View All Properties

Feel free to browse our great selection of cottages, waterfront homes and estates. We would be happy to help you find just the right spot for your vacation! 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)

$950.00

The Dinghy
Bozman-Neavitt
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: The Dinghy
  • Pets Allowed
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Chestertown
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: The Tree House
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Starting at (USD)

$635.00

Thistle Dew
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Thistle Dew
  • Pets Allowed
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Starting at (USD)

$1,194.00

Thornton Farm - Grace and Elegance
Chestertown
  • 11 Guests
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Code: Thornton
  • Pets Allowed
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Starting at (USD)

$885.00

Tides Out
St. Michaels
  • 12 Guests
  • 6 Bedrooms
  • 3 Bathrooms
  • Code: Tides Out
  • Pets Allowed
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Starting at (USD)

$870.00

Town & Country
St. Michaels
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Town & Country
  • Pets Allowed
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Starting at (USD)

$465.00

Town Creek Haven
Oxford
  • 8 Guests
  • 3 Bedrooms
  • 3.5 Bathrooms
  • Code: Town Creek Haven
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