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Bay Estate | Luxe Waterfront Home w/ Private Pier, Main+Guest House, Bay Views

House in Dameron, MD

16 guests·7 bedrooms·5 bathrooms
4.7 · 7 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Private waterfront boardwalk and pier provide serene Chesapeake Bay evenings.

Entertainment & Amenities

Entertainment & Amenities

Chef-grade kitchen and abundant dining spaces inspire memorable group meals.

Group & Family Friendly

Group & Family Friendly

Ideal for large groups with private main and guest houses.

Property details

This is a buyout of two listings (Bay House and Bay Cottage) for a total of 7 bedrooms. Introducing Bay Estate, a pinnacle of luxury nestled in Dameron, Maryland, offering an exclusive waterfront experience on the shores of the Chesapeake Bay. This coveted retreat is a vision of grandeur, featuring a distinguished main home and a charming guest house. As you step onto the meticulously landscaped property, a private boardwalk and pier extend gracefully into the bay, inviting you to bask in the serenity of the waterfront location. You'll also be near a small pond where you can listen for wildlife. Expansive picture windows within the main house frame panoramic bay views, providing an uninterrupted connection to the natural beauty surrounding the home. Dual ovens and abundant counter space adorn the fully-equipped chef's kitchen, inviting culinary delights. You'll find two large dining tables on either side of the kitchen, giving your group plenty of space for meals or game nights with the water as your backdrop. You'll even find a unique conservatory room adorned with lush plants and striking rock features—an oasis for serene moments with a book or drink, and just one more way this retreat helps immerse you in nature. With seven bedrooms, including a sprawling primary suite with bay vistas and a luxurious ensuite featuring a circular shower and jacuzzi tub, Bay Estate epitomizes high-end living. Select bedrooms offer enchanting water views and private ensuites, ensuring every moment is one of indulgence. Step onto the stunning outdoor patio with an al fresco dining area and BBQ grill to savor the enchanting Chesapeake evenings. The guest house, a haven of privacy, expands the retreat, providing additional living space, two bedrooms, and a fully equipped kitchen. The combination of the main and guest houses makes this home ideal for large groups or multiple families. Amidst a large, private waterfront lot, Bay Estate captivates with an unparalleled sense of seclusion and exclusivity. Ideal for group travel, group retreats, or those seeking a Maryland waterfront escape, this residence promises an unforgettable rendezvous with luxury on the Chesapeake Bay. Dameron is nestled in the heart of Maryland and offers a serene escape from the hustle and bustle. Imagine a quaint town where history meets charm and nature invites you to unwind. With its historic architecture and tree-lined streets, Dameron exudes a timeless appeal. Explore local treasures like historical landmarks and cozy cafes. The community's warm embrace makes it an ideal retreat for group getaways. Start your morning with a scenic stroll through the historic district, where charming architecture tells tales of the past. Delve into the local culture by exploring museums that showcase Dameron's rich heritage. For nature enthusiasts, Dameron offers idyllic parks and trails, perfect for picnics or rejuvenating hikes. Make a splash in nearby waterways or simply unwind amidst the tranquil surroundings. Take advantage of the vibrant local markets, where you can savor delicious treats and shop for unique souvenirs. As the sun sets, gather with your group for a cozy dinner at one of the town's renowned eateries known for their bay-fresh seafood. Whether you seek history, nature, or culinary delights, Dameron invites you to create lasting memories. Local Attractions: Bittersweet Farms, Slack Wines at Woodland Estate & Inn, Cruisin Tikis Solomons Island, Historic St Mary’s City, Point Lookout State Park, SALT Waterfront Kitchen, Elms Beach Park Home Truths: - Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request. - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without approval there is a fine of $500 per pet. Parking Details: Bay House - There are 8 parking spaces available. Bay Cottage - There are 4 parking spaces available. --- The room configuration is as follows: Primary Bedroom: King bed w/ ensuite Bedroom 2: King bed w/ ensuite Bedroom 3: King bed Bedroom 4: 2x queen beds Bedroom 5 : King bed Bedroom 6 / 2x queen beds Bedroom 7 / Double bed + 2x tri-folds if requested --- This is a smoke-free property.. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 30 days require a security deposit. We report and prosecute all Credit Card Fraud. Pets - not allowed

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Queen Beds

Bedroom 4

1 Double Bed

Bedroom 5

1 King Bed

Bedroom 6

1 King Bed

Bedroom 7

2 Queen Beds

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Washer and dryer

    Washer and dryer

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Fireplace

    Fireplace

Guest reviews

Star icon 4.7 | 7 reviews
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M

Monica

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April 2026

The property itself is beautiful and the owner was kind, but unfortunately our overall experience was extremely disappointing due to the management through AvantStay. We had planned our wedding to take place outdoors at this private estate and communicated this nearly six months in advance. Despite this, our requests and concerns were either delayed or never properly addressed. For nearly $20K in total costs (including multiple unnecessary event fees), the experience did not meet expectations and was not worth the price. In the days leading up to the wedding, we encountered multiple serious issues that required us to spend almost two additional days resolving problems instead of focusing on our event. These included pests in the home, an exterminator spraying near my wedding dress, a door code that didn’t work upon arrival, and WiFi that was not functioning and required rerouting of the router. And so much more but I’m running out of “character availability”

J

Josh

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August 2025

Beautiful spot! Very private and quiet yet still relatively close enough for grocery shopping, dining (hush puppies at Salt are amazing), and checking out St. Mary’s City.

L

Lindsey

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June 2025

Quite and amazing views

R

Rushaad

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February 2025

The listing was great! Looks just like the photos and the host was VERY nice. Definitely would love to go back!

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 11:00am

No pets allowed

Min. age to rent: 25

No smoking

No parties

Have a question about this property?

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