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CHESAPEAKE MANSION

The epitome of luxury

Font view of Chesapeake Mansion

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. 

Interior staircase of Chesapeake Mansion

YOUR GRAND ENTRANCE AWAITS

Walk through the front double doors and into a life of luxury, tranquility, and bespoke design. 

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 

BOOK YOUR STAY
BOOK YOUR STAY
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“We had a truly wonderful and exceptional experience! The mansion is absolutely stunning and was everything we were looking for and more. I will indubitably remember this experience for the rest of my life. An absolutely top-notch weekend. This stay was also unlike any other Airbnb experience I've had previously; there was nothing more that we could have asked for. Marissa was also super accommodating and hyper-responsive with any requests or questions we had prior to our arrival and during our stay.

If it were an option to leave more than 5 stars, I would. It was that incredible.”

JOHN

PROPERTY DETAILS

    • 12,000 square feet

    • 30 acres

    • Maximum occupancy 12

    • Elevator (available upon request)

    • Fully equipped kitchen, complete with state-of-the-art appliances & high end kitchen accessories

    • gas stove

    • Full bar - 16 feet, full refrigerator, dishwasher, & sink

    • 5 TVs

    • Atlantic Broadband high speed internet service with mesh wi-fi

    • Mansion Bar with billiard area and foosball table

    • Fitness room with elliptical, recumbent bike, yoga mats, & dumbbells (5lb & 10lb)

    • Large playroom for the kiddies, stocked with toyS and ping pong table

    • heated pool - gunite and gated

    • 4 chaise lounges & 8 adirondack chairs

    • 160' pier and 5' MLW

    • 1000'+ private rip-rapped/bulkhead shoreline

    • fire pit

    • grill outside with picnic seating & umbrellas

    • Garage bay with outdoor activities to play softball, soccer, football, cornhole, & Kan Jam

    • brand New supersized poly-wood waterfront playground

FLOOR PLANS

  • A cozy bedroom with a wooden four-poster bed dressed in blue and orange-patterned pillows and a red quilt. A teal nightstand with a lamp is on the left. There is a vintage dresser with a framed mural that says 'Bon Voyage,' and a mirror in the adjacent room. The floor is wooden, with a colorful patterned rug near the foot of the bed.

    BEDROOM 1

    1 KING BED | EN SUITE BATHROOM | SHOWER

  • A bedroom with yellow walls, a large bed with yellow and cream pillows, a blue throw blanket, a wooden dresser with a lamp, a decorative mirror, a patterned rug, and a chandelier.

    BEDROOM 2

    1 KING BED | EN SUITE BATHROOM | SHOWER

  • A cozy attic bedroom with two twin beds with blue bedding, floral headboards, striped pillows, and a colorful rug on a wooden floor. The walls and ceiling are painted light green with geometric accents, and there's a closed white door in the center.

    BEDROOM 3

    3 Full beds

  • A bedroom with a wooden four-poster bed, blue and white bedding, and framed artwork above the headboard. The room has blue ceiling, white walls, hardwood floors, and a window with blue curtains. There are two lamps with white shades on nightstands on either side of the bed.

    BEDROOM 4

    1 KING BED | EN SUITE BATHROOM | SHOWER

  • A bedroom with teal walls, a metal bed frame, white bedding with black floral pattern, three purple pillows, wooden nightstand with a lamp, decorative mirrors on the wall, a window with sheer curtains and a view of the ocean, a patterned rug, and a ceiling chandelier.

    BEDROOM 5

    1 KING BED | EN SUITE BATHROOM | TUB

  • A bedroom with a wooden four-poster bed, green walls, colorful pillows, and wall art of a woman sitting, with curtains and a window in the background.

    BEDROOM 6

    1 KING BED | EN SUITE BATHROOM | TUB | DUAL VANITY

  • A cozy bedroom with a yellow bedspread, white pillows, and a green blanket. The room has a sloped ceiling with yellow-patterned wallpaper and a framed cat artwork on the wall. There are two bedside lamps and a window with a blue and white patterned shade, revealing a bright outdoor scene.

    BEDROOM 7

    2 Queen beds | Crib | Shared bathroom with Room 8

  • A bedroom with a sloped white ceiling, beige walls, and a hardwood floor. There is a bed with an orange upholstered headboard, white quilted bedspread, and plaid pillows. Two wooden nightstands with lamps flank the bed. A wooden dresser with three drawers and decorative items is on the left, and a rug with stripes covers part of the floor. Gold-colored wall art and mirrors are above the dresser.

    BEDROOM 8

    1 KING BED | EN SUITE BATHROOM | TUB

Chesapeake Mansion st. michaels maryland
Pool Table at the Chesapeake Mansion
east coast vacation for family Chesapeake Mansion
maryland house rental
ECLECTIC STYLE TRENDY VACATION
FAMILY RETREAT ST. MICHAELS
EASTERN SHORE LUXURY CHAISE LOUNGE
CHESAPEAKE LIVING AND DESIGN
PRIVATE LUXURY BAR WATERFRONT
PING PONG KIDS ACTIVITIES FAMILY FUN
A grassy backyard with a swimming pool, surrounded by umbrellas and outdoor furniture. There is a play structure with a blue slide in the foreground, and the ocean can be seen in the background under a partly cloudy sky.
COFFEE BAR AT THE MANSION FAMILY GATHERING AND RELAXATION
ORIGINAL ARTWORK BEST RENTALS
FAMILY TIME MEMORIES
CHESAPEAKE MANSION REAL HOUSEWIVES ENTRANCE
LARGE OPEN WATERFONT KITCHEN EASTERN SHORE VACATION RENTALS

What people are saying

  • “It was so impressive how every detail was considered, from the decor to the comfort of the pillows to the sharpness of the knives. Every inch of the space was absolutely gorgeous, including the view!” - Megan | Chesapeake Mansion

    Megan | Chesapeake Mansion

  • “This home was beautiful. Marissa is an incredible host who was very responsive and accommodating. The house was gorgeous. We have rented many houses (from the Hamptons to the Jersey beaches to the Poconos) and this has by far been our favorite. The decor was incredible and the rooms were beautiful. Morning coffee with that view is the best and the BREATHTAKING sunsets every night were even better! We had three generations there and everyone had a wonderful time.”

    Jillian | Chesapeake Mansion

  • “Easily the best AirBnB we have ever stayed at. It has every single item you could need, immaculate interior design, extremely comfortable accommodations. We told everyone around the local town about this property. We’d recommend it to anyone and would definitely stay again. The host was kind, responsive, and prepared which is always a huge bonus.”

    Emily | Chesapeake Mansion

  • “Thank you for a WONDERFUL stay! We had three toddlers with us, I hope this is their first memory :)”

    Kareem | Chesapeake Mansion

  • “I have stayed in Airbnb’s and hotels all over the world. The stay at the mansion was up to the level and beyond of anywhere I have stayed before. The host did a great job communicating and there is nothing about this I would change.”

    Gordan | Chesapeake Mansion

  • “My executive team and managers enjoyed using the house for our meeting. The large sitting area with lots of windows looking over the bay was the perfect setting to let them relax and share their ideas. Plus there are wonderful restaurants nearby in St Michael’s. We typically move our annual meeting to different places but they asked to come back here again next year. If you are planning a family vacation, they keep the house well stocked with both kitchen supplies and various games for both outside and inside. It is also great watching the bald eagles that nest nearby.”

    James | Chesapeake Mansion

  • “Marissa is so attentive to detail and super responsive. The home was stunning and perfect for our large multi-generational crew. There was something for everyone. The views of the bay are unmatched. Thanks for sharing your home.”

    Tricia | Chesapeake Mansion

  • “Everything about the Chesapeake Mansion was absolutely perfect! The house is a dream - immaculate, beautifully decorated, spacious and well stocked with everything you could need. It was the perfect set up for our group of young families and had everything needed for traveling with little ones and keeping them entertained. The kids loved the playground and well stocked playroom. The adults loved the pool table and bar set up. The sunset views were absolutely breathtaking. The new dock was an added plus. The location was amazing - we enjoyed spending the day in St Michaels and biking to Tilghman island. Chesapeake Landing was highly recommended for seafood takeout and did not disappoint - we were thrilled that the house even had crab crackers/mallets for eating crab. Marissa was a wonderful host and was very quick to respond and address any questions. We hope to be back again soon!!”

    Colleen | Chesapeake Mansion

  • “One of the best Airbnb experiences I've ever had. Marissa is super responsive, thorough in the information she shares to make the most of your stay, and helpful during your stay. The setting is gorgeous, and the home is well stocked with any essentials you may need. St Michael's has a cute downtown with awesome cafes and restaurants that's only 15 minutes away. Anyone considering this home for a group reunion or family vacation should look no further. The host and home are both highly recommended. You will not be disappointed.”

    Giri | Chesapeake Mansion

  • “The house and grounds at ChesMansion are truly one of a kind. It is an extravagant home in a special location with a very responsive host. It has plenty of space to spread out and have some privacy even with a large group. It had all the amenities you’d expect and more. The pool was lovely, and sitting on the lawn watching the sunset was just gorgeous. We also discovered the fishing right at the shore was great, especially right at dusk. And St. Michaels was super close so we could enjoy a dinner out or some shopping. Our group enjoyed every minute we could muster at Ches Mansion, and I look forward to returning sometime soon.”

    Mike | Chesapeake Mansion

Stay with Tremezzo Stay and Play the Links at Perry Cabin. This is a cherished Pete Dye course design. Best golf in Maryland.

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. 

A scenic golf course with green fairways. Stay with Tremezzo Stay and Play the Links at Perry Cabin. This is a cherished Pete Dye course design. Best golf in Maryland.

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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YOUR VACATION AWAITS

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