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Chesapeake BayDameron, MD

Bay Estate

Bedrooms
7
Beds
9
Bathrooms
5
Guests
16
Sparkling Clean
Check our enhanced cleaning and sanitation protocols. Show details
Work-Friendly Space
Laptop friendly with high-speed WiFi.
Tech-Enabled Locks
Check yourself in with the keypad.
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:

The main house (Bay House) and guest house (Bay Cottage) are available to book individually.
Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.

Parking Details:
Bay House

There are 8 parking spaces available.
Bay Cottage

There are 4 parking spaces available.

Accidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 28 days or longer or reservations that require a security deposit.

All bookings over 28 days require a security deposit to be charged after booking.

Planning a Company Offsite or Social Event?

Get in touch with our Experience team.

What can I expect in the home?

  • Air Conditioning
  • BBQ
  • Private Parking
  • Heating
  • TV
  • Patio

Room details

Our home features 7 comfortable bedrooms for a perfect night's sleep.

Each room is outfitted with linens, towels, fluffy pillows and comforters. Linens are available for additional sleeping arrangements.

Sleeping arrangements

  • 4 xKing Bed
  • 4 xQueen Bed
  • Double Bed
Primary Bedroom (Bay House)
2 guests
King Bed, TV, Ensuite
Bedroom 2 (Bay House)
2 guests
King Bed, TV, Ensuite
Bedroom 3 (Bay House)
2 guests
King Bed, TV
Bedroom 4 (Bay House)
4 guests
2x Queen Bed, TV
Bedroom 5 (Bay House)
2 guests
King Bed, TV
Bedroom 6 (Bay Cottage)
4 guests
2x Queen Bed, TV
Bedroom 7 (Bay Cottage)
2 guests
Double Bed

House Rules

Club 21

You must be at least 21 years old to book this property.

Humans Only

Pets are not permitted at this property. Unauthorized pets may be subject to a fine.

Thank You For Not Smoking

This is a smoke-free home. Violation of the no-smoking policy will result in a $500 fee for additional cleaning and other related costs, in addition to the Guest being responsible for any damages attributable to smoking beyond said fee.

Respect Community Rules

Please be considerate of your neighbors and mindful of noise levels. Noise violations may result in fines. Please also note we do not provide speakers or sound systems.

Cancellation & Refund

to view the cancellation policy.

STR Permit No. n/a

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