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100 houses

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$1,390

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$367

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$457

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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$573

Pet-friendly Edgewater cottage with hot tub near waterfront!

Edgewater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$240

Great rentals within 20 miles that match your search

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

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$489

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

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$454

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$477

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$805

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$52

Love Point Waterfront

Kent Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

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$460

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$1,954

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,954

One Beautiful home come relax

Cheltenham house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 6

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$202

JUTEWOOD LEVEL 2

Cheverly house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$138

Exquisite & Exclusive 3Bedroom 2Fullbath Upper Level Single Home

Riverdale Park house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

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$229

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$299

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,150

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

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$2,873

Creative 5 br/4.5 bth 4 Lvl House w/ Rooftop Garden Cafe

Greenbelt house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 5

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$977

Upscale 3 bedroom Townhouse

Odenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$230

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$401

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$443

Home Away From Home- 4 bedroom spacious home with great backyard space

Severna Park house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$288

The cozy enchanted escape

Glen Burnie house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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$460

Belle By the Bay

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$332

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$430

SeaGlass House by-the-Bay

Annapolis house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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$670

The Carrollton Cottage House

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$229

Family & Pet Friendly Home by Marinas & Recreation

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$401

West Annapolis Cottage

Annapolis house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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$916

Family Sized Contemporary in Spacious Neighborhood

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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$572

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$458

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$458

Nice ambient 5BDR with fast WiFi near Airport & Casino

Riviera Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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$572

Waterfront| 4BR| 1st Floor Master|Family Ready|Bwi

Glen Burnie house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$339

Annapolis Area Shagrila Resort

Davidsonville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$916

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,105

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