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  • Large Contemporary in Wooded Privacy

    Annapolis, MD

    Lovely, contemporary sitting on three and-a-half acres of wooded beauty. Lots of glass and cedar. Open and airy floor plan. Sunken living room with see-through fire place. Huge glass windows and... ...more

    Beds: 5 Baths: 4 Property type: House (55)
    Select Dates for Price
  • Annapolis Condominium in the Heart of Historic Downtown

    Annapolis, MD

    Unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with two singles per room), living room with 42' flatscreen tv, stereo, kitchen with stainless... ...more

    Beds: 3 Baths: 2 Property type: Condo (106)
    $306 / Nightly
  • Charming Bay House in Private Beach Community

    Annapolis, MD

    Charming Bay Cottage just steps from a beautiful beach and the Chesapeake Bay, a short drive or walk to the crabbing and fishing pier and easy boat access at Sandy Point Park. The home is ranch... ...more

    Beds: 3 Baths: 3 Property type: House (22) Excellent
    $344 / Nightly
  • Historic District - 1 Block to Naval Academy & State House

    Annapolis, MD

    Located in the Historic District. This newly renovated home is just one block to the Naval Academy, City Dock and the State House. You will find your stay a perfect vacation get-away with the... ...more

    Beds: 2 Baths: 2 Property type: House (50)
    $330 / Nightly
  • WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS

    Annapolis, MD

    CHARMING FOUR BEDROOM WATERFRONT COTTAGE ON SCENIC SEVERN RIVER WITH STUNNING VIEWS -- RARE CLOSE-IN LOCATION - JUST MINUTES BY BOAT OR CAR TO DOWNTOWN HISTORIC ANNPOLIS AND U.S. NAVAL ACADEMY -... ...more

    Beds: 4 Baths: 2 Property type: Cottage (20) Wonderful
    $479 / Nightly
  • Heart of Downtown, superior location!

    Annapolis, MD

    Steps from the Annapolis City Dock and U.S. Naval Academy- Walk to all Shops, Restaurants, and Downtown Events. This property is on the Historic Register. Why reserve 3-4 hotel rooms when you can... ...more

    Beds: 4 Baths: 3 Property type: House (22) Excellent
    $712 / Nightly
  • Charming Historic Downtown Annapolis Cottage - Steps to USNA and City Dock

    Annapolis, MD

    Location, location, location. Half a block from the Naval Academy in the 'Sailing Capital of the US' and around the corner from City Dock, Market House, oldest operating State House in the... ...more

    Beds: 3 Baths: 2 Property type: Cottage (14) Exceptional
    $529 / Nightly
  • Gorgeous Luxury Home steps to USNA/State House/City Dock

    Annapolis, MD

    Hello and Welcome to Annapolis! Thanksgiving 2018 Week still available!!! PLEASE if you are inquiring about USNA Commissioning week please read the ENTIRE listing for info and quotes. The... ...more

    Beds: 3 Baths: 3 Property type: House (20) Wonderful
    $593 / Nightly
  • Stunning Home in the Historic District, Steps to the Academy

    Annapolis, MD

    A perfect home to enjoy time in Annapolis! Located on King George Street, walking distance to the academy or downtown, this home is open year round with a two night minimum stay. It is an... ...more

    Beds: 5 Baths: 5 Property type: House (48)
    $1,046 / Nightly
  • Historic District Home with Gorgeous Renovation

    Annapolis, MD

    When this home was renovated in 2008, no expense was spared to upgrade and decorate this house with every amenity. Cherry hardwood cabinets with stainless appliances and accents, granite counter... ...more

    Beds: 2 Baths: 3 Property type: House (40) Wonderful
    $481 / Nightly
  • Renovated Historic Home Located Downtown -Walk Everywhere!

    Annapolis, MD

    We welcome you to our fabulous row house on one of the most coveted areas in all of the Historic District !You will be delighted by this one of a kind home located right in the heart of Downtown... ...more

    Beds: 3 Baths: 2 Property type: House (134) Wonderful
    $291 / Nightly
  • Great For Entertaining!! with pool!! 1 mile from downtown!

    Annapolis, MD

    This home is perfect for all occasions...reunions, weddings, graduations. Walking distance to all shopping and Navy events. Very comfortable living. Very spacious!!.....Gorgeous pool in the private... ...more

    Beds: 5 Baths: 5 Property type: House (18) Wonderful
    $1,132 / Nightly
  • Stunning Annapolis Home! Available 2019 USNA Commisioning Week!

    Annapolis, MD

    This 4 BR, 4.5 BA house is perfect for entertaining your guests! Come into our spacious open floor plan. The entertainment area has 2 large flat screen TV's to watch any sporting event. You feel... ...more

    Beds: 4 Baths: 5 Property type: House (38)
    $971 / Nightly
  • Annapolis Historic District Apartment

    Annapolis, MD

    This very well maintained apartment is very comfortably furnished and accomodates all live-in needs. Sleeps 4-5. (queen sized bed, NEW(2016)queen sized sleeper sofa, (1)roll away hide-a-bed) This... ...more

    Beds: 1 Baths: 1 Property type: Apartment (56) Wonderful
    $251 / Nightly
  • Walk to Navy Stadium; plenty of FREE unrestricted parking; impeccable home

    Annapolis, MD

    Easy walking distance to Navy-Marine Corps Stadium (perfect location for Commissioning Week!), located 1 mile (5 minutes by cab or car) from Church Circle in the heart of historic downtown... ...more

    Beds: 5 Baths: 5 Property type: House (41) Wonderful
    $748 / Nightly
  • Annapolis Historic District Apartment

    Annapolis, MD

    Front Apartment This very well maintained apartment is very comfortably furnished and accomodates all live-in needs. Sleeps 4-5. (queen sized bed, queen sized sleeper sofa, (1)roll away... ...more

    Beds: 1 Baths: 1 Property type: Apartment (55) Wonderful
    $250 / Nightly
  • Charming historic home just steps from Main Street!

    Annapolis, MD

    AVAILABLE FOR COMMISSIONING WEEK2021! Welcome to the heart of historic Annapolis! This charming home (City of Annaplis Rental License #141378) is just steps from Main Street, a block from the... ...more

    Beds: 3 Baths: 3 Property type: House (102)
    $553 / Nightly
  • Beautiful Annapolis Getaway - Walk Everywhere, Parking & Private Backyard!

    Annapolis, MD

    Absolutely Charming! Guests will feel right at home in this beautifully renovated 3+ bedroom/2 bath bungalow. Coastal cottage/Pottery Barn decor throughout; expansive gourmet kitchen facing a... ...more

    Beds: 3 Baths: 3 Property type: House (119)
    $575 / Nightly
  • Historic Annapolis -1 RESERVED PARKING SPACE INCLUDED! Two blocks to Main Street

    Annapolis, MD

    Welcome to the heart of Historic Annapolis...charming and quaint, beautiful tree lined streets, brick sidewalks, and rich colonial history...all situated on the Chesapeake Bay. Our home is a... ...more

    Beds: 3 Baths: 2 Property type: House (44)
    $461 / Nightly
  • Historic Annapolis Home And Garden

    Annapolis, MD

    This delightful two bedroom, two full bath duplex occupies the second and third floors of a lovely home built in 1900, under the dome of the USNA Chapel. A beautiful park-like garden behind the... ...more

    Beds: 2 Baths: 2 Property type: House (24)
    $357 / Nightly
Search result 1 to 20 Of 178

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Annapolis. Many accommodations in Annapolis provide "Pets Not Allowed", there are 227, or there are 191 of Vacation Rentals in Annapolis with a "Non Smoking Only", there are also 137 with a "Children Welcome", which is another great reason to visit Annapolis.