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, 120 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, 208 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!

5 out of 5 average rating, 186 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, 101 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.

A charming single-story house is presented with a light gray exterior and a prominent teal door. Symmetrical landscaping frames the entrance, featuring neatly trimmed hedges and colorful plants. A concrete pathway leads to the front steps, inviting guests into a welcoming atmosphere.

4.95 out of 5 average rating, 110 reviews

Charming Annapolis Retreat with Hidden Wine Room

Discover charm in our 2BR, 1BA Eastport home, just a stroll away from downtown Eastport (under 1 mile), Downtown Annapolis (1.3 miles), the Naval Academy (2.3 miles), and less than 3 miles to Navy Stadium. Relax on our screened porch, by the fire pit, or under the cozy cabana out back. Delight in a secret—a hidden wine cellar awaits below! Plenty of free parking under the carport or on the street. Plus, with the water taxi service at the nearby dock, the best of Annapolis is just a call away.

Houseboat in Kent Narrows

A modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.

4.97 out of 5 average rating, 172 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

4.92 out of 5 average rating, 156 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

Spacious 3 bedrooms house with functional patio + private playround located in Edgewater, only 15 mins drive to downtown Annapolis. Fully equipped with designer furnitures, with a sense of home! Huge dining room and fully functional kitchen, perfect to enjoy a great evening with your friends and family! Bedrooms are equipped with your own desks if you want to do some works even in your vacation. Easily fit 2 cars in private driveway. Very quiet neighborhood with proximity to everything!

4.85 out of 5 average rating, 155 reviews

Outdoor seating is provided under a wooden pergola, featuring four stylish chairs and a table. A patterned area rug enhances the space, while potted plants add greenery. Bright cushions bring a pop of color, inviting guests to relax among the surrounding trees.

Guest suite in Arnold

Cozy Comfort Close to Annapolis & USNA

Private first-floor 2- bedroom guest apartment, a quiet retreat in a lovely residential neighborhood 7.5 miles to Annapolis & USNA. Large living room, mini sit-in kitchen, bathroom, and laundry room. It’s ideal for travelers who want privacy, and a little more space than the usual stay. Sip your morning coffee in the gazebo and unwind after day trips fireside on the comfy sectional. The kitchen is ideal for enjoying light cooking or take outs. Comfy queen sized beds with crisp linens.

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.

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, 164 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!

4.93 out of 5 average rating, 199 reviews

A serene backyard space features a rectangular pool surrounded by a spacious patio. Lounge chairs are positioned near the water, with a shaded gazebo offering seating nearby. The area is bordered by lush greenery, providing a sense of privacy and tranquility.

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Our pool is closed for the season; however, our hot tub is open! Ideal for a couple's retreat, this king suite guest room has a seating area, mounted TV, and coffee bar, microwave, and mini-fridge. An ensuite bathroom provides a luxurious shower and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

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, 363 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, 168 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

4.94 out of 5 average rating, 161 reviews

Flat in Upper Marlboro

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

4.99 out of 5 average rating, 128 reviews

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.

Flat in Capitol Hill

New Light-Filled Cap Hill Apt (2 BD)+ Parking

4.99 out of 5 average rating, 169 reviews

A cozy living area showcases a deep blue accent wall, paired with a plush blue sofa and gold floor lamp. A light area rug covers the wood floor, while a white coffee table is centered in the space. French doors lead to a balcony, allowing natural light to fill the room.

Flat in Old Town North

King Bed <|> A Deluxe Suite Xcape w/Private Office

4.85 out of 5 average rating, 148 reviews

A cozy sleeping area features a large bed adorned with soft gray linens and decorative pillows. Tropical patterned wallpaper adds visual interest, while a wooden coffee table with a round bowl is positioned in front. Two bedside lamps provide gentle illumination.

Flat in Penrose

Palm Suite: Private Lower Level Studio Near DC

4.97 out of 5 average rating, 157 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, 352 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

4.92 out of 5 average rating, 106 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

House rentals with a patio

The image captures a charming row of historic townhomes along a brick-paved street. Each home features a distinct color, with red, white, yellow, and green facades. The welcoming front doors are flanked by small, round planters, adding a touch of greenery to the vibrant neighborhood.

5 out of 5 average rating, 16 reviews

Naval Academy Gate 1

4.85 out of 5 average rating, 60 reviews

A cozy living room features a brown sofa placed alongside a light-colored coffee table. Two blue chairs with yellow cushions are positioned across from the sofa. A large window allows natural light to fill the space, with greenery visible outside. A ceiling fan adds to the comfort.

Home in Arnold

Cozy Arnold House Near Annapolis

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!

4.97 out of 5 average rating, 37 reviews

Home in Odenton

Train Tracks Getaway (Whole house)

4.92 out of 5 average rating, 25 reviews

A welcoming single-story home with a light green exterior and brick accents is seen. The front yard features well-maintained shrubs and a lawn with fallen leaves. Large windows allow natural light to illuminate the interior, and a porch leads to the front door.

Home in Glen Burnie

Glen Burnie Hideaway

A welcoming living space is highlighted by natural light streaming through large windows. A light beige sofa is positioned alongside a wooden dining table with a yellow décor piece. A bright yellow door provides a striking focal point, complementing the greenery in the room.

5 out of 5 average rating, 14 reviews

Historic + Modern Home | Just Steps to Waterfront

4.84 out of 5 average rating, 64 reviews

A living room is presented featuring a comfortable seating arrangement with two white armchairs and a gray sofa. A wooden coffee table is centrally placed. The room includes a decorative fireplace framed by artwork, a television, and a tall lamp, all set against light-colored walls.

Home in Edgewater

Sunset Corner House

4.97 out of 5 average rating, 29 reviews

The exterior of the townhome features a well-maintained front yard with lush greenery and a concrete pathway leading to the entrance. The two-story building has a light-colored facade and an inviting appearance, framed by trees.

Home in Arnold

Cozy Townhouse Minutes from Downtown Annapolis

Apartment rentals with a patio

Apartment in Bloomingdale

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.

4.89 out of 5 average rating, 139 reviews

Renovated&bright 1-bedroom in heart of DC

Apartment in Capitol Hill

A well-lit living area is featured, showcasing a comfortable sectional couch and a wooden dining table surrounded by light blue chairs. A television is positioned against the wall, and decorative elements such as framed artwork and a bookshelf add character to the space.

4.93 out of 5 average rating, 59 reviews

Cozy Capitol Hill Row Home

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, 187 reviews

Sunny Apartment in Historic Capitol Hill

4.97 out of 5 average rating, 67 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.

Apartment in Annapolis

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

4.93 out of 5 average rating, 151 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!