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“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

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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$459

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$459

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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$1,951

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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$804

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

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$429

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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$1,951

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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$321

Private pier at Waterfront Kent Island home with Hot Tub (Open!)

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$416

Great rentals within 20 miles that match your search

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$718

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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$488

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

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$477

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,148

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

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$2,296

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$401

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

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$276

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

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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$2,869

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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$2,296

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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$798

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$458

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$402

Belle By the Bay

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$368

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$632

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$573

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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$1,550

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$316

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$683

Neptunes by the Water

Cape Saint Claire house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$207

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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$1,894

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$431

Charming 3 bdrm cottage with lovely front porch

Rock Hall house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

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$229

Annapolis Woodland Retreat

Cape Saint Claire house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$345

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$442

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$861

Family Sized Contemporary in Spacious Neighborhood

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$630

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$353

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$803

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

Cape Saint Claire house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$402

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