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Maryland Vacation Rentals: Cottages, Waterfront Houses, and Luxury Homes

Check out the category groups below to find your next Eastern Shore vacation rental in Maryland! Located in and around the St Michaels area, our vacation rentals offer great opportunities for exploring, adventure and relaxing. Enjoy breathtaking scenic views of the bay, hot tubs, fire pits, and beautifully cared for properties. We offer a complete selection of vacation rentals including Maryland waterfront rentals with breathtaking views, cozy cottages, and large family estate properties. Whether you are traveling as a couple, small family, or large group we have the perfect vacation rental for your Maryland getaway.

Guests often take advantage of nearby fishing and crabbing holes as well as the area beaches and attractions. Whether you are looking to get outdoors, see the nearby towns, or spend the days on the sand, our wide variety of vacation rentals offer great amenities and features youll enjoy during your trip.

Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

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Starting at (USD)

$665.00

Holland Point Preserve
Taylors Island, MD
  • 14 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: Holland Point Preserve
  • Pets Allowed
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Starting at (USD)

$1,300.00

Hudson Manor
Cambridge, MD
  • 22 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Hudson Manor
  • Pets Allowed
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Starting at (USD)

$630.00

Indian Fields
Cambridge, MD
  • 13 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Indian Fields
  • Pets Allowed
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Starting at (USD)

$600.00

Judith's Garden
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Judith`s Garden
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Starting at (USD)

$715.00

Loblolly Cove
Neavitt, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
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Starting at (USD)

$395.00

Mallard Point Cottage
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
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Starting at (USD)

$600.00

McKendree Street Mainland
Annapolis, MD
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: McKendree Street Mainland
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Starting at (USD)

$260.00

Memory Lane
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Memory Lane
  • Pets Allowed
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Starting at (USD)

$680.00

Mill Creek
Wye Mills, MD
  • 10 Guests
  • 5 Bedrooms
  • 3.5 Bathrooms
  • Code: Mill Creek
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Starting at (USD)

$750.00

Nantucket on the Chesapeake
Annapolis, MD
  • 10 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Nantucket on the Chesapeake
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Starting at (USD)

$975.00

Off the Grid
Oxford, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Off the Grid
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Starting at (USD)

$590.00

Osprey Point
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Osprey Point
  • Pets Allowed
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Starting at (USD)

$360.00

Oxford Beach Cottage
Oxford, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Oxford Beach Cottage
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Starting at (USD)

$735.00

Oxford Oasis
Oxford, MD
  • 12 Guests
  • 6 Bedrooms
  • 7 Bathrooms
  • Code: Oxford Oasis
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Starting at (USD)

$510.00

PennyWhistle
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
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Starting at (USD)

$680.00

Pines at Barrett Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • Pets Allowed
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Starting at (USD)

$495.00

Pines At Irish Creek
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Irish Creek
  • Pets Allowed
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Starting at (USD)

$295.00

Pride and Joy
Oxford, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pride and Joy Cottage
  • Pets Allowed
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Starting at (USD)

$350.00

Queen Anne
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Queen Anne
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Starting at (USD)

$300.00

Red Shake Cottage
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Red Shake Cottage
  • Pets Allowed
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Starting at (USD)

$1,237.00

Retreat on Grace Creek
Bozman, MD
  • 12 Guests
  • 6 Bedrooms
  • 8 Bathrooms
  • Code: Retreat on Grace Creek
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Starting at (USD)

$290.00

Simplicity Cottage
Tilghman Island, MD
  • 4 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Simplicity Cottage
  • Pets Allowed
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Starting at (USD)

$180.00

Sunflower Cottage
Oxford, MD
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Sunflower Cottage
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Starting at (USD)

$530.00

Sunrise Cove
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
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Starting at (USD)

$540.00

Swan's Rest
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Swans Rest
  • Pets Allowed
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