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Vacation rentals and condos in Annapolis, MD

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All 19 Rentals in Annapolis
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$750
Per Night
1 / 26
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6 Bedrooms, 5 Bathrooms, Sleeps 13
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$250
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1 / 20
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$400
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4 Bedrooms, 3 Bathrooms, Sleeps 9
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$800
Per Night
1 / 31
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3 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Grill
  • Washer
  • Fireplace
  • Refrigerator
  • Garage
  • Parking
  • Microwave
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill. Once... View all property information
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From
$150
Per Night
1 / 18
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Refrigerator
  • Parking
  • Dryer
  • VCR
  • Stove
  • Washer
  • DVD Player
  • Dishwasher
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 at St. John's 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... View all property information
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From
$280
Per Night
1 / 3
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4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Towels Provided
  • Balcony
  • Air Conditioning
  • Garden or Yard
  • Central Heating
  • Local Guides/Maps
  • Ceiling Fans
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Unique Bed and Breakfast One of the oldest residences in Annapolis with all modern amenities. Best Breakfast! Perfect for USNA and St. John's families Wonderful hosts! View all property information
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From
$170
Per Night
1 / 14
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Stove
  • Dryer
  • Refrigerator
  • Dishwasher
  • Microwave
  • Patio
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
PLEASE CONTACT US BEFORE BOOKING FOR USNA GRADUATION and BOAT SHOWS (Rates May Vary) PLEASE NOTE WE ARE NOT TAKING RESERVATIONS FOR USNA GRADUATION 2015-2016 Large 1 BR 1 BA apartment with den/study (single pull-out daybed available), large and bright living room with pull-out sofa, and three... View all property information
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From
$400
Per Night
1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 10
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
************* NEW LISTING - AVAILABLE NOW ************ SAILBOAT SHOW 2014 - $5000.00/wk POWER BOAT SHOW 2014 - $5000.00/wk CHRISTMAS 2014 - $5000.00/wk COMMISSIONING WEEK 2015 - $5000.00/wk Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen... View all property information
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$250
Per Night
1 / 20
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3 Bedrooms, 1 Bathroom, Sleeps 7
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Amenities & Details
  • Refrigerator
  • Hot Tub
  • Stove
  • Fireplace
  • Garage
  • Washer
  • Parking
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming 3BR 1BA cape cod is 1 1/2 miles from City Dock and USNA. Enjoy the large back yard with two-level patio, hot tub and fire pit. Master bedroom has king bed. Second bedroom has a queen sized bed. Air mattress available in office for third bedroom. Additional queen air mattress available... View all property information
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From
$169
Per Night
1 / 4
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3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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Amenities & Details
  • Dryer
  • DVD Player
  • Dishwasher
  • Washer
  • VCR
  • Ceiling Fans
  • Refrigerator
  • Microwave
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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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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From
$300
Per Night
1 / 9
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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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From
$500
Per Night
1 / 11
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1 Bedroom, 2 Bathrooms, Sleeps 4
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This is the newly renovated 3-story open plan live-work unit that is connected to the main house that is similarly titled as the main house (1) and the studio apartment (2) - not included with this listing. Striking and dramatic 1500 - 1600 sf contemporary, open plan loft style renovation with a... View all property information
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From
$1,500
Per Night
1 / 15
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4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Stove
  • Dishwasher
  • Microwave
  • Refrigerator
  • Garage
  • Patio
  • Dryer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation and building addition with exposed structure and mechanical systems that serves as the architect - owner's live-work getaway. The main house has a 4 stop elevator, 2 car garage, master bdrm and bath suite, 3 additional... View all property information
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From
$400
Per Night
1 / 7
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Microwave
  • DVD Player
  • Stereo System
  • Grill
  • Dishwasher
  • Fireplace
  • Patio
  • Dryer
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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From
$700
Per Night
1 / 6
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5 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • DVD Player
  • Microwave
  • Patio
  • Fireplace
  • Refrigerator
  • Washer
  • Grill
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Our home is brand new & only one block from the Naval Academy Stadium on Gibson Rd (you can see the stadium from M. bedroom balcony). With, 4 bedrooms upstairs & 1 bedroom down, all the bedrooms have their own full bath. There is also a family room on the second floor with a mini bar, sink & pull... View all property information
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From
$695
Per Night
1 / 25
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5 Bedrooms, 3 Bathrooms, Sleeps 21
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Amenities & Details
  • Hot Tub
  • DVD Player
  • Washer
  • Canoe
  • Microwave
  • Refrigerator
  • Dishwasher
  • Patio
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 2014) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden... View all property information
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From
$250
Per Night
1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Washer
  • DVD Player
  • Grill
  • Microwave
  • Stove
  • Dryer
  • Garage
  • Refrigerator
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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From
$850
Per Night
1 / 24
4 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Hot Tub
  • Stove
  • Patio
  • Fireplace
  • Refrigerator
  • Dishwasher
  • Grill
  • Microwave
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. This incredible home has 100’ of floor-to-ceiling windows nestled in the tree canopy for expansive views of Weems Creek. Decks span the entire house 65' above the water. There are 4 full baths and 4 bedrooms... View all property information
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From
$400
Per Night
1 / 13
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Deck
  • VCR
  • Grill
  • Dryer
  • Washer
  • Patio
  • Dishwasher
  • Refrigerator
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. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac neighborhoods and features spacious parking in driveway for four cars. The Kimber Ridge Home is... View all property information
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Suitability

  • Wheelchair access (5)
  • Elder access (5)
  • Suitable for children (11)
  • Pet friendly (7)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (15)
  • Internet (15)
  • Other outdoor space (15)
  • Washer/Dryer (14)
  • Grill (13)
  • View all amenities