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Vacation Rentals and Condos in Annapolis, MD

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    $350
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    1 / 25
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    $425
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    1 / 30
    4.5 of 5 stars (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9
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    $300
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Satellite TV
    • Fireplace
    • DVD Player
    • Housekeeping...
    • Deck
    • Wi-Fi
    • Stereo System
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks... View all property information
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    Location Information
    Annapolis, Maryland 21403
    5 of 5 stars Reviewed July 15, 2014
    If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to...
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    1 / 28
    5 of 5 stars (2) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 13
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    • Game Room
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Deck
    • Pool Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
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    Location Information
    Annapolis, Maryland 21405
    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...
    5 of 5 stars Reviewed August 11, 2014
    We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large...
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    $450
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    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Make Inquiry
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    • Washer
    • Water Views
    • Central Heating
    • Internet Access
    • Fireplace
    • Stereo System
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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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    Location Information
    Annapolis, Maryland 21401
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    $179
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    1 / 4
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • DVD Player
    • Refrigerator
    • Internet Access
    • Dryer
    • Air Conditioning
    • Satellite TV
    • Washer
    • Playground
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has twin beds. Large loft has queen size bed. Although the condo can accommodate 6 for sleeping, I will rent only to parties of 4 or fewer. Dining room can seat 8 + Washer and Dryer,... View all property information
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    Location Information
    Annapolis, Maryland 21401
    5 of 5 stars 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 stars 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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    $225
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    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Washer
    • Internet Access
    • Watersports Nearby
    • DVD Player
    • Air Conditioning
    • Deck
    • Water Park Nearby
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue... View all property information
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    Location Information
    Annapolis, Maryland 21403
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    $400
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    1 / 22
    5 of 5 stars (2) Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 10
    other traveler has booked this property
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Water Views
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • TV
    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Annapolis, Maryland 21409
    5 of 5 stars Reviewed June 30, 2015
    This was one of the best, if not the best, place we have ever stayed. It is very comfortable with high quality furniture and linens and it is set in an idyllic wooded grove on a...
    5 of 5 stars Reviewed April 9, 2015
    The home was located at a very continent location just 5-10mins drive to Naval academy and Annapolis downtown. The home was clean and have all the amenities. The water views from...
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    From
    $595
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    5 Bedrooms, 3 Bathrooms, Sleeps 20
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Playground
    • Shared Tennis Court
    • Hot Tub
    • Internet Access
    • Watersports Nearby
    • Air Conditioning
    • Private Fishing...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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
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    Location Information
    Annapolis, Maryland 21403
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    From
    $325
    / Night
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    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
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    Location Information
    Annapolis, Maryland 21403
    From
    $450
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    2 Bedrooms, 2 Bathrooms, Sleeps 10
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Hot Tub
    • Water Views
    • Staffed Property
    • DVD Player
    • Satellite TV
    • Housekeeping...
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen beds - 1 pull-out queen sleeper - 2 twins Unique Features - Walking distance to Naval Academy, downtown, shopping, restaurants and marinas - Shower for two - Off street parking for six -... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    $350
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    1 / 25
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Fireplace
    • TV
    • Porch
    • Wi-Fi
    • Grill
    • Watersports Nearby
    • Air Conditioning
    • Housekeeping...
    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
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    Location Information
    Annapolis, Maryland 21401
    5 of 5 stars Reviewed April 23, 2015
    beautiful cottage in a perfect location. 5 min walk to the Navy Stadium. 10 min walk to the historic downtown area where there are many specialty shops, restaurants, taverns and...
    5 of 5 stars Reviewed April 15, 2015
    I've used the "cottage" a few times on recommendation of a friend as I do business often in Annapolis and have found it to be convenient, comfortable and well cared for. With its...
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    From
    $375
    / Night
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    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Refrigerator
    • TV
    • Deck
    • DVD Player
    • Dryer
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    Location Information
    Annapolis, Maryland 21403
    From
    $650
    / Night
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    1 Bedroom, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Balcony
    • Terrace
    • Garage
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    Location Information
    Annapolis, Maryland 21403
    From
    $250
    / Night
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    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Water Views
    • Waterfront
    • Air Conditioning
    • Boat Available
    • DVD Player
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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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    Location Information
    Annapolis, Maryland 21409
    From
    $595
    / Night
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    • Dryer
    • Internet Access
    • Waterfront
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Make Inquiry
    Location Information
    Annapolis, Maryland
    From
    $400
    / Night
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    1 / 13
    4 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Internet Access
    • Dryer
    • DVD Player
    • Washer
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac... View all property information
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    Location Information
    Annapolis, Maryland 21403
    From
    $850
    / Night
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    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 14
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Stereo System
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
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    Location Information
    Annapolis, Maryland 21401