About Property

Discover the ultimate Eastern Shore getaway at the Chesapeake Mansion, a premier destination in Sherwood, Maryland. Voted the #1 mansion rental in the state by “Trips to Discover” and recognized by Conde Nast Traveler as the coolest Airbnb in the state, this extraordinary property has even played host to the Bravo TV Network’s Real Housewives. This enormous 12,000 sqft luxury home is designed for those seeking an expansive and prestigious retreat.

Designed to accommodate the county maximum, the estate features a grand layout with 8 bedrooms, 8 beds, and 11 bathrooms, comfortably hosting up to 12 guests. The home has undergone two years of thoughtful updates to ensure every rental need is met with sophistication. Guests have full access to the residence and the surrounding private 30-acre estate.

While structured amenities are limited, the property is renowned for its expansive outdoor features. Guests can enjoy the massive grounds, which include a new poly-wood mega playground with a pea-gravel surround and a 160’ pier. For those looking to relax, the pool is available from mid-April to mid-October. For an additional fee of $150 per day, the pool can be heated upon request, though heat maintenance cannot be guaranteed when outdoor temperatures drop below 60 degrees.

Perfectly positioned for exploration, the mansion is located just outside of St. Michaels. You are less than 15 minutes from the charm of downtown Saint Michaels and less than 5 minutes from Tilghman Island, offering the perfect balance of secluded luxury and local accessibility.

To ensure a seamless stay, the property offers keyless entry and an elevator available upon request. Please note the following house rules:

• Check-in: 4:00 PM
• Check-out: 10:00 AM
• Maximum occupancy of 12 guests at all times; no additional guests permitted
• No pets allowed
• No weddings or special events
• Proof of identification and a signed rental agreement are required within 48 hours of confirmation

Experience a personally hosted luxury rental where every detail is managed to provide an effortless and memorable stay at one of Maryland’s most celebrated estates.

This description is for informational purposes. Please verify all details, including amenities, policies, fees, and availability, on the booking platform before booking.