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Chesapeake Mansion-heated pool 30acre waterfront
Dive Into Luxury at a Premier Waterfront Estate
Reserve this StayResidence in Sherwood, MD
/Chesapeake Mansion-heated pool 30acre waterfront
Chesapeake Mansion-heated pool 30acre waterfront
8 Bedrooms
11 Bathrooms
5.0 (33 Reviews)
Discover the pinnacle of luxury and serenity at the Chesapeake Mansion, a stunning 12,000 square-foot estate nestled on 30 acres of private land in Sherwood, Maryland. This premier destination is situated just outside the charming town of St. Michaels and is the perfect setting for an unforgettable vacation. Voted the #1 mansion rental in Maryland by Trips to Discover, and recognized by Conde Nast Traveler as the coolest Airbnb in the state, this property combines vast open spaces with exclusive, high-end amenities. The mansion’s design is a beautiful blend of sophistication and comfort, ensuring that every guest experiences the highest standard of living.
Boasting eight spacious bedrooms, 11 luxurious beds, and 11 modern baths, the Chesapeake Mansion comfortably accommodates up to 12 guests. Whether you’re hosting a family reunion, a corporate retreat, or simply seeking a getaway with loved ones, every detail is designed with your comfort in mind. The expansive living areas are adorned with tasteful furnishings, offering plenty of room to relax or entertain. The fully equipped kitchen is perfect for preparing gourmet meals, while the bar area and game room offer endless entertainment for all ages.
Step outside to find a heated, saltwater pool with ample seating, a fire pit for cozy evenings, and a 160-foot private pier extending into the sparkling waters. The estate’s vast grounds provide plenty of space for outdoor activities, including a large playground for children, a garage bay for sports, and recreational equipment. The nearby St. Michaels offers a quaint, picturesque escape, but it’s the tranquility and beauty of the estate that will leave a lasting impression.
From the moment you arrive, the Chesapeake Mansion delivers an experience unlike any other. Whether you’re lounging by the pool, enjoying a family barbecue, or simply taking in the breathtaking water views, this estate invites you to slow down, relax, and create lasting memories in one of Maryland’s most luxurious settings.
Discover the pinnacle of luxury and serenity at the Chesapeake Mansion, a stunning 12,000 square-foot estate nestled on 30 acres of private land in Sherwood, Maryland. This premier destination is situated just outside the charming town of St. Michaels and is the perfect setting for an unforgettable vacation. Voted the #1 mansion rental in Maryland by Trips to Discover, and recognized by Conde Nast Traveler as the coolest Airbnb in the state, this property combines vast open spaces with exclusive, high-end amenities. The mansion’s design is a beautiful blend of sophistication and comfort, ensuring that every guest experiences the highest standard of living.
Boasting eight spacious bedrooms, 11 luxurious beds, and 11 modern baths, the Chesapeake Mansion comfortably accommodates up to 12 guests. Whether you’re hosting a family reunion, a corporate retreat, or simply seeking a getaway with loved ones, every detail is designed with your comfort in mind. The expansive living areas are adorned with tasteful furnishings, offering plenty of room to relax or entertain. The fully equipped kitchen is perfect for preparing gourmet meals, while the bar area and game room offer endless entertainment for all ages.
Step outside to find a heated, saltwater pool with ample seating, a fire pit for cozy evenings, and a 160-foot private pier extending into the sparkling waters. The estate’s vast grounds provide plenty of space for outdoor activities, including a large playground for children, a garage bay for sports, and recreational equipment. The nearby St. Michaels offers a quaint, picturesque escape, but it’s the tranquility and beauty of the estate that will leave a lasting impression.
What we love about this stay
Bring your own groceries and a good cook — the kitchen here is genuinely impressive, and the best meals you'll have on the Eastern Shore will be the ones you make yourself, eaten outside near the water. Walk the pier at golden hour; the light on the Chesapeake around 7 p.m. in summer is extraordinary, and you'll want a drink in hand for it. Skip St. Michaels on your first day — settle into the 30 acres, let the kids find the playground, claim your pool chair. The fire pit after dark is where the real conversations happen. For sleeping, grab one of the water-facing rooms early; waking up to that view before anyone else is stirring is the quietest luxury this place offers.
Explore the residence
11 Bathrooms
Member rates save up to 15% on every room
Free cancellation on most room types
Member rates save up to 15% on every room
Free cancellation on most room types
Browse the latest offers from Chesapeake Mansion-heated pool 30acre waterfront
Where you'll be staying
Sherwood, MD, US
Hear it from other travelers
Guest
MAR 2026
Absolutely amazing house! Loved all the space, the quality linens in the bedrooms, the light-filled rooms. Loved the ping pong table, workout room, and billiard room. Perfect for a relaxing mom’ getaway weekend.
Guest
MAR 2026
Amazing location, right on the water. Beautiful property that wowed our entire family, young and old. Our kids loved the toys and games in the game room and the fantastic playground. Older family members appreciated the tranquility and the incredible sunset views of the bay. Lots and lots of room for everyone in our party. Overall an amazing experience!
Guest
MAR 2026
Such a fun place for a retreat!
Guest
MAR 2026
What a beautiful location! The house was immaculate and the grounds well maintained. We enjoyed the space for our group and would love to come back again. Thank you Marissa for being so friendly and informative during our stay!
Guest
MAR 2026
Beautiful property and amazing host, point blank. It doesn’t get better than this listing. Our whole family had a peaceful vacation reset that we were looking for from our busy day to day. We honestly enjoyed the home so much that we barely had to leave it. We went out to eat for a couple meals but for the most part enjoyed the grill and cooking family meals. We did s’mores on most nights outside at the fire pit, spent our evenings watching the sunset on the pier and fishing (and occasional sunrises,) there are no limitations for this home.
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