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House Rentals and Beach Rentals in Annapolis, MD

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    Travelers to Annapolis are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    5 of 5 bubbles (3) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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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... View all property information
    Location Information
    Annapolis, Maryland 21405
    5 of 5 bubbles Reviewed October 21, 2015
    Our group of 6 couples rented this lovely home during the Annapolis, MD Annual Powerboat Show. Having stayed in hotels for prior boat shows, we wanted to have the freedom and...
    5 of 5 bubbles Reviewed September 27, 2014
    Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
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    1 / 6
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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 +... View all property information
    Location Information
    Annapolis, Maryland 21401
    5 of 5 bubbles 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...
    5 of 5 bubbles 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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    1 / 50
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | 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
    Location Information
    Annapolis, Maryland 21403
    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
    Location Information
    Annapolis, Maryland 21146
    1 / 30
    4.5 of 5 bubbles (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 21401
    4 of 5 bubbles 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 / 25
    5 of 5 bubbles (15) 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 21401
    5 of 5 bubbles Reviewed December 11, 2016
    We absolutely loved our time in this home! We were in town for the Annapolis Half Marathon. We walked to the starting line from the house, and even walked downtown and the...
    5 of 5 bubbles Reviewed November 8, 2016
    This quaint home has loads of charm and plenty of space. Convenient to all the locations that were important to us, we walked to the Navy-Marine Corp Memorial Stadium and only had...
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    1 / 26
    3 of 5 bubbles (1) Average
    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
    Location Information
    Annapolis, Maryland 21403
    3 of 5 bubbles Reviewed September 27, 2016
    Location quiet with good views.Disappointed that house was advertised with hot tub which was one of the main reasons this home was selected, and there was no hot tub. Owner said...
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    1 / 26
    5 Bedrooms, 3 Bathrooms, Sleeps 20 | Quick View
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    • Waterfront
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    • Ocean Views
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    About this property
    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden... View all property information
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    Annapolis, Maryland 21403
    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
    Location Information
    Annapolis, Maryland 21403
    1 / 20
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
    About this property
    A Charming detached one-family home located in one of the most vibrant neighborhoods of Annapolis. Perfectly located in a quiet residential street, only 0.8 miles from the United States Naval Academy and a short walk from Main street. The home is situated only a few steps away from West street and... View all property information
    Location Information
    Annapolis, Maryland 21401
    5 of 5 bubbles Reviewed December 3, 2016
    My two friends and I wanted a place to get away close to our homes in PA and we found it. Annapolis provided everything we were looking for and the house was beautiful and...
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    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
    Location Information
    Annapolis, Maryland 21409
    1 / 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    • Central Heating
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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
    Location Information
    Annapolis, Maryland 21401
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Waterfront
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    • x
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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
    Location Information
    Annapolis, Maryland 21032
    1 / 40
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    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
    Location Information
    Annapolis, Maryland 21403
    1 / 64
    6 Bedrooms, 6 Bathrooms, Sleeps 15 | Quick View
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    • ?
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    • x
    About this property
    The Yellow House is a Gorgeous /charming Large Southern Colonial ( featured in 2 magazines) with its large welcoming front porch and multiple decks off the back, and is situated on one of the most picturesque and serene creeks in Annapolis. Historic Annapolis, one of the most beautiful little... View all property information
    Location Information
    Annapolis, Maryland 21403
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Annapolis, Maryland 21403
    1 / 23
    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... View all property information
    Location Information
    Annapolis, Maryland 21401
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    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    Annapolis, Maryland 21403
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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    • x
    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home & property. Cut and paste the following link: AnnapolisWaterfrontRentals..om This incredible home has 100' of floor-to-ceiling windows nestled in the tree canopy for... View all property information
    Location Information
    Annapolis, Maryland 21401
    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
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    Annapolis, Maryland 21401
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 21
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 22
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Annapolis, Maryland 21401
    1 / 20
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Annapolis, Maryland 21401
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Annapolis, Maryland 21401
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Annapolis, Maryland 21403
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Annapolis, Maryland 21401
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21409
    1 / 23
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Annapolis, Maryland 21409
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    Annapolis, Maryland 21409
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Annapolis, Maryland 21403
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
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    Annapolis, Maryland 21403
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Annapolis, Maryland 21401
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Grill
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    • Wi-Fi
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Annapolis, Maryland 21401
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Grill
    • Washer
    • Internet Access
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Annapolis, Maryland 21401
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    Location Information
    Annapolis, Maryland 21409
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