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Vacation Rentals near Annapolis Historic District

Main Street, Annapolis, Maryland 21401
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    Travelers to Annapolis are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 379 Rentals in Annapolis
    2.6 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    0.1 miles from Annapolis Historic District
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    We Get Repeat Renters!!1 / 30
    (40)Excellent
    0.6 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    USNA  Families & Boat Show Guests!1 / 30
    (9)Excellent
    5.6 miles from Annapolis Historic District
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Annapolis, Maryland
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Sophisticated Charmer with Parking & Views of the USNA Chapel Dome1 / 22
    (36)Excellent
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.5 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Renovated Historic Home located downtown with parking - Walk everywhere !1 / 30
    (210)Excellent
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Location Location Location!!!50 Steps from Main Street and all of the action1 / 29
    (71)Excellent
    0.1 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!1 / 29
    (24)Excellent
    0.3 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Annapolis Area Home With Pool! Minutes To Downtown1 / 25
    (16)Very good
    2.7 miles from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    0.2 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Tastefully decorated Eastport Annapolis house with water views1 / 22
    (85)Excellent
    0.7 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis1 / 30
    (39)Excellent
    3.7 miles from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Great Location! Walk to Downtown Annapolis, w/ full kitchen washer/dryer...1 / 17
    (60)Very good
    0.3 miles 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
    Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA1 / 7
    (34)Excellent
    0.7 miles from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Annapolis, Maryland
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Two Blocks to Town, Underground Parking Garage1 / 26
    (104)Excellent
    0.3 miles from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate1 / 50
    (37)Excellent
    2.9 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Brand new Renovation in Historic District with 2 parking spots -walk everywhere1 / 21
    (113)Excellent
    0.7 miles 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 / 16
    (2)Very good
    0.6 miles 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
    The Cottage on Spa Creek1 / 29
    (52)Excellent
    0.5 miles from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Annapolis, Maryland
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    WALK TO THE STADIUM!  Gorgeous, newly built 5 bedroom home.1 / 27
    (3)Excellent
    1.4 miles from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Annapolis, Maryland
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 9
    THE WARDROOM - Perfectly situated for Annapolis exploration!1 / 36
    (15)Excellent
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis1 / 22
    (18)Very good
    0.6 miles from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport1 / 29
    (72)Excellent
    0.4 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    Extended Stays Available Please contact for Availability and Pricing.1 / 17
    (63)Excellent
    0.2 miles 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
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks1 / 29
    (35)Excellent
    0.4 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    “Athens of America,” Annapolis Apartment One B1 / 19
    (8)Very good
    0.6 miles from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    “Athens of America,” Annapolis Apartment Two B1 / 13
    (8)Very good
    0.6 miles 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
    1.0 miles from Annapolis Historic District
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown1 / 30
    (85)Excellent
    0.6 miles 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
    0.3 miles from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    The Yellow Cottage on Harness Creek1 / 10
    (99)Excellent
    2.9 miles from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Waterfront
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    Annapolis, Maryland
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Quiet Relaxing Waterfront Suisse Chalet - Winter Specials, Great Wedding Venue1 / 28
    (39)Excellent
    2.1 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Beautiful Condo - Water View Near City Dock1 / 26
    (108)Very good
    0.4 miles 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
    3.2 miles from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate1 / 22
    (14)Excellent
    0.7 miles from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Lovely Family Home Just Minutes From Annapolis1 / 14
    (25)Excellent
    5.5 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    All Things ANNAPOLIS...1 / 11
    (4)Very good
    2.4 miles from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stunning Annapolis Home! Across from the library, walk to Naval Graduation1 / 30
    (45)Excellent
    1.5 miles from Annapolis Historic District
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Legislative Session Available1 / 18
    (24)Excellent
    0.1 miles 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
    3.0 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Waterfront Oasis in Eastport - Walk to Downtown and USNA1 / 29
    (55)Excellent
    0.5 miles from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Little Magothy Riverfront Home With Pool1 / 23
    (13)Excellent
    5.5 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    ACROSS FROM STADIUM - walk to downtown Annapolis.1 / 30
    (24)Excellent
    1.2 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    The Kings Court - Downtown 4 BR Gem, One Block to the Naval Academy Gates!1 / 38
    (12)Excellent
    0.4 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!1 / 35
    (17)Excellent
    0.3 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
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    Smoking allowed
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    Location Information
    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    *Perfect spot for a Weekend Getaway or longer term rental*1 / 23
    (56)Excellent
    0.0 miles from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Terrace
    • Washer
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    • Balcony
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    Pet friendly
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    Location Information
    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Beautiful Eastport Home walking distance to downtown and USNA. Includes parking1 / 11
    (24)Excellent
    0.5 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Location Information
    Annapolis, Maryland
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Hideaway in this Historic Annapolis home with parking1 / 30
    (1)Excellent
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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