Chesapeake Estate

  • 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, 2018

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What’s included? More than you’d expect

This home is exclusively staffed, managed, and maintained by Inspirato. What does that mean? A lot. Here's what's included, all at no extra cost:

  • Personalized pre-trip itinerary planning
  • Pre-arrival grocery service so the kitchen is stocked when you get there
  • Expert on-site local staff
  • Daily housekeeping, including someone to do the dishes each day
  • Complimentary Wi-Fi to help you stay connected
  • Luxury furnishings, kitchen appliances, linens, and toiletries that meet our high brand standards
  • Professional home maintenance throughout your stay
  • Inspirato Care before, during, and after your trip (including emergency support)
  • No damage deposit or cleaning fee required

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's pool is heated seasonally and is open from Memorial Day through Labor Day.
  • Each of the four bedrooms feature 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.
  • Due to changing tides, please exercise caution when accessing the water.
  • The internet connectivity in this home has been rated fast.

Additional Information:

Members-only Benefit:

  • Enjoy 10% off your first boat rental and a complimentary wine and snack amenity with Boatsetter.

The Bedding

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

Floor Plans

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