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Vacation Rentals nearby Annapolis Historic District

Main Street, Annapolis, Maryland 21401
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    Travellers to Annapolis are booking August dates now. Secure your vacation rental today, and have the perfect trip.
    All 103 Rentals in Annapolis
    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    1.6 kilometres from Annapolis Historic District
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    1.1 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    5BR Annapolis Family Home1 / 42
    (1)Excellent
    3.1 kilometres from Annapolis Historic District
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    1.1 kilometres from Annapolis Historic District
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We stayed at the cottage for an extended period of time and it was very enjoyable. The house itself was well put together and had everything that we could have needed. The...
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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, brewery, sailing, kayaking & more. We have everything here in Annapolis - USNA, sailing, culture,...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    1.3 kilometres from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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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...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.2 kilometres from Annapolis Historic District
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Our home is centrally situated within the heart of the Historic District. You'll be only ~two blocks from Academy Gate Three, City Dock, St John's College, Main Street food, PACA House weddings and the Maryland state Capital. This is a Federal style, 1870's three-story row home which was partially...
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    0.4 kilometres from Annapolis Historic District
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Ideally located in the heart of Annapolis's Historic and Art Districts and now including PARKING!!. Fully updated detached home with historic charm and an inviting front porch. Recently renovated to include granite countertops and stainless steel appliances. Enclosed rear yard provides an...
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    Annapolis, Maryland
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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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    • Private Garden
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    Pet friendly
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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
    Charming waterfront home located in Downtown Historic Annapolis1 / 31
    (21)Excellent
    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 / 15
    (7)Very good
    0.9 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
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    Legislative Session 2021 is Available.1 / 23
    (10)Excellent
    0.4 kilometres 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
    0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!1 / 28
    (11)Very good
    4.9 kilometres from Annapolis Historic District
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
    “Athens of America,” Annapolis Apartment Two B1 / 12
    (6)Very good
    0.9 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
    Jode's Retreat' Your Home Away From Home1 / 21
    (10)Very good
    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
    Historic beach Cottage1 / 29
    (13)Excellent
    4.1 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Impeccable, near Navy Stadium1 / 22
    (63)Excellent
    2.4 kilometres from Annapolis Historic District
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Renovated Historic Home located downtown with parking - Walk everywhere !1 / 22
    (181)Excellent
    0.3 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Location Location Location!!!50 Steps from Main Street and all of the action1 / 30
    (54)Excellent
    0.1 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown1 / 35
    (70)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
    0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!1 / 29
    (19)Excellent
    0.2 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
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    Historic Grandeur in the Heart of Downtown1 / 39
    (5)Excellent
    0.1 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
    Magical Memories - Annapolis Chesapeake Bay Waterfront Home w/Pool.1 / 41
    (28)Excellent
    4.1 kilometres from Annapolis Historic District
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Charming garden row home, easy 4 block walk to the heart of Annapolis.1 / 14
    (44)Excellent
    0.4 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Yellow Cottage on Harness Creek1 / 10
    (70)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 / 25
    (81)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
    Views! Charming Renovated Beachfront House in Bay Ridge Annapolis. 10 min dwntwn1 / 26
    (21)Excellent
    4.6 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
    Pristine Renovation: Perfect Downtown  Location walk to the Academy or Stadium!1 / 33
    (45)Excellent
    1.4 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
    Cozy Cottage by the Beach1 / 25
    (21)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
    Casual Coastal Living in Historic Eastport/Annapolis1 / 50
    (9)Excellent
    1.0 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
    Annapolis waterfront 'tiny house' in garden setting1 / 19
    (112)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
    Eastport Cottage with Waterview  - Minutes from Downtown Annapolis and USNA1 / 8
    (19)Excellent
    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
    Waterside with it All! Private Pier, Hot Tub and Pool.1 / 50
    (9)Excellent
    4.3 kilometres from Annapolis Historic District
    6 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 18
    Private 2 BR Apt -- Less than 1 mi to Downtown & USNA gate1 / 24
    (12)Excellent
    1.2 kilometres 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
    Two Blocks to Town, Underground Parking Garage1 / 25
    (75)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
    (26)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
    (79)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 / 12
    (1)Very good
    0.9 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
    The Cottage on Spa Creek1 / 36
    (30)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
    Retreat for Four in Eastport, Steps away from Restaurant Row & Downtown1 / 18
    (6)Excellent
    0.8 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
    Extended Stays Available Please contact for Availability and Pricing.1 / 18
    (15)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
    Sleeps 10! Great Reviews.1 / 36
    (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 / 41
    (34)Excellent
    0.9 kilometres from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
    WALK TO THE STADIUM!  Gorgeous, newly built 5 bedroom home.1 / 27
    (3)Excellent
    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 / 35
    (9)Excellent
    0.2 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 / 20
    (10)Very good
    0.9 kilometres 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
    The Kings Court - Downtown 4 BR Gem, One Block to the Naval Academy Gates!1 / 38
    (5)Excellent
    0.3 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
    0198 Days Landing. Your Chesapeake Family Getaway! Lake, Pool, Hot Tub, Dock.1 / 50
    (7)Excellent
    4.5 kilometres from Annapolis Historic District
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport1 / 28
    (48)Excellent
    0.7 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    0146 BLUE ANGELS NEST - Downtown Annapolis. Green Outdoor Space!1 / 35
    (6)Excellent
    0.1 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
    Extended Stays Available Please contact for Availability and Pricing.1 / 18
    (39)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
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