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House Rentals and Beach Rentals in Annapolis, MD

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    Travelers to Annapolis are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 24
    5 of 5 stars (3) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    1 / 25
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 6
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 10
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Fully renovated to perfection! Contractor owned home renovated floor to ceiling. Tall trees, water access, and a quaint and quiet neighborhood! 5-7 minutes from downtown/USNA/etc. Open concept main floor, perfect for large groups. We recently had a 25 person baby shower downstairs and easily fit... View all property information
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    Annapolis, Maryland
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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... View all property information
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    Annapolis, Maryland
    1 / 26
    3 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Come stay in this beautiful 3-bedroom, 3.5-bathroom single-family home on Oyster Creek – You’ll be able to enjoy fantastic views of the Chesapeake Bay from almost every single room! There’s enough room for 9 guests to comfortably sleep here, so it’s a great size for a family retreat. The... View all property information
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    Annapolis, Maryland
    1 / 30
    4.5 of 5 stars (3) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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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... View all property information
    Location Information
    Annapolis, Maryland
    4 of 5 stars 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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    1 / 15
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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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... View all property information
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    Annapolis, Maryland
    1 / 25
    5 of 5 stars (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Annapolis, Maryland
    5 of 5 stars Reviewed September 22, 2015
    We were there for 2/C midshipmen Parent Weekend, and we loved it. It felt like home, it was very cozy, we could all do our own thing or be together. We went to a Navy football...
    5 of 5 stars Reviewed July 6, 2015
    I came down with a group of friends for a birthday weekend. This house could not have been more perfect! Beautiful decorations, fun upstair loft/bedroom, comfy accommodations, it...
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    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay in and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former " Home of the Week" it is also one of the most photographed homes downtown. ( Oct... View all property information
    Location Information
    Annapolis, Maryland
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    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Waterfront Property (built in 2000) minutes outside Annapolis, Maryland. Expansive views of the river from this gated custom built home (2176 sq ft excluding basement) with 278' pier on private lot with your own 50' sandy beach. This comfortable home boasts 3-4 bedrooms (and Murphy bed in the... View all property information
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    Annapolis, Maryland
    1 / 23
    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... View all property information
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    Annapolis, Maryland
    1 / 50
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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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,... View all property information
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    Annapolis, Maryland
    1 / 10
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Our home is a 5 bedroom quality built home. This room is an office converted in to an extra bedroom space for guests to enjoy. It is located on the main level just inside the main entrance. It had double french doors which lock for privacy. Its a clean and cozy space and an expensive way to travel.... View all property information
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    Annapolis, Maryland
    1 / 7
    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... View all property information
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    Annapolis, Maryland
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    HOUSE<BR>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... View all property information
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    Annapolis, Maryland
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    *** 20% Off Summer Rates!! Was $162, now $129 *** 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... View all property information
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    Annapolis, Maryland
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Waterfront
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    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped. View all property information
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    Annapolis, Maryland
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    A unique apartment , private entrance,private off street parking. 5 minute walk to city dock, close to many restaurants, bank, convenience store,nightlife,cafes, bakery. Professionally decorated to make a lovely ,comfortable space .Bose cd players in every room. Gourmet kitchen with Continental... View all property information
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    Annapolis, Maryland
    1 / 7
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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... View all property information
    Location Information
    Annapolis, Maryland
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    1 / 21
    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... View all property information
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    Annapolis, Maryland
    1 / 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay... View all property information
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    Annapolis, Maryland
    1 / 5
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
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    PROTECTED WATERS, GREAT ANCHORAGES... …gorgeous natural scenery, unique towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. Historic Annapolis, the crown jewel of the Mid-Atlantic, is the best sailing destination on the East... View all property information
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    Annapolis, Maryland
    1 / 40
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    The Yellow House is a magnificent Waterfront Property, with interior and exterior appointments, that are truly outstanding- With its magazine worthy gardens, and spacious 6 bedrooms, designed and furnished with the highest level of comfort, and relaxation. For over 9 years now we have been... View all property information
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    Annapolis, Maryland
    1 / 32
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Ref # 373878 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Our spacious home is 1.5 miles from downtown and a little over 1 mile to Navy Stadium.... View all property information
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    Annapolis, Maryland
    1 / 6
    2 Bedrooms, Sleeps 1 | Quick View
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    About this property
    Charming and beautifully appointed two bedroom, one bath historical home in Annapolis. It has a beautiful backyard with charcoal grill and deck, convenient street parking, bus shuttle one block away, also walking distance to Navel Academy Stadium and downtown Annapolis. Live like a real... View all property information
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    Annapolis, Maryland
    1 / 24
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
    • Hot Tub
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    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home and property: https://youtu.be/FBqOhPJZ-qU This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek.... View all property information
    Location Information
    Annapolis, Maryland
    4 of 5 stars Reviewed October 20, 2015
    Myself and five coworkers rented this house for a meeting. As we are from different areas across the country we usually meet at hotels. I thought we would try something different...
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of... View all property information
    Location Information
    Annapolis, Maryland