Houses St. Michaels

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Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$859

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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Price per night from

$716

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,290

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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Price per night from

$2,290

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

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,890

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Waterview Cottage In St. Michaels!

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$382

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$352

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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Price per night from

$487

“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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$453

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

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$476

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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$458

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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Price per night from

$1,947

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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Price per night from

$1,947

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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Price per night from

$802

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,145

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$400

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$401

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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Price per night from

$796

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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Price per night from

$2,863

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$630

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$572

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$682

Breathtaking Waterfront Cambridge Getaway

Cambridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$682

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

$401

Waterfront home with private pier is A Shore Thing

Chester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

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Price per night from

$429

Stay at Lux Red Door Gem with 3 Parking Spots

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$382

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Price per night from

$637

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$729

Cottage by the Bay on one level in family-friendly community

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$367

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

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$416

Historic Carriage House in the Heart of Downtown Annapolis

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$343

Stay just steps from the Waterfront in the modern Historic Fleet's Inn

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$405

"Around the corner" from everything, private backyard and parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$384

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Price per night from

$355

Private Waterview Estate with 4 bedroom Suites & Hot Tub

Shady Side house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$429

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$727

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$465

180-degree water views at unique round house

Shady Side house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$367

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rentals in St. Michaels

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