Annapolis Vacation Rental Homes By Owner

****Covid 19 updates - we are following all CDC guidelines ( and more ) *** ????New kitchen , 2 system central AC and Heat , parking spot , Master bath and deck... Read More

Set out to your perfect waterfront vacation rental at ‘The Pearl’, surrounded by vibrant Chesapeake Bay culture and a picturesque waterfront location! Leave this... Read More

0202 OFFICERS QUARTERS An Extraordinary Historic Home in the heart of downtown Annapolis. 0202 Officers Quarters is special. This beautifully renovated home of... Read More

DOWNTOWN ANNAPOLIS GEM Steps to the Naval Academy Gate and City Dock. This downtown gem has 4 bedrooms and 3 1/2 baths. A newly renovated kitchen opening to a... Read More

Beautifully restored, turn of the century, beach cottage rental in Annapolis located on an acre of landscaped property with magnificent views of the Chesapeake... Read More

About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this completely renovated, midcentury... Read More

This private single family home is located on a quarter acre of land and is just minutes to everything Annapolis has to offer. It is 10 minutes by car to downtown... Read More

Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome steps away from Gate One, City Dock... Read More

A perfect home to enjoy time in Annapolis! Located on King George Street, walking distance to the US Naval Academy or downtown, this home is open year round with... Read More

1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in downtown's Arts District, we are... Read More

Beautiful Remodeled Townhome ! We have thought of everything you will need for an amazing stay. Fully loaded kitchen , 3 and 1/2 Baths , Wonderful Upgraded... Read More

Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat for your upcoming trip . Light and airy ,... Read More

Lovely historic home within walking distance from downtown (1 mile from Church Circle) & Navy stadium (5 blocks), hardwood floors, remodeled kitchen & baths, tall... Read More

We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downtown .This location is the true center of... Read More

Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 mile to Naval Academy Stadium -1.5 miles... Read More

0025 BELLA CHATEAU ???????Lot's of space! Entertaining space, dining space, outdoor space and sleeping space. Warm and inviting social rooms for gathering and... Read More

THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay View! Luxurious newly built waterfront home with every amenity. Large Stone Porch & Second Floor... Read More

This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walking distance to USNA, Navy-Marine Corps... Read More

CONTACT OWNER FOR CW2024 RATES/BOOKING! Welcome to the heart of historic Annapolis! This charming home (City of Annapolis Rental License #141378) is just steps... Read More

*Still Available for 2022 Commissioning Week - Flexible Cancellation Policy* Just a quick drive to Downtown Annapolis, this gorgeous sun-drenched home in... Read More