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Vacation rentals and condos in Annapolis, MD

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All 18 Rentals in Annapolis
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$280
/ Night
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1 / 3
4 Bedrooms / 4 Bathrooms / Sleeps 8
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$169
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1 / 4
5 of 5 stars (2) Excellent
3 Bedrooms / 2 Bathrooms / Sleeps 4
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$400
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1 / 30
4.5 of 5 stars (2) Very good
4 Bedrooms / 3 Bathrooms / Sleeps 9
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$800
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1 / 31
5 of 5 stars (1) Excellent
3 Bedrooms / 2 Bathrooms / Sleeps 10
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Amenities & Details
  • DVD Player
  • Dishwasher
  • Safe
  • Microwave
  • Washer
  • Refrigerator
  • TV
  • Garage
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.... View all property information
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$750
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1 / 26
5 of 5 stars (2) Excellent
6 Bedrooms / 5 Bathrooms / Sleeps 13
travelers have booked this property
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Amenities & Details
  • Grill
  • Deck
  • Dishwasher
  • Parking
  • Stove
  • Refrigerator
  • TV
  • DVD Player
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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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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From
$400
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1 / 7
3 Bedrooms / 2 Bathrooms / Sleeps 8
travelers have booked this property
Overview Make Inquiry
Amenities & Details
  • TV
  • Refrigerator
  • Dryer
  • DVD Player
  • Fireplace
  • Grill
  • Washer
  • Stove
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
$150
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1 / 18
4 Bedrooms / 2 Bathrooms / Sleeps 8
travelers have booked this property
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Amenities & Details
  • Refrigerator
  • Parking
  • Ceiling Fans
  • Deck
  • Dryer
  • Stove
  • DVD Player
  • Washer
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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From
$700
/ Night
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1 / 6
5 Bedrooms / 6 Bathrooms / Sleeps 12
traveler have booked this property
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Amenities & Details
  • Parking
  • TV
  • Garage
  • Grill
  • Microwave
  • Dishwasher
  • DVD Player
  • Washer
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
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1 / 25
5 Bedrooms / 3 Bathrooms / Sleeps 20
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Amenities & Details
  • Dishwasher
  • Parking
  • Hot Tub
  • Patio
  • TV
  • Microwave
  • Fireplace
  • Washer
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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$250
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1 / 20
5 of 5 stars (1) Excellent
3 Bedrooms / 2 Bathrooms / Sleeps 6
traveler have booked this property
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Amenities & Details
  • Parking
  • DVD Player
  • Refrigerator
  • Microwave
  • Grill
  • TV
  • Washer
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 & 3 blocks from Spa Creek, is this charming, cozy, easy-living place to relax, entertain & enjoy nature. Plenty of free parking- two... View all property information
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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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From
$250
/ Night
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1 / 20
3 Bedrooms / 1 Bathroom / Sleeps 7
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Amenities & Details
  • Microwave
  • Dishwasher
  • Patio
  • Grill
  • Washer
  • Hot Tub
  • Refrigerator
  • Garage
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
$250
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1 / 23
3 Bedrooms / 2 Bathrooms / Sleeps 6
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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
/ Night
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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
/ Night
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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. 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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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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1 / 15
4 Bedrooms / 4 Bathrooms / Sleeps 10
travelers have booked this property
Overview Make Inquiry
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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1 / 11
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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1 / 6
4 Bedrooms / 3 Bathrooms / Sleeps 8
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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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