House holiday rentals 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, 138 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.

4.98 out of 5 average rating, 176 reviews

Two adirondack chairs in blue and teal are positioned on a wooden pier, facing the sunset over calm waters. A small white table sits between them, holding two coffee mugs. The vibrant orange and pink hues of the sky reflect on the water's surface.

Home in Edgewater

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

An inviting living room showcases a light-colored sectional sofa adorned with decorative pillows. A wooden coffee table, accompanied by a small ottoman, sits on warm hardwood flooring. Natural light filters through the window near the front door, which features glass panels.

4.93 out of 5 average rating, 360 reviews

Cozy 2br home w/ parking in downtown Annapolis

Ideally located in the heart of downtown Annapolis's Historic & Art Districts. Detached home with historic charm & an inviting front porch, 1 car parking included. Open floor plan to include a living room (with queen sleeper sofa), workspace, 1/2 bath & eat in kitchen on the 1st floor. 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. A perfect location for C-Week, Boat Shows & other festivals in Historic Annapolis.

5 out of 5 average rating, 105 reviews

Quaint in the Heart of Annapolis

Quaint 2 bedroom, 1 bath home located in the heart of historic Annapolis. Completely remodeled with free off-street parking. Located towards the end of a safe, quiet, dead end road, less than 3 miles from downtown Annapolis, the Naval Academy, the Annapolis Mall, St. John’s College, and the Navy-Marine Corps Memorial Stadium. Walk downtown or to the Annapolis Town Center, restaurants, shops, and so much more! -Wi-Fi -2 free parking spaces -Keurig Coffee -TV -Toothbrushes/Paste -Shampoo/Soaps

4.99 out of 5 average rating, 136 reviews

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

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, 164 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

The open-concept living space features hardwood floors and large windows allowing natural light. A neutral-colored sofa with side cushions is positioned near a coffee table. A dining table accommodates multiple guests, while the kitchen showcases modern appliances and cabinetry.

4.98 out of 5 average rating, 125 reviews

Charming Downtwn Home- Private Parking Patio&Yard!

Welcome home to this Annapolis gem. An adorable 1930 American foursquare with private driveway, located on a quiet cul-de-sac off in downtowns Art's District. This cozy, three bedroom home can hold you and nine guests with plenty of sleeping arrangements for everyone. Enjoy a spacious backyard patio with string lights and deck chairs giving you and your guests plenty outdoor entertaining options. This house is fully furnished. Short walk to everything downtown offers, it just needs you!

A cozy living room features a large sectional sofa adorned with soft pillows. A coffee table sits in the center on a vibrant area rug. A television is positioned on a side table, with natural light coming through the windows. The entrance door adds warmth to the space.

4.94 out of 5 average rating, 214 reviews

Chesapeake Comfort, Annapolis.

Veteran Superhost! Annapolis Bungalow Home. Professionally cleaned and a full time Airbnb. I have been a Superhost with my listings for over 10 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch. Queen Bedroom on ground floor. 2nd Queen Bedroom on lower level w/bathroom. Loft bedroom has 2 full size beds.

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.

4.98 out of 5 average rating, 132 reviews

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!

The front porch features a welcoming red door and blue Adirondack chairs. Stone steps lead to the porch, adorned with a large pot of yellow flowers and a matching red planter. White railings frame the porch, enhancing its charming appearance.

4.99 out of 5 average rating, 180 reviews

Charming house; walk to everywhere in Annapolis

Charming historic house, private and upscale, tucked away in the quiet President’s Hill neighborhood, located off West Street (Annapolis Arts District) with many restaurants. City Dock/Navy Stadium within walking distance. Free shuttle bus to downtown. Enjoy entire house, including front porch and back yard garden sanctuary with water pond. Peace and nature abound! House is fully stocked for cooking including all basics (spices, oil/vinegar), coffee/tea. You will feel at home here!

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, 189 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 serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.

4.97 out of 5 average rating, 235 reviews

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.

Popular amenities for house rentals in Annapolis

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 164 reviews

A winding stone pathway leads through a vast green lawn towards the shimmering waters of the eastern Chesapeake Bay. Two comfortable lounge chairs are positioned at the water's edge, offering a serene view of the horizon under a soft blue sky.

Home in Queenstown

Bay Breeze Retreat

4.97 out of 5 average rating, 129 reviews

An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.

Home in Cambridge

Gorgeous, Waterfront Home Is Fabulous in Winter!

4.99 out of 5 average rating, 78 reviews

A spacious backyard features a pool surrounded by a paved patio. Comfortable lounge chairs and umbrellas are positioned for relaxation. The two-story house with a deck overlooks the inviting pool area, flanked by lush greenery and colorful landscaping.

Home in Edgewater

Entire Beach House with Pool and Hot Tub

4.88 out of 5 average rating, 207 reviews

A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.

Home in Severn

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

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

4.99 out of 5 average rating, 129 reviews

The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.

Home in Perry Hall

Gunpowder Retreat

4.89 out of 5 average rating, 203 reviews

A large in-ground pool is surrounded by tall trees and a secured wooden fence. Colorful pool floats float on the water's surface, enhancing the inviting atmosphere of the outdoor space. A landscaped lawn provides ample green space for relaxation.

Home in Fort Washington

5 BEDR, Inground Pool+Billiard Table, Close To D.C

4.88 out of 5 average rating, 112 reviews

A stylish dining area is showcased, featuring a long table set for a meal. Generous seating is provided by a custom velvet upholstered bench with decorative pillows, while a modern light fixture hangs above. Large windows allow natural light to fill the space.

Home in Bowie

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

Weekly house rentals

An open living area showcases a spacious kitchen with modern appliances and a large island. Comfortable seating is arranged around a decorative rug, while a flat-screen TV is mounted on the wall. Natural light brightens the room through multiple windows.

4.95 out of 5 average rating, 61 reviews

Cute bungalow blocks to Stadium

5 out of 5 average rating, 7 reviews

Downtown Annapolis Charming 2 BDR Townhome

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, 34 reviews

Historic + Modern Home | Just Steps to Waterfront

The exterior of a charming, newly renovated home features a welcoming front porch, adorned with bright rockers. Lush greenery and colorful flowers line the walkway, enhancing the inviting appearance against a backdrop of soft evening light.

5 out of 5 average rating, 44 reviews

The Midship Quarters

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, 26 reviews

Newly Renovated Downtown Charm, Game Room, Patio

5 out of 5 average rating, 11 reviews

The Anchored Stay: Spacious, Walkable & Parking

The outdoor patio features a herringbone flagstone design, a modern fire pit surrounded by gray gravel, and a built-in seating area. A hanging swing chair is suspended nearby, while greenery and flowers add a natural touch to the landscaped yard.

4.96 out of 5 average rating, 50 reviews

Eastport Oasis

5 out of 5 average rating, 31 reviews

Perfect Location! 200 steps to USNA & Downtown

Private house rentals

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.

4.98 out of 5 average rating, 86 reviews

Downtown Annapolis Luxury House

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, 20 reviews

Historic Downtown Annapolis w/ Rooftop Deck

The exterior of a charming historic home is illuminated at dusk, with warm lights glowing from the windows. A spacious front porch is visible, and a well-maintained garden with shrubs and plants frames the entrance. The nearby deck area features string lights for ambiance.

4.92 out of 5 average rating, 39 reviews

Waterfront Home - Amazing Views - Beach Adjacent

A grassy yard extends to the water's edge, featuring several Adirondack chairs arranged for relaxation. Paths made of circular stones lead towards a private pier, where boats can be seen docked. Visible kayaks suggest opportunities for outdoor activities.

4.99 out of 5 average rating, 69 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

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

A serene bedroom is furnished with a spacious bed dressed in crisp white linens and a navy throw blanket. Two bedside tables with stylish lamps flank the bed, and a large mirror reflects the room's light. A flat-screen TV is mounted on the wall.

4.98 out of 5 average rating, 40 reviews

Admiral’s Landing: Walk to Naval Academy, West St.

The screened porch is illuminated by soft lighting, featuring comfortable seating and a dining table. Large windows provide a view of the interior space, while a pathway leads to the entrance. The wooded surroundings create a serene backdrop for outdoor enjoyment.

4.98 out of 5 average rating, 59 reviews

Annapolis Cottage at Bay Ridge, Renovated

The living room showcases large windows that provide ample natural light and offer views of the surrounding area. A comfortable blue velvet sofa is paired with two light-colored armchairs and a wooden coffee table, creating a welcoming seating arrangement on a light-colored area rug.