Homes with Pools

Maryland Vacation Rentals with Pools

Make your Maryland Eastern Shore vacation one to remember and book one of our rental homes with a private pool! There is nothing like having your own refreshing private pool to cool off after a fun day on the water fishing, crabbing, or just sightseeing. Perfect for larger groups, many of these vacation rental homes come complete with lounging and patio furniture as well as grilling tools for the perfect backyard hangout!

Our swimming pools are open from May 15-October 15. Some homes do offer pool heat at an additional charge; please inquire for more details. Also, note that the early and late parts of the season may affect water temperatures, however, pools are open to maintain the ambiance of the property.

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)

$540.00

Swan's Rest
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Swans Rest
  • Pets Allowed
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Starting at (USD)

$590.00

Thistle Dew
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Thistle Dew
  • Pets Allowed
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Starting at (USD)

$1,045.00

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

$880.00

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

$800.00

Tricefields
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Tricefields
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Starting at (USD)

$500.00

Tuckaway Cove
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Tuckaway Cove
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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)

$1,084.00

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