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64 Houses

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Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,119

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$861

Waterview Cottage In St. Michaels!

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$382

Tranquil Easton Waterfront Property

Easton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$6,884

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

$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

$2,295

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

$1,893

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

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

$477

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

$1,951

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

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

$803

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,148

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$401

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$402

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$442

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$343

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$573

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$683

“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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Price per night from

$454

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$442

Cozy Downtown Annapolis Apartment

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$248

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$190

Annapolis Woodland Retreat

Cape Saint Claire house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$345

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$345

Breathtaking Waterfront Cambridge Getaway

Cambridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$683

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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Price per night from

$459

Serene Waterfront Apartment on Kent Island

Stevensville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$230

Fox Hollow House

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$459

2 parking spots and Walkable to Main Street at Seashell in the City

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$466

Historic Carriage House in the Heart of Downtown Annapolis

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$730

Duke's Den Downtown home with 2 PARKING spots!

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$641

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

$417

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

$909

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$408

Walk to waterfront & USNA with Parking at Historic Wisteria

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$466

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