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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
    0.2 kilometres from Annapolis Historic District
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    0.1 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 4 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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    0.1 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Named after the owner’s great-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...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    0.2 kilometres from Annapolis Historic District
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars on-site. Located on a quiet residential street just 2 blocks from Main Street, the home has 2 bedrooms and 2 full baths on the 2nd floor, and 2 more bedrooms on the 3rd floor....
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    0.1 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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 neighboring townhouses on the block. As part of the larger City...
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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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    • Washer
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    • Terrace
    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 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
    0.3 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This unit has all new furniture, bedding and housewares. Unit is directly across from Gate 2 at the Naval Academy so a block in either direction and you can get onto the Yard. You'll be a short 1 block walk to Ego Alley and all of the restaurants, shops and water taxi. Eastport is a 15 minute walk....
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Charming Charles Retreat1 / 25
    (1)Excellent
    0.3 kilometres from Annapolis Historic District
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    Reviewed 21 October 2023
    Perfect Location- walkable to Main Street and West Street, the Naval Academy! Such a charming neighborhood with historic homes and tree lined streets. Very safe. The home is...
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    About this property
    Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history and vibrant culture of this charming city. Our home offers unparalleled comfort and style, featuring modern amenities, cozy rooms, and tasteful décor. Step outside & find yourself in the...
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    0.3 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 enough, the outdoors are a rare gem in the city: a...
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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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    Pet friendly
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    Smoking allowed
    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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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 the most stunning decorative fireplace dating back...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    0.1 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the Annapolis waterfront, the State Capitol, restaurants, shopping and the Naval Academy, this cherished property is registered with the Historical Society of Annapolis (originally...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.1 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Balcony
    • Patio
    • Air Conditioning
    • Grill
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This well-appointed recently-renovated home in the heart of Annapolis is located just steps from both the Capitol and City Dock. Guests will enjoy the new upgrades, including the open floor plan, gourmet kitchen and new baths. The private backyard is great for those who are looking to entertain...
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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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