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Vacation Rentals and Condos in Annapolis, MD

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    All 22 Rentals in Annapolis
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    Travelers to Annapolis are booking August dates now. Secure your vacation rental today, and have the perfect trip.
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    $350
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    1 / 25
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
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    $800
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    1 / 31
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
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    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
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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
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Washer
    • Stereo System
    • Dryer
    • Satellite TV
    • Fireplace
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    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...
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    $300
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    1 / 9
    1 Bedroom / 1 Bathroom / Sleeps 2
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    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
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    Location Information
    Annapolis, Maryland 21401
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    $750
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    1 / 26
    5 of 5 stars (2) Excellent
    6 Bedrooms / 4 Bathrooms / Sleeps 13
    travelers have booked this property
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    Amenities & Details
    • 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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    $400
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    1 / 22
    5 of 5 stars (1) Excellent
    3 Bedrooms / 6 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    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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    Annapolis, Maryland 21409
    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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    $200
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    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
    From
    $450
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    1 / 7
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • 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
    From
    $595
    / Night
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    1 / 26
    5 Bedrooms / 3 Bathrooms / Sleeps 20
    Overview Make Inquiry
    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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    $450
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Porch
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The house, built in 1878 by oyster packer Josiah Russell, has been owned by Campbell family members for at least four generations.On carpet, an elegant prayer rug is hung as a tapestry on a wall in the dining area. Chinese porcelain, cherished and collected by Jane and her parents, are displayed on... View all property information
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    Location Information
    Annapolis, Maryland 21401
    From
    $450
    / Night
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Make Inquiry
    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
    $325
    / Night
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    1 / 6
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    $350
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    1 / 25
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    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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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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 / 12
    1 Bedroom / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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
    $600
    / Night
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    1 / 14
    1 Bedroom / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Watersports Nearby
    • Ocean Views
    • Water Views
    • Swingset
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • 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. With access to the beach to the... 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
    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
    $321
    / Night
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Deck
    • Air Conditioning
    • Satellite TV
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    2,700 Sq. Ft. Of Casual Waterfront Elegance 50' From The Chesapeake Bay ! 2,700 sq. ft. of casual waterfront elegance 50' from the shores of the Chesapeake bay and 15 minutes from historic downtown Annapolis and the Naval Academy... You will be so close to the Chesapeake Bay that your view from... View all property information
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    Location Information
    Annapolis, Maryland
    From
    $595
    / Night
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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    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
    $450
    / Night
    View Details
    1 / 13
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    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