Holiday rentals with a patio in Parole

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, 126 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, 220 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, 104 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, 124 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.

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, 180 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

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, 110 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, 118 reviews

1 bedroom -king in 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, 113 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.

4.86 out of 5 average rating, 162 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, 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.

4.94 out of 5 average rating, 195 reviews

A spacious sleeping area features a king bed with a light-colored coverlet, accompanied by bedside lamps on either side. A colorful nautical painting adorns the blue accent wall, while ample natural light fills the room through a window, which is set behind the bed.

Guest suite in Arnold

Cozy 1-Bedroom Retreat Near Annapolis, Sleeps 4

This fully updated suite is designed for comfort and 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!

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, 118 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, 380 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 Parole Holiday Houses with Outdoor Verandahs

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.97 out of 5 average rating, 184 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.

Apartment in Washington

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

4.95 out of 5 average rating, 218 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.

Apartment in Old Town

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

Apartment in Upper Marlboro

A modern kitchen features warm wooden cabinetry, a sleek black stove, and a variety of kitchen appliances. A rustic dining table sits in the foreground, adorned with a woven runner and a wooden tray holding fresh fruit. The space is complemented by decorative shelves and natural light.

4.95 out of 5 average rating, 181 reviews

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

Superhost

A cozy living area features a leather sofa accented with patterned cushions. A black coffee table sits on a textured rug, while a flat-screen TV is mounted on the wall. Natural light enters through a window with blinds, illuminating the warm wooden flooring.

Apartment in Federal Hill - Montgomery

4.82 out of 5 average rating, 179 reviews

Charming Federal Hill! One Bedroom With Vibes

Apartment in Old Town North

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.

4.99 out of 5 average rating, 151 reviews

King Bed <|> A Stylish Executive Suite Xcape

4.97 out of 5 average rating, 183 reviews

Apartment in Del Ray

Cute room, basic kitchenette & deck! Pet friendly

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, 374 reviews

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

4.93 out of 5 average rating, 109 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

Holiday House Rentals with a Verandah

4.89 out of 5 average rating, 18 reviews

Nautical Cottage in Annapolis

4.92 out of 5 average rating, 255 reviews

A well-decorated bedroom features a spacious bed with neutral bedding. Nearby, a dresser with multiple drawers provides storage. Dual windows allow natural light, complemented by blinds for privacy. A vibrant area rug adds a pop of color, while a ceiling fan enhances air circulation.

Home in Stevensville

Relax on Kent Island in 4 Bedroom Home w/Waterview

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, 22 reviews

The Lighthouse: Walk to stadium, downtown, West St

4.79 out of 5 average rating, 189 reviews

The studio features a queen size bed adorned with a yellow floral blanket, located near a flat-screen TV mounted on the wall. A comfortable futon and a small coffee table complement the seating area, which also includes a fridge and microwave.

Home in Queens Chapel

Cozy Studio in NE DC

A spacious living area features a custom stone fireplace, surrounded by soft seating and a rustic coffee table. Large glass doors provide views of the outdoor space. A ceiling fan adds to the comfortable ambiance, while a large clock adorns the wall.

5 out of 5 average rating, 22 reviews

Marymont Cottage

4.82 out of 5 average rating, 67 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

4.94 out of 5 average rating, 113 reviews

The kitchen features modern appliances, including a stainless steel refrigerator and stove. White cabinetry complements the wood-like floor, while a small island offers additional counter space. A welcome mat is positioned near the entrance, contributing to an organized and functional environment.

Home in District Heights

The Lemon Drop

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, 139 reviews

Green On Fleet - Rowhouse in Historic Annapolis

Holiday condos with a patio

4.94 out of 5 average rating, 88 reviews

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.

Condo in Capitol Hill

Cozy Capitol Hill Row Home

5 out of 5 average rating, 112 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

5 out of 5 average rating, 42 reviews

A living space features a Chesterfield leather sofa and two orange accent chairs, arranged around a glass coffee table atop a patterned rug. The area is warmly lit by recessed lighting, with a glimpse of the bedroom area visible in the background.

Condo in Petworth

NWDC Jewelbox Deluxe 1BDR + Free Parking

5 out of 5 average rating, 21 reviews

A bright living area features a spacious gray couch positioned near a large window, which floods the room with natural light. A flat-screen television is mounted on the wall, while a stylish area rug sets a cozy tone beneath a small coffee table.

Condo in Washington

Penn Branch Oasis: Near Capitol Hill-King Bed-PRKG

4.87 out of 5 average rating, 203 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

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, 223 reviews

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.

Condo in Petworth

Unique, charming garden apartment