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Annapolis House Rentals

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    Travellers to Annapolis are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    82 Matching Rentals in AnnapolisView all 120 rentals
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    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Excellent Location in Downtown Annapolis- walk to everything !1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Charming Home close to historic district1 / 31
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis waterfront dream1 / 30
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5BR Annapolis Family Home,  Sleeps 161 / 47
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
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    About this property
    Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will love waking up to views of...
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    Annapolis, Maryland 21032
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
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    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    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, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    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 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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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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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    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 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    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 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This beautiful 3br home on the peninsula in Eastport is perfect for your Annapolis visit. It is within walking distance to popular attractions including local and national restaurants, Naval Academy, downtown Annapolis, Annapolis Yacht Club, Eastport Yacht Club, Maritime Museum, Mears Marina,...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Stunning Home in the Heart of Downtown Annapolis1 / 18
    (1)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Patio
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    Pet friendly
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    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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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 11
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Outdoor Dining Area
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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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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Clear the calendar for an easy-going getaway at this 1-bed, 1.5-bath vacation rental townhouse that sleeps 4 in Annapolis! This house boasts the best of both worlds - a tranquil atmosphere surrounding, and an ideal location just minutes from town. Spend mornings walking the nature trails,...
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    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 21401
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    About this property
    Beautiful 'Bay Ridge' has 2,900 square feet of living space and is over 100 years old. With antique furnishings, gorgeous hardwood floors, and luxurious bedrooms, you'll never want to leave this historic vacation rental home for 11 in Annapolis. The 4-bedroom 3.5-bathroom property has a pool house...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    Refinished W/Best Backyard In Annapolis, Minutes From Downtown & Naval Academy1 / 25
    (18)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Classic Victorian home in the heart of Eastport1 / 15
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Charming waterfront home located in Downtown Historic Annapolis1 / 30
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate1 / 50
    (21)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    “Athens of America,” Annapolis Apartment One B1 / 15
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0025 Bella Chateau. SPECIAL Commissioning Week 2020 Discount! Ask!1 / 27
    (10)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
    Gorgeous luxury home steps from downtown Annapolis1 / 26
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    USNA  Families & Boat Show Guests!1 / 34
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    *EVERYTHING BRAND NEW* - 7 King Beds En Suite in *HEART* of Downtown Annapolis1 / 50
    (14)Excellent
    7 Bedrooms, 8 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 10
    3 bedroom house near Navy Stadium1 / 12
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Relax on Decks in this modern 3 story townhouse, Walk to Annapolis Water Taxi.1 / 35
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Gorgeous Luxury Home steps to USNA/State House/City Dock1 / 14
    (23)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Downtown West Street Townhouse1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    The Cottage on Spa Creek1 / 36
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Secluded Waterfront Home Minutes from Down Town Annapolis1 / 11
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Clean & Spacious Reserve Home or Individual room1 / 20
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland 21409
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Walk to Navy Stadium; plenty of FREE unrestricted parking; impeccable home1 / 22
    (57)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Stunning Annapolis Home! Available 2020 USNA Commisioning Week!1 / 46
    (40)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Beautiful Home 2 Blocks From Navy Stadium!1 / 20
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Retreat for Four in Eastport, Steps away from Restaurant Row & Downtown1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Renovated Historic Home located downtown with parking - Walk everywhere !1 / 22
    (153)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Annapolis Downtown 4BR - 0045 The Bassford House - Gorgeous!1 / 50
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Historic home steps to the State House CW available1 / 22
    (13)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    LUXURY DOWNTOWN HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!1 / 37
    (150)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Location Location Location!!!50 Steps from Main Street and all of the action1 / 30
    (41)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Sleeps 10! Great Reviews.1 / 29
    (16)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    1
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