Houses St. Michaels

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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

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$860

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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$717

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

$2,293

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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$2,293

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

$1,892

Great rentals within 20 miles that match your search

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

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

“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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$476

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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$1,949

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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$1,949

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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$803

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,147

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$400

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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$2,866

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$458

Warwick River Retreat

East New Market house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

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$1,261

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

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$797

Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$631

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 18

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$860

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$572

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$682

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$430

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$442

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$402

SeaGlass House by-the-Bay

Annapolis house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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$671

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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$573

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

Tranquil Easton Waterfront Property

Easton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$6,877

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$1,106

Stunning, Newer Chesapeake Waterfront Estate, Pool - 7 Bedrms 5 Baths

Cambridge house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 18

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was clean and well furnished. The dining room table and table on the porch provided plenty of seating for meals. There was plenty of hot water for showers and clean-up after meals. The pool was clean and the river was awesome, with a gradual slope that was perfect for kids and adults. We used the crab traps provided and caught 2 dozen crabs that made a great contribution to dinner on Friday. Crabbing was best by the dock. We caught all but 3 crabs there, rather than out closer to the middle of the river. The AC on the ground floor stopped working on Tuesday, but one call to the owner and the repair team was on-site in less than 2 hours. The issue was resolved before noon on Wednesday. We have been renting vacation properties for years and issues crop up from time to time. We appreciated the quick response and resolution. The one recommendation we will make is to bring bug spray (mosquitos and horse flies). We anticipated it being right on the river, but if you haven't had that experience, you need to be prepared.

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Price per night from

$1,031

Breathtaking Waterfront Cambridge Getaway

Cambridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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$682

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$802

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$459

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$344

Luxury Waterfront home with private pier and guest house

Annapolis house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$907

Popular Historic Firehouse fully renovated with Parking and Pet Friendly

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$465

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