Personally Hosted Luxury Rental Experiences
Personally Owned, Managed, and Hosted By Us
We named our luxury rental company Tremezzo Stay after our favorite trip ever: our honeymoon in Lake Como, italy. Because that’s the kind of lightning-in-a-bottle feeling you get when you stay with us - we bring you memories that will last a lifetime.
BRINGING YOU THE MID-ATLANTIC’S PREMIER VACATION PORTFOLIO
Chesapeake Mansion
Chesapeake Mansion
Chesapeake Mansion
Chesapeake Mansion is the premier Eastern Shore destination. This enormous 12,000 sq. ft. mansion sits right on the edge of the Chesapeake Bay on a private 30 acres just outside of St. Michaels. The entire home was renovated from top to bottom with your vacation in mind! From splashing in the pool, stepping out on the 160-ft pier for breathtaking bay views, or challenging your party to a game of foosball or billiards should a few clouds come your way, this stunning vacation home has something for everyone to enjoy.
Voted Coolest Airbnb in the State of Maryland by Conde Nast Traveler
Voted #1 Mansion Rental in the State of Maryland by TripsToDiscover.com
Host to the Bravo TV Network’s The Real Housewives of Potomac
Accolades & Honors
ranch at royal oak
ranch at royal oak
ranch at royal oak
Serenity and surreal views await you at Ranch at Royal Oak. Your exclusive waterfront pool and pier across 10 gorgeous acres has it all. With 6 bedrooms, sweeping majestic views, playground, boat slip, firepit and more, all while being in close proximity to both St Michaels and Easton, you’ll see why Royal Oak has been generating a lot of traveler buzz.
Whether your gaze lingers on the white picket fenced pastures while leaning back in a rocking chair on the front porch or you overlook the picturesque Chesapeake Bay cuddled up in an oversized adirondack chair – we guarantee you’ll find serenity at every corner of this former friesian horse farm.
Take Your Tremezzo Stay to the Next Level
Booking with Tremezzo Stay grants you the opportunity for sponsored play at the newest and most exclusive private club in the Mid-Atlantic, the world-renowned Links at Perry Cabin.
Spencer Creek Cabin
Spencer Creek Cabin
Spencer Creek Cabin
With 5 bedrooms on 6 exquisite waterfront acres, this location is perfect for any group looking for exclusive privacy while being close to it all. Just across the street, you’ll find a superb grocery store, gas station, Rise Up Coffee stand, and seafood market, while a 5-minute bike ride brings you right into Historic Downtown Saint Michaels. Enjoy our in-ground pool, playground, family-fun recreational room, sweeping water views, expansive landscapes, and the company you’re with!
What people are saying
Our Personalized Recommendations
Rich with eclectic small towns, pristine natural beauty, and unparalleled charm, the Eastern Shore of Maryland has so much to offer any vacationer looking for a memorable getaway. From the quaint historic harbors of St. Michaels to the private, picturesque views from your shorefront rental, we quickly realized it was impossible not to love this area.
And we want you to fall in love too! We’ve finely combed through Maryland’s Eastern Shore to bring you a little bit of everything - from the best restaurant recommendations to the most breathtaking bike rides - we offer thoughtful activity ideas for every age in your group. Explore our guides tailor-made for your perfect vacation!
The TREMEZZO STAY Treatment
For those who love a great before vs. after, we’re giving you a behind-the-scaffolding peak into the Tremezzo Stay property renovation process. We're always adding a bespoke feature or reconceptualizing a room in our properties - offering that extra touch of one-of-a-kind luxury for our guests is what brings us joy.
Keep in Touch with Tremezzo Stay
ASK US ANYTHING
ASK US ANYTHING
gET IN TOUCH
We’re here to help answer any questions you may have about our properties or the area before booking.