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Holiday Rentals near Annapolis Historic District

Main Street, Annapolis, Maryland 21401
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    Travellers to Annapolis are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 107 Rentals in Annapolis
    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 26
    (22)Excellent
    1.9 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Excellent Location in Downtown Annapolis- walk to everything !1 / 17
    (1)Excellent
    0.4 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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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    Pet friendly
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    Smoking allowed
    Reviewed 21 June 2015
    Owner has everything imaginable in the home that you would ever need for a vacation getaway. The house has lots of room so you have your privacy when needed. Beautiful...
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    About this property
    Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    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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    Reviewed 20 August 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
    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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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    0.9 kilometres from Annapolis Historic District
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,...
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    Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    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
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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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    • Private Garden
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    Pet friendly
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    Smoking allowed
    Reviewed 18 June 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 Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    0.1 kilometres from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
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    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Charming waterfront home located in Downtown Historic Annapolis1 / 31
    (15)Very good
    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
    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
    (5)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
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    Renovated Historic Home located downtown with parking - Walk everywhere !1 / 22
    (177)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
    (52)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
    (67)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
    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
    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
    Charming garden row home, easy 4 block walk to the heart of Annapolis.1 / 14
    (38)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
    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
    Beautiful Condo - Water View Near City Dock1 / 25
    (77)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
    (15)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
    (5)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
    (98)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
    (15)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
    Upscale home in Eastport / Annapolis1 / 24
    (5)Excellent
    1.2 kilometres from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
    Two Blocks to Town, Underground Parking Garage1 / 25
    (71)Excellent
    0.5 kilometres from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Location Information
    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
    (74)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
    (27)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
    (5)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
    (14)Excellent
    0.3 kilometres from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Location Information
    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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    • Patio
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    Location Information
    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Waterfront Oasis in Eastport - Walk to Downtown and USNA1 / 41
    (32)Excellent
    0.9 kilometres from Annapolis Historic District
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Location Information
    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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    Location Information
    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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    Location Information
    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    1
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