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Holiday Rentals near Annapolis Historic District

Main Street, Annapolis, Maryland 21401
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    Travellers to Annapolis are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 17 Rentals in Annapolis
    Stunning Home in the Heart of Downtown Annapolis1 / 18
    (1)Excellent
    0.4 kilometres from Annapolis Historic District
    3 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    0.2 kilometres from Annapolis Historic District
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    0.1 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    *Parking Passes available on request; first come/first serve. Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose as a Horse Barn and later became a popular hotel, due to its location in the center of the City, along with the...
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    About this property
    The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 4+ cars! Built in 1880, The Randall House, with its 4 bedroom and 4 Baths, is located just steps from the USNA Gate 1, downtown shops, restaurants & City Dock. Designed around entertaining, guests will be...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    0.2 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    The gorgeous Downtown Annapolis home was meticulously remodeled from top-to-bottom in a luxurious fashion. This fully-renovated 1800 historic home is a few blocks from Main Street, the Annapolis Waterfront, a public water pier at the end of the street, and the Naval Academy - perfect for Navy...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    0.2 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    *Flexible Commissioning Week Cancellation Policy* Large Historic Downtown Annapolis gorgeous home with 2 parking spaces! With all the charm of an old world house, the professionally re-decorated home has all of the contemporary amenities for guests looking to experience a 5-Star luxury stay....
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    0.4 kilometres from Annapolis Historic District
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Terrace
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    About this property
    *Flexible Commissioning Week Cancellation Policy* The charming Harborview Terrace is located just a few houses away from the water in Downtown Annapolis just a quick walk to shops, restaurants, the waterfront and the Naval Academy. The newly-decorated 3 bedrooms and 2.5 baths is plenty of space...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    0.1 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    Named after the owner’s grandfather, who was instrumental in building both Annapolis and Academy fire departments, the historic home built in 1885, is a quintessential-Annapolis charmer. And what makes it even more charming is the full gut renovation that was just completed. From the bright new...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    0.3 kilometres from Annapolis Historic District
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    About this property
    **Ask us about weekday stays with no minimum-stay requirements! Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars. Owned by 4 Naval Academy graduates - 3 U.S. Marines and one Navy nuclear surface warfare officer -...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    0.1 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy the historic charm of this Annapolis home built in 1920, owned by a Navy family, just walking distance from Main Street, with all the bells and whistles of a full renovation. The kitchens and baths have all new stainless-steel appliances and fixtures to complement the high ceilings and...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.3 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Flexible Commissioning Week Cancellation Policy* Welcome to this gorgeous Texas-themed downtown Annapolis home. Every inch of this home has custom finishes and has been painstakingly renovated by the gracious homeowner who recently opened his home to guests. And if the interior of the home isn't...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    0.2 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Located in the heart of Annapolis' Historic District sits this 1 bedroom, 1.5 bath cozy apartment. A mere stone's throw from the Naval Academy Gate 1, this apartment boasts hardwood floors, granite countertops, stainless still appliances, and washer & dryer. Location is convenient to downtown...
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    *Flexible Commissioning Week Cancellation Policy* When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s USNA alma mater. What they found with this special home is so much more! This historic home's family room off the kitchen has...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    0.1 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
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    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Parking Passes available on request; first come/first serve. This beautiful sunny home is located on a quiet tree-lined street in downtown Annapolis, just an easy walk to all the shops, restaurants, waterfront and Naval Academy. The house has been updated with all new furniture and finishes,...
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.4 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *A dedicated parking spot at a nearby garage is provided. Please contact us for details. Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovated late 1800s charmer with touches of historical elegance. On the first level, relax...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.2 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Flexible Commissioning Week Cancellation Policy* This Annapolis home, located directly across the street from Naval Academy's Gate 1, is also a moving tribute to the owner's heroic brother, 1st Lt Travis Manion. An experienced war veteran, Manion was fatally wounded by an enemy sniper while...
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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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