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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.
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Perfect for Corporate rental, rolocation or families displaced by fire, flood or other damage. Conveniently located to Rte 50 and Historic Downtown Annapolis. Walking distance to grocery, pharmacy, package goods, coffee shops, restaurants, walk/run/bike path. 1/8 mile from Rte 50 and 1 mile... View all property information
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    Annapolis, Maryland 21401
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    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Waterfront
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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 & property on-line at the on-line link: AnnapolisWaterfrontRentals 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
    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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    4.5 of 5 stars (3) Very good
    4 Bedrooms, 2 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. We have taken great care and paid pain-staking... View all property information
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    Annapolis, Maryland 21401
    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...
    4 of 5 stars Reviewed November 5, 2013
    The house worked out great for 3 couples and one 3 year old. The 3 year old loved having his own room with a great selection of books and toys. Everyone else enjoed the feel of...
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    1 / 21
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    NO SAILING EXPERIENCE NECESSARY! Use our yacht as a large 4 bedroom floating villa. This 42' Lagoon cat is the way to spend a vacation on the water. Each stateroom has a queen size bed, skylights, full bath, and loads of room for storage. Our friendly crew will help you get to know the boat and... View all property information
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    Annapolis, Maryland 21401
    5 of 5 stars Reviewed December 29, 2015
    I was on Heaven for two nights with a group of friends and had the best time. It was very clean and comfortable. What a unique experience compared to staying in a hotel. With...
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    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 21401
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    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
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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. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
    Location Information
    Annapolis, Maryland 21401
    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 Bedroom, 1 Bathroom, Sleeps 2 | 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!  ... View all property information
    Location Information
    Annapolis, Maryland 21403
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. The security guard at the booth... View all property information
    Location Information
    Annapolis, Maryland 21403
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    5 of 5 stars (3) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 13 | 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 stars 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 stars 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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    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    Location Information
    Annapolis, Maryland 21403
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
    • Balcony
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    • Pet-friendly
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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... View all property information
    Location Information
    Annapolis, Maryland 21403
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
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    • Porch
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    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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
    5 Bedrooms, 3 Bathrooms, Sleeps 20 | Quick View
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    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Internet Access
    • Washer
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
    • x
    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
    Location Information
    Annapolis, Maryland 21403
    1 / 25
    5 of 5 stars (7) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
    Location Information
    Annapolis, Maryland 21401
    5 of 5 stars Reviewed November 9, 2015
    Location permits walking to the USN Academy stadium and many other areas of interest. Bed was most comfortable, coffee and water and snacks provided and owner Was available...
    5 of 5 stars Reviewed October 13, 2015
    We absolutely loved this Beautiful Cottage! Very clean, well maintained and exactly as advertised. The Owner was very friendly and available to assist if we needed anything. Two...
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    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... View all property information
    Location Information
    Annapolis, Maryland 21401
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