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Holiday Rentals near Annapolis Historic District

Main Street, Annapolis, Maryland 21401
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    Travellers to Annapolis are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 121 Rentals in Annapolis
    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 26
    (22)Excellent
    1.2 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4.4 miles from Annapolis Historic District
    5 Bedrooms, 3 Bathrooms, Sleeps 21 Quick View
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    Excellent Location in Downtown Annapolis- walk to everything !1 / 17
    (1)Excellent
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    1.0 miles from Annapolis Historic District
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed 17 September 2018
    Great house, lots of space everything you want, nice small touches. Owner is very responsive to questions and very friendly. Highly recommended and we would use it again.
    Reviewed 18 May 2018
    Home had lots of rooms in various configurations which were great for our multi-generational family visit. Even toys for the toddlers! Host super helpful, even found us a...
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    About this property
    The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms...
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    Annapolis, Maryland
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    2nd floor apartment steps from Naval Academy in the heart of downtown Annapolis1 / 24
    (2)Excellent
    0.4 miles from Annapolis Historic District
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    0.7 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    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
    0.7 miles from Annapolis Historic District
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 19 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, sailing, kayaking and 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
    Annapolis waterfront dream1 / 30
    (1)Excellent
    1.1 miles 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
    5BR Annapolis Family Home1 / 42
    (1)Excellent
    1.9 miles 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
    Bay Ridge Seaglass Home by the Chesapeake Bay1 / 20
    (1)Excellent
    3.1 miles from Annapolis Historic District
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.6 miles 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
    0.7 miles from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    0.6 miles from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    4.2 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters of the Chesapeake Bay. Water views from almost every room. Features 4 bedrooms and 4 bathrooms with luxury upgrades, viking and KitchenAid appliances, comfortable leather couches...
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    4.8 miles from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as...
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    Annapolis, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.8 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    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
    2.9 miles 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
    2.3 miles 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
    2.6 miles from Annapolis Historic District
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
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    Annapolis, Maryland
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    0.8 miles 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
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    0.7 miles 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
    0.1 miles 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
    5.7 miles 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
    0.2 miles 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
    0.2 miles from Annapolis Historic District
    3 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Reviewed 17 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
    3.2 miles from Annapolis Historic District
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    All the best of Annapolis awaits at this vacation rental house, set 10 minutes from downtown and only 1 block from Chesapeake Bay! Comfortably hosting 6, this sweet spot offers 3 bedrooms, 2 full baths, 2 half baths, a flagstone patio and screened porch. Watch an Annapolis Boat Show, visit the...
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    Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    0.0 miles from Annapolis Historic District
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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
    Refinished W/Best Backyard In Annapolis, Minutes From Downtown & Naval Academy1 / 25
    (18)Excellent
    1.5 miles 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
    Charming waterfront home located in Downtown Historic Annapolis1 / 31
    (6)Excellent
    0.4 miles 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
    “Athens of America,” Annapolis Apartment One B1 / 15
    (6)Very good
    0.6 miles 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 / 23
    (9)Excellent
    0.3 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
    0025 Bella Chateau. SPECIAL Commissioning Week 2021 Discount! Ask!1 / 27
    (10)Very good
    3.0 miles 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
    We Get Repeat Renters!!1 / 40
    (40)Excellent
    0.6 miles 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
    DISCONTINUING SHORT TERM RENTALS AS OF AUGUST 1, 20201 / 50
    (17)Excellent
    0.1 miles from Annapolis Historic District
    7 Bedrooms, 8 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 10
    “Athens of America,” Annapolis Apartment Two B1 / 12
    (3)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
    Gorgeous Luxury Home steps to USNA/State House/City Dock1 / 14
    (23)Excellent
    0.2 miles 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
    Jode's Retreat' Your Home Away From Home1 / 21
    (5)Very good
    1.0 miles 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
    Clean & Spacious Reserve Home or Individual room1 / 20
    (14)Excellent
    4.5 miles from Annapolis Historic District
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Historic beach Cottage1 / 29
    (8)Excellent
    2.5 miles 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
    Beautiful Home 2 Blocks From Navy Stadium!1 / 20
    (2)Excellent
    1.2 miles 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
    Upscale home with parking for 4 cars in driveway.  Walk to downtown.1 / 21
    (74)Excellent
    0.5 miles 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
    Renovated Historic Home located downtown with parking - Walk everywhere !1 / 22
    (158)Excellent
    0.2 miles 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
    Annapolis Downtown 4BR - 0045 The Bassford House - Gorgeous!1 / 50
    (2)Excellent
    0.0 miles 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
    Location Location Location!!!50 Steps from Main Street and all of the action1 / 30
    (43)Excellent
    0.1 miles 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
    4.5 miles 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
    Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown1 / 35
    (65)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
    0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!1 / 29
    (14)Excellent
    0.1 miles from Annapolis Historic District
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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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 miles 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
    Charming garden row home, easy 4 block walk to the heart of Annapolis.1 / 14
    (28)Excellent
    0.2 miles 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
    (26)Excellent
    2.5 miles 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
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