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Vacation Rentals nearby Annapolis Historic District

Main Street, Annapolis, Maryland 21401
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    Travellers to Annapolis are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    All 361 Rentals in Annapolis
    4.2 kilometres from Annapolis Historic District
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    9.2 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    0.2 kilometres from Annapolis Historic District
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    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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    • Patio
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    Reviewed June 17, 2011
    Our family was gathering for a for a 60th Birthday Celebration and we could not have picked a better location, home, or more accommodating owner. We were trying to find a...
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    About this property
    This is an outstanding home for Alumni Weekends, Weddings, Academy Events, or Family Vacations. This beautifully appointed home offers you an at-home setting in the heart of Annapolis! The home in the downtown historic district was completely renovated and expanded in 2006. Park your cars in...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 11
    1.0 kilometres from Annapolis Historic District
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    9.0 kilometres from Annapolis Historic District
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Sophisticated Charmer with Parking & Views of the USNA Chapel Dome1 / 21
    (36)Excellent
    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Renovated Historic Home located downtown with parking - Walk everywhere !1 / 29
    (210)Excellent
    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!1 / 29
    (24)Excellent
    0.5 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4.4 kilometres from Annapolis Historic District
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Charming garden row home, easy 4 block walk to the heart of Annapolis.1 / 13
    (75)Excellent
    0.4 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Tastefully decorated Eastport Annapolis house with water views1 / 22
    (85)Excellent
    1.1 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis1 / 41
    (39)Excellent
    6.0 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Pet Friendly, walk Downtown Annapolis w/ full kitchen washer/dryer...1 / 17
    (60)Very good
    0.6 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.1 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Two Blocks to Town, Underground Parking Garage1 / 26
    (104)Excellent
    0.5 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate1 / 50
    (37)Excellent
    4.7 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Brand new Renovation in Historic District with 2 parking spots -walk everywhere1 / 21
    (111)Excellent
    1.1 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    “Athens of America,” Annapolis Apartment Two A1 / 15
    (2)Very good
    0.9 kilometres from Annapolis Historic District
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    The Cottage on Spa Creek1 / 36
    (51)Excellent
    0.8 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.2 kilometres from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 9
    THE WARDROOM - Perfectly situated for Annapolis exploration!1 / 36
    (15)Excellent
    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis1 / 22
    (18)Very good
    0.9 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport1 / 28
    (72)Excellent
    0.7 kilometres from Annapolis Historic District
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
    Extended Stays Available Please contact for Availability and Pricing.1 / 18
    (63)Excellent
    0.3 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Gorgeous renovation in HistoricDistrict -New listing !1 / 24
    (8)Excellent
    0.4 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    0.7 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    “Athens of America,” Annapolis Apartment One B1 / 19
    (8)Very good
    0.9 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    “Athens of America,” Annapolis Apartment Two B1 / 12
    (8)Very good
    0.9 kilometres from Annapolis Historic District
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Jode's Retreat "Your home away from home1 / 21
    (2)Average
    1.6 kilometres from Annapolis Historic District
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown1 / 36
    (85)Excellent
    1.0 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Historic Grandeur in the Heart of Downtown1 / 39
    (14)Excellent
    0.5 kilometres from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    The Yellow Cottage on Harness Creek1 / 10
    (99)Excellent
    4.7 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Beautiful Condo - Water View Near City Dock1 / 26
    (108)Very good
    0.7 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Annapolis waterfront "tiny house" in garden setting1 / 19
    (162)Excellent
    4.8 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate1 / 22
    (14)Excellent
    1.2 kilometres from Annapolis Historic District
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Lovely Family Home Just Minutes From Annapolis1 / 13
    (25)Excellent
    8.9 kilometres from Annapolis Historic District
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Stunning Annapolis Home! Across from the library, walk to Naval Graduation1 / 47
    (45)Excellent
    2.4 kilometres from Annapolis Historic District
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Legislative Session Available1 / 18
    (24)Excellent
    0.3 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Commissioning Week 2021 -  Sleeps 10! Great Reviews.1 / 40
    (16)Excellent
    4.9 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Waterfront Oasis in Eastport - Walk to Downtown and USNA1 / 29
    (55)Excellent
    0.9 kilometres from Annapolis Historic District
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    ACROSS FROM STADIUM - walk to downtown Annapolis.1 / 32
    (24)Excellent
    2.0 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    The Kings Court - Downtown 4 BR Gem, One Block to the Naval Academy Gates!1 / 38
    (12)Excellent
    0.6 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!1 / 35
    (17)Excellent
    0.6 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Beautiful Eastport Home walking distance to downtown and USNA. Includes parking1 / 12
    (24)Excellent
    0.8 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Hideaway in this Historic Annapolis home with parking1 / 42
    (1)Excellent
    0.4 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.0 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    3.9 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis1 / 24
    (28)Excellent
    0.3 kilometres from Annapolis Historic District
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    4.8 kilometres from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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