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Maryland Vacation Rentals: Cottages, Beach 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 ocean and bay, hot tubs, fire pits, and beautifully cared for properties. We offer a complete selection of vacation rentals including Maryland beach house 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)

$820.00

Tricefields - A Tidewater Colonial
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Tricefields
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Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: Waverly
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Starting at (USD)

$1,215.00

Willoughby
Cambridge, MD
  • 24 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Willoughby
  • Pets Allowed
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Starting at (USD)

$1,225.00

Woodwind
Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Woodwind
  • Pets Allowed
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