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Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

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A large, two-story house with a spacious front yard and a driveway leading to the entrance.
A spacious dining area with a glass table and leather chairs, large windows with ocean views, and a modern interior design.
A patio with Adirondack chairs and a fire pit overlooking a body of water and a pier.
A spacious lobby with a glass wall leading to a lush indoor garden, wooden flooring, and a modern reception desk.
A spacious kitchen with stone walls, a large island, and a view of trees.

Reviews

9.8 out of 10
Exceptional
7 bedrooms6 bathroomsSleeps 16

Popular amenities

  • On beach
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Dameron, MD
  • Place, Saint Jerome Beach
    ‪9 min walk‬
  • Place, St. Mary's College of Maryland
    ‪18 min drive‬
  • Place, Point Lookout State Park
    ‪19 min drive‬

Rooms & beds

7 bedrooms (sleeps 16)

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Queen Beds

Bedroom 5

1 King Bed

Bedroom 6 (Cottage)

2 Queen Beds

Bedroom 7 (Cottage)

1 Double Bed

Primary Bedroom

1 King Bed

6 bathrooms

Ensuite Bathroom 1

Bathtub · Toilet · Shower only

Ensuite Bathroom 2

Toilet · Shower only

Ensuite Bathroom 3

Toilet · Shower only

Ensuite Bathroom 4

Ensuite Bathroom 5

Ensuite Bathroom 6

Spaces

Deck or patio
Kitchen
Office
Garden
Dining area

About this property

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

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 AvantStay's 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.

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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

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This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

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 AvantStay 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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3734494vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Dameron

Located in Dameron, this holiday home is on the beach. Chesapeake Bay and Saint Inigoes State Forest reflect the area's natural beauty and area attractions include Montgomery Hall Fine Arts Center and Michael P. O'Brien Athletics and Recreation Center.
Map
Dameron, MD

What's nearby

  • Saint Jerome Beach - 9 min walk - 0.8 km
  • St. Mary's College of Maryland - 18 min drive - 18.8 km
  • Point Lookout State Park - 19 min drive - 21.8 km
  • Patuxent River Naval Air Station - 24 min drive - 29.3 km
  • Calvert Cliffs State Park - 50 min drive - 54.5 km

Restaurants

  • ‪St. James Deli - ‬13 min drive
  • ‪SALT Waterfront Kitchen - ‬16 min drive
  • ‪Pier450 - POV Restaurant - ‬16 min drive
  • ‪St Michaels Knights Of Columbus Hall Ridge Md - ‬12 min drive
  • ‪Circle C. Oyster Ranchers Association , Ridge , MD - ‬17 min drive

Frequently asked questions

Is Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay?

As of 19 Aug, 2026, prices found for a 1-night stay for 2 adults at Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay on 20 Dec, 2026 start from S$4,186, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay?

On-site parking is available at the property.

What time is check-in at Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay?

Check-in begins at 4:00 PM.

What time is check-out at Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay?

Checkout is at 11:00 AM.

Where is Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay located?

Nestled on the beach, this Dameron holiday home is within a 10-minute walk of Chesapeake Bay and Saint Jerome Beach. Elms Beach Park and First District Community Park are also within 9 miles (15 km).

About the host

Hosted by AvantStay

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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