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Annapolis Vacation Rentals

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    Travelers to Annapolis are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 25
    5 of 5 bubbles (15) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    4.5 of 5 bubbles (3) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,... View all property information
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    Annapolis, Maryland 21403
    1 / 23
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available... View all property information
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    Annapolis, Maryland 21403
    1 / 15
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    Walk to the city docks and naval academy in this new (2014) luxury townhouse. The king bedroom suite also has a pullout twin bed for parents with small children. Enjoy the grand piano or relax by the gas fireplace. Cookout on the sunny patio. Visit local pubs and restaurants or just walk to... View all property information
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    Annapolis, Maryland 21403
    5 of 5 bubbles Reviewed November 16, 2016
    Beautifully decorated. Walking distance to Naval Academy. Plenty of sleeping space. Private outdoor space.
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Annapolis, Maryland 21403
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Annapolis, Maryland 21403
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liquor store and... View all property information
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    Annapolis, Maryland 21401
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    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Annapolis, Maryland 21401
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21403
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Annapolis, Maryland 21401
    1 / 19
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Annapolis, Maryland 21401
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    Annapolis, Maryland 21401
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Annapolis, Maryland 21409
    1 / 18
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 20
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21403
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    1 / 4
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    My place is good for couples, solo adventurers, and business (URL HIDDEN) school just down the street , Great location for naval academy parents for parents day etc. A gourmet kitchen if you prefer to cook your own meals or cook your fish you have caught on your fishing trip on the bay,we can... View all property information
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    Annapolis, Maryland 21403
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21409
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    Annapolis, Maryland 21401
    1 / 10
    2 Bedrooms, 15 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    Studio, 2 Bathrooms, Sleeps 18 | Quick View
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    Annapolis, Maryland 21409
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,... View all property information
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    Annapolis, Maryland 21403
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21409
    1 / 24
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Annapolis, Maryland 21409
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Waterfront
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    About this property
    Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will love waking up to views of... View all property information
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    Annapolis, Maryland 21032
    1 / 14
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    5 of 5 bubbles (3) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Porch
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    About this property
    The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms... View all property information
    Location Information
    Annapolis, Maryland 21405
    5 of 5 bubbles Reviewed October 21, 2015
    Our group of 6 couples rented this lovely home during the Annapolis, MD Annual Powerboat Show. Having stayed in hotels for prior boat shows, we wanted to have the freedom and...
    5 of 5 bubbles Reviewed September 27, 2014
    Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
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    1 / 24
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    Annapolis, Maryland 21401
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    Annapolis, Maryland 21401
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    HOUSE<BR>This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous... View all property information
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    Annapolis, Maryland 21403
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Annapolis, Maryland 21401
    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Annapolis, Maryland 21401
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Annapolis, Maryland 21401
    1 / 17
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21401
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 23
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21401
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as... View all property information
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    Annapolis, Maryland 21401
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Annapolis, Maryland 21401
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    5 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please... View all property information
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    Annapolis, Maryland 21401
    1 / 24
    6 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
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    Annapolis, Maryland 21403
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Location Information
    Annapolis, Maryland 21403
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