Chesapeake Estate

St. Michaels, Maryland
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  • Large waterfront residence situated on three acres overlooking the Miles River and Chesapeake Bay
  • Your own private pier, seasonally heated swimming pool, sprawling yard for lawn games, and fire pit
  • Expert concierge provided by Inspirato to make sure every detail of your stay is perfect
  • Read member reviews of our St. Michaels home here

ST-244-GII, 2019

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Features and Amenities

  • Stunning home on more than three acres of private property
  • Sweeping views of the confluence of the Miles River and Chesapeake Bay
  • 5-minute drive from charming downtown St. Michaels
  • Seasonally heated outdoor swimming pool
  • Private pier, for fishing and crabbing
  • Well-manicured backyard
  • Outdoor gas-fired fire table
  • Screened-in porch with fans
  • Vaulted ceilings
  • Two-car garage and uncovered outdoor parking for two additional cars
  • Air conditioning

Things to Know

  • This home is exclusively staffed, managed, and maintained by Inspirato.
  • This home's pool is heated seasonally and is open from Memorial Day through Labor Day.
  • Each of the four bedrooms features en suite bathrooms and there is an additional full bath and half-bath on the main level.
  • This home is located in a quiet residential neighborhood and no large gatherings are allowed.
  • While this home is on the water, we do not recommend swimming or enjoying water sports here due to the changing tides.
  • Internet connectivity in this home has been rated fast.

Additional Information:

  • The Standard Inspirato Cancellation Policy applies for this property. Please note the Peak Reservation policy applies for Christmas and New Year’s weeks and certain other travel dates.
  • Maximum occupancy: Stated occupancy cannot be exceeded.
  • Pet policy: No pets allowed.


The Bedding

  • Master Bedroom
  • Bedroom 2
  • Bedroom 3
  • Bedroom 4

Floor Plans

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