Guest
MAR 2026
We celebrated a 50th birthday here. Made great meals at the house and drinks at the bar. Rooms were well appointed and the setting is quiet and private.
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
Where you'll be staying
Sherwood, MD, US
Hear it from other travelers
Guest
MAR 2026
The house exceeded our expectations for my birthday weekend. It had a lot of areas to congregate as well as spread out. The view of the Chesapeake Bay from the house was majestic. Big thank you to the host Marissa for making our stay perfect in ever way.
Guest
MAR 2026
This was a perfect house for our group of 9. Beautiful property, big nice house, close to Tilghman and St Michaels. Marissa was very responsive and helpful to all questions, and check in and out was a breeze. Would definitely stay again!
Guest
MAR 2026
Marissa made the entire process very smooth with her quick and positive responses. The interaction was great.
Guest
MAR 2026
Great stay at Chesapeake Mansion! <br/>We grilled(some amazing meat and fish from Chesapeake Seafood & Prime Meats in St. Michaels) and fished/crabbed on the wonderful pier. Cooked s'mores on the outdoor fire pit. One year old granddaughter loved the outdoor playground as well as the playroom inside!<br/>Terrific kitchen with great appliances. There's also pool, ping pong and a foosball table.<br/>Sitting outside in the Adirondack chairs was so peaceful. You can't beat the views of the bay and loved watching the pair of bald eagles that nest nearby. <br/>It's a very quick trip to St. Michaels and even closer to Tilghman Island.<br/>Hated to leave!
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