UNIQUELY DESIGNED FOR WHAT MATTERS TO YOU.

OUR HOMES ARE PERSONALLY OWNED, MANAGED, AND HOSTED BY US.

THIS SOLIDIFIES AN UNMATCHED EXPERIENCE AND ALLOWS US TO DELIVER THE DIRECT ATTENTIVENESS YOU DESERVE. EACH OF OUR PROPERTIES HAS BEEN HANDPICKED AND EXTENSIVELY OUTFITTED WITH YOUR COMFORT IN MIND AND DESIGNED FOR ENTERTAINING MULTIPLE GENERATIONS OF GUESTS. EMBRACE THE LUXURY AFFORDED BY CHESAPEAKE MANSION, THE EXCLUSIVITY FOUND AT THE RANCH AT ROYAL OAK, OR THE SPECTACULAR LOCATION AND WHIMSY OF SPENCER CREEK CABIN - WE HAVE A PROPERTY THAT WILL FEEL LIKE HOME FOR YOU AND THOSE YOU LOVE. WE LOOK FORWARD TO HOSTING YOU!

Chesapeake Mansion

Why We Love It

CHESAPEAKE MANSION IS THE PREMIER EASTERN SHORE DESTINATION. THIS ENORMOUS 12,000 SQ. FT. MANSION SITS ON A PRIVATE 30 ACRES JUST OUTSIDE OF ST. MICHAELS. THE ENTIRE HOME WAS RENOVATED FROM TOP TO BOTTOM

WITH YOUR VACATION IN MIND! WHETHER YOU SEEK TO SPEND YOUR DAYS MAKING MEMORIES INDOORS, SPLASHING IN THE POOL, OR SIMPLY TAKING IN THE BREATHTAKING WATER VIEWS...THIS 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

License #: ST-214-LYT
- Atlantic Broadband high speed internet service with mesh wi-fi
- Gated private gunite heated pool (up to 8 feet deep) with 4 chaise lounges & 8 adirondack chairs
- Fully equipped kitchen, complete with state-of-the-art appliances & high-end kitchen accessories
- Mansion Bar with billiard area and foosball table
- Full bar - 16 feet, full refrigerator, dishwasher, & sink
- 5 TVs
- Fitness room with elliptical, recumbent bike, yoga mats, & dumbbells (5lb & 10lb)
- 8 burner grill outside with picnic seating & umbrellas
- Garage bay with outdoor activities to play softball, soccer, football, cornhole, & Kan Jam
- Large playroom for the kids, stocked with toys
- New poly-wood waterfront playground
- 160' pier and 5' MLW
- 12,000 square feet with ample space for 12 guests (county maximum)
- Elevator (available upon request)
- 1000'+ private rip-rapped/bulkhead shoreline

EXPLORE PROPERTY

Ranch At Royal Oak

Why We Love It

Serenity and surreal views await you at your exclusive waterfront pool pier across 10 gorgeous acres. This majestic peninsula is private, yet within close proximity to St. Michaels and Easton for cafes, shopping, or an evening meal adventure. We guarantee you’ll fall in love with Royal Oak…and maybe asleep in one of our lovely adirondack chairs overlooking picturesque Chesapeake Bay.

License #: ST-251-LYT
- Satellite internet with mesh wifi
- Outdoor shed includes 2 kayaks, life jackets, and cornhole
- Brand new poly-wood waterfront playground
- Crab pots
- Fully equipped kitchen, complete with state-of-the-art appliances & high-end kitchen accessories
- Extra large dining room table for 12
- Bikes
- Multiple Smart Tv’s
- 12’ Shuffleboard table
- 8-burner grill outside with picnic seating & umbrellas
- Screened in porch with abundant seating
- 4500 sq.ft. with ample space for 12 guests
- Private pier

EXPLORE PROPERTY

Spencer Creek Cabin

Why We Love It

THIS IS THE HOUSE THAT STARTED OUR LOVE AFFAIR WITH ST. MICHAELS. SPENCER CREEK CABIN IS SO SPECIAL IN ALL OF THE MOST MEANINGFUL WAYS. THIS SPACIOUS 6 ACRE PROPERTY PLACES YOU IN THE PERFECT LOCATION FOR A CLASSIC ST. MICHAELS GETAWAY. HERE YOU WILL ENJOY ALL THE TOWN HAS TO OFFER, ANCHORED IN A PRIVATE SETTING WHERE YOU CAN FOCUS ON THOSE YOU'RE WITH. RISE UP COFFEE, GRAUL'S MARKET, AND CHESAPEAKE SEAFOOD ARE

JUST ACROSS THE STREET AND HISTORIC DOWNTOWN ST. MICHAELS IS BARELY A MILE AWAY. STAY HERE AND YOU'LL BE BACK!

License #: ST-214-LYT
- Satellite internet with mesh network
- Poolside deck with bar-top and 4 bar-height adirondack loungers
- Private heated pool
- 2 kayaks and life jackets
- Brand new poly-wood waterfront playground
- Fully equipped kitchen, complete with state-of-the-art appliances & high-end kitchen accessories
- 6 bikes
- Outdoor shed includes additional outdoor supplies
- Big screen TV (DirecTV & DVD)
- Rec Room: pullout sofa, air hockey/pool table, board games, puzzles, & teepee
- Grill & picnic seating with umbrella
- Sun Room with dining & bar seating
- Side deck with 4 adirondack chairs
- 3500 square feet with ample space for 8 guests
- Coffee Shop, Local Supermarket, Seafood Market across the street
- Within bike-riding distance to St. Michael’s

EXPLORE PROPERTY

PUNCH POINT

Why We Love It

Welcome to Punch Point! The years of design work for our guests have culminated with this new listing. The rehab mission being; provide our guests with more. it is a fresh, fun, and vibrant space that encourages community. There is an abundance of comfortable areas to lounge, both indoors and out. Enjoy the heated pool. Launch the kayaks from our eastern shore-style sandy beach. Smile at your loved ones by the firepit. Take it all in and share the love we have for St. Michaels.

License #: STN-23-46
- Fully equipped kitchen, complete with state-of-the-art appliances & high end kitchen accessories. 36” refrigerator and 36” freezer
- Additional refrigerator in upstairs lounge
- Gas stove
- Double islands
- Pool table
- Ping pong table
- Foosball
- Shuffleboard
- Putting green
- Kids playroom with toys
- Mario Bros. Themed garage play area
- 4 big screen TVs
- Massive all-season room (temp- controlled)
  Heated pool
- Sandy beach (a rarity on the eastern shore)
- Brand new playground
- Bikes
- Kayaks
- 6000 sq ft, 10 max guest

EXPLORE PROPERTY

An Opportunity of a Lifetime - The Links at Perry Cabin

Booking a stay with Tremezzo grants you the opportunity for sponsored play at this iconic and exclusive luxury club.

Links at Perry Cabin is designed by the legendary Pete Dye and plays through stunning topography and vistas of Maryland’s iconic Eastern shore—including majestic trees, bunkers, and distinctive water features—and ends with an unforgettable finishing stretch in view of the glorious Chesapeake Bay.

Reach out to us if you desire a tee time!

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