Entire home in Sherwood, Maryland

12 guests
8 bedrooms
11 beds
11 baths

Hosted by TremezzoStay

Superhost
9 years hosting

Listing highlights

On the Chesapeake Bay near St. Michaels

On 30 private acres along the Chesapeake Bay, with St. Michaels about a 15-min drive away

A waterfront estate with a private pool

A 12,000 sq ft home with a heated pool, fire pit, ping pong and pool tables, and a playground

Marissa is a standout host

Guests highlight the bay views, comfortable beds, and Marissa's responsiveness throughout the stay

TREMEZZO STAY - Chesapeake Mansion
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rentals in St. Michaels, MD. We also own Tilghman Island Inn, a waterfront destination specializing in group retreats, weddings, and private events.

If you do not see availability for your dates please visit our additional exclusive listings!

Ranch at Royal Oak (sleeps 12)
Punch Point (sleeps 10)
Spencer Creek Cabin (sleeps 8)

The space
Chesapeake Mansion is the premier Eastern Shore destination. Voted #1 mansion rental in the state of Maryland by “Trips to Discover”! Also was host to the Bravo TV Network’s Real Housewives. The pool is open from mid-April to mid-October and to answer your question.. YES, it is heated :) This enormous 12,000 sqft. home sits on a private 30 acres just outside of St. Michaels. We spent 2 years updating this home with all of your rental needs in mind. This home sleeps the county maximum of 12 guests.
My husband and I have been hosts in the area for the last 5 years.

Please take a look at the virtual tour if you have a moment!

-March 2021- Atlantic Broadband has officially been added along with an EXTENSIVE MESH WiFi network!!!
-August 2021- New poly-wood mega playground installed
-October 2021- 160’ pier installed with 5’ MLW
-January 2022- Playground pea-gravel surround added

*#1 mansion rental in the state of Maryland by “Trips to Discover”
*Host to the Bravo TV Network’s Real Housewives
*Voted Coolest Airbnb in the state by Conde Nast Traveler

Talbot County Rental License: ST-214-LYT

Guest access
The entire home and 30 acres are available for your enjoyment.

Other things to note
**Pool Heater must be requested. There is a $150 per day fee for the pool to be heated. We cannot guarantee the pool will maintain heat when the outdoor temperature drops below 60 degrees.

It is completely very comfortable from June-September without any additional heat.

**There is an elevator available upon request