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Annapolis Vacation Rentals

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    Travelers to Annapolis are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 98 Rentals in Annapolis
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Charming and Spacious Annapolis Victorian1 / 24
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Charming Home close to historic district1 / 29
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Location, location, location! Literally walk out the front door to the hustle and bustle of downtown Annapolis with the City Dock just steps away. 2 blocks to Naval Academy Gate 1. Pubs, shops and cafes just steps away! Small patio for some outdoor relaxation, wifi tv, netflux, hulu and roku....
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 25
    (17)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Porch
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2017
    My family just moved here in December 2016 and we needed a place to stay for a new months. It turned into 6 months and Alka B. was a wonderful landlord and was very helpful with...
    Reviewed July 13, 2017
    The location is amazing, especially for Navy football games! Plus the owner is right next door and very responsive for any questions or needs. Very accommodating and helpful...
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    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. <BR>Sun Porch & Plenty of parking.<BR>A perfect place to relax and enjoy Annapolis, the property is available all year...
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Cozy Beach Cottage: Newly Remodeled and Family Friendly!1 / 22
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Annapolis Waterfront very near USNA1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Waterfront
    • DVD Player
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    Pet friendly
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    Reviewed April 15, 2017
    A clean, peaceful retreat with spectacular views; that is exceptionally stocked!I had no need to buy anything! At one point, I asked the owner if/or where the hand mixer was...
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    About this property
    Waterfront timber frame large cottage in Annapolis, MD. Private, wooded setting with excellent views. Please inquire to the property owner for rates and quote. This house is an energy efficient 9 year old house perched atop a small bluff overlooking picturesque Mill Creek and an...
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    Annapolis, Maryland 21409
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Refinished W/Best Backyard In Annapolis, Minutes From Downtown & Naval Academy1 / 24
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
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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 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Spacious, Modern Condo nr. Navy Stadium, downtown & Mall . Easy access route 501 / 6
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Terrace
    • Satellite TV
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    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 29, 2014
    We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
    Reviewed November 12, 2013
    My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a...
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    About this property
    Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has queen size bed. Large loft has two single beds. Although the condo can accommodate 6 for sleeping, I will generally only rent to parties of 4 or fewer. Dining room can seat 8 +...
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 50
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
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    • Housekeeping Included
    • Patio
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    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, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed June 21, 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.<BR><BR>We have taken great care and paid pain-staking...
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    5 Bedroom, 3.5 Bath, Located Near Downtown Annapolis1 / 11
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Beautiful Eastport Home, Walk to Naval Academy1 / 15
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Terrace
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    • Secure Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 16, 2016
    Beautifully decorated. Walking distance to Naval Academy. Plenty of sleeping space. Private outdoor space.
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    About this property
    Walk to the city docks and naval academy in this new (2014) luxury townhouse. The king bedroom suite also has a pullout twin bed for parents with small children. Enjoy the grand piano or relax by the gas fireplace. Cookout on the sunny patio. Visit local pubs and restaurants or just walk to...
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Home ideal for USNA Induction Day, Plebe Parents Weekend, and Class Reunions1 / 24
    (1)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Smoking allowed
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    Location Information
    Annapolis, Maryland 21409
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    About this property
    A perfect home to enjoy time in Annapolis!  Located on King George Street, walking distance to the Academy or downtown, this home is open year round with a 2-night minimum stay. It is an outstanding home for Weddings, Academy Events, Alumni Gatherings or Family Vacations.  This stunningly...
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Patio
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    • DVD Player
    • Central Heating
    • Balcony
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    Pet friendly
    Kid friendly
    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 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Central Heating
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and unwind at this 2-bedroom, 1-bathroom vacation rental cottage in Annapolis. Nestled supremely within a short distance from the hustle and bustle of Maryland's capital city, this cozy cottage offers both exciting restaurants and shops, as well as numerous marine water activities at the...
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    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay when they visited and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former " Home of the Week" in the Capital Gazette it is also one of the most...
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    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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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the United States has a little something for every interest and taste, whether you're a history buff, a sports enthusiast, or someone simply looking for a peaceful retreat!   Have the...
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    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 15 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 15 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Annapolis, Maryland 21403
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Enjoy your time spent in Annapolis!1 / 22
    (18)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful Annapolis Getaway- Walk Everywhere!!!1 / 19
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful family-friendly 4-Bdr home in Murray Hill1 / 22
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Stunning home in the Historic District1 / 24
    (55)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Gorgeous Luxury Home steps to USNA/State House/City Dock-CHRISTMAS Avail bc cxl1 / 14
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lovely Eastport Artists Home/ Near Naval Academy, Marinas and Yacht Clubs1 / 24
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Large Contemporary in Wooded Privacy1 / 20
    (6)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Studio, 2 Bathrooms, Sleeps 18 Quick View
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    Annapolis, Maryland 21409
    Rental Home - 2 Bathrooms, Sleeps 18
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    Ideal for Family Get Togethers, Stadium Events, Academy Events & More1 / 17
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Summer in Murray Hill/Rent a Paddle board or Kayak on Spa Creek 2 blocks away!1 / 22
    (10)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Wonderful Eastport home - walk to downtown.  Great deck!1 / 21
    (10)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Visit Downtown Historic Annapolis And The Naval Academy1 / 21
    (30)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Heart of the Historic District!1 / 18
    (30)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Private Newly Finished Basement Apartment, 1 Mile Walk To Downtown Annapolis.1 / 16
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Historic Downtown Annapolis Home for Rent- Steps to Naval Academy1 / 17
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Annapolis Area Home With Pool! Minutes To Downtown1 / 23
    (3)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Quiet Relaxing Waterfront Swiss Chalet- Fall/Winter Weekly and Monthly Specials!1 / 24
    (28)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Annapolis, Maryland 21409
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming Historic Annapolis Home - Superior Downtown Location!!!1 / 24
    (25)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly renovated Eastport Annapolis house with water views1 / 16
    (19)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA1 / 24
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Annapolis, Maryland 21409
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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