass surrounds the home, punctuated by several trees for added privacy.

Flat in Mt. Washington

Mother-in-law suite with yard

4.97 out of 5 average rating, 116 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

4.99 out of 5 average rating, 144 reviews

A modern living area features a vibrant teal sofa, complemented by a patterned area rug. Two stylish chairs are placed across from a concrete coffee table. Soft lamps illuminate the space, and a framed artwork hangs on the dark wall, enhancing the room's contemporary aesthetic.

Flat in Old Town North

King Bed <|> A Stylish Executive Suite Xcape

4.97 out of 5 average rating, 162 reviews

A bright sleeping area features a queen-sized bed with a light-colored quilt and decorative pillows. Two nightstands with lamps are positioned on either side of the bed against a bold turquoise wall. Framed artwork and a small plant add a touch of character to the room.

Flat in Del Ray

Cute room, basic kitchenette & deck! Pet friendly

4.99 out of 5 average rating, 354 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

House rentals with a patio

A three-story house is set within a landscaped yard, featuring a brick walkway leading to a covered entrance. Lush greenery and flowering plants enhance the inviting exterior, while a large blue awning provides shade over the front porch.

4.98 out of 5 average rating, 50 reviews

West street historic home

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

A spacious living area showcases a comfortable sectional sofa and a leather armchair beside a decorative rug. A modern fireplace is framed by a white mantel, while a large television is mounted on the wall. A view of the stylish kitchen is visible in the background.

4.97 out of 5 average rating, 77 reviews

Downtown Annapolis Luxury House

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, 11 reviews

The Lighthouse: Walk to stadium, downtown, West St

A spacious living room features a comfortable gray sofa, two accent chairs, and a wooden coffee table. Natural light streams in through large windows covered by light curtains, while a vibrant plant adds a touch of greenery. A wall-mounted television and artwork of a boat enhance the decor.

4.96 out of 5 average rating, 48 reviews

Cute Downtwn Townhouse *Onsite Parking* & Patio!

The living room features a curved teal sectional sofa, a light wooden coffee table, and a beige accent chair. Artwork is displayed on the wall above the sofa. A soft area rug adds warmth, and natural light is present from an unseen window.

5 out of 5 average rating, 25 reviews

Newly Renovated Downtown Charm, Game Room, Patio

5 out of 5 average rating, 27 reviews

Home in Pasadena

Rock Creek Cottage, Waterfront

A bright kitchen is designed with white cabinetry and an expansive island featuring a marble countertop. Two pendant lights hang above the island, which is paired with wooden stools. Natural light filters through the window, illuminating the stainless steel appliances and organized countertops.

4.96 out of 5 average rating, 28 reviews

Captain's Retreat, Outdoor Oasis <10 mins USNA

Apartment rentals with a patio

Superhost

A modern living area is showcased with a cozy sofa and two armchairs arranged around a wooden coffee table. A small workstation is positioned against the wall, while light filters in through multiple windows. A patterned area rug adds texture to the space.

Apartment in Bloomingdale

4.89 out of 5 average rating, 139 reviews

Renovated&bright 1-bedroom in heart of DC

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, 111 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.

4.86 out of 5 average rating, 189 reviews

Sunny Apartment in Historic Capitol Hill

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, 68 reviews

Cozy Annapolis Condo

Superhost

A cozy bedroom is highlighted by a spacious bed, adorned with a light blue bedspread and decorative pillows. Flanking the bed are two nightstands with lamps, and a colorful area rug adds warmth to the hardwood floor.

Apartment in Petworth

4.93 out of 5 average rating, 217 reviews

Unique, charming garden apartment