Entire home

Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views

Photo gallery for Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views

Living area
Living area
Room
Room
Living area
4 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View map
Saint Leonard, MD
  • Place, Matoaka Beach
    ‪6 min walk‬
  • Place, Flag Harbor Marina
    ‪9 min walk‬
  • Place, Flag Ponds Nature Park
    ‪18 min walk‬

Rooms & beds

4 bedrooms (sleeps 10)

Downstairs Bedroom 4

1 King Bed

Upstairs Bedroom Bunkroom

2 Single Bunk Beds

Upstairs Bedroom with Sunroom

1 Queen Bed

Upstairs Primary Bedroom Suite

1 King Bed

3 bathrooms

Downstairs Bathroom

Towels provided · Bathtub or shower · Toilet · Shower only

Primary Suite Bath

+1
Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Jetted bathtub · Hair dryer

Upstairs Hall Bathroom

Towels provided · Bathtub or shower · Bathtub · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Garden

About this property

Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views

No Bay Bridge traffic, no MD/DE beach crowds. Just a private 1-mile beach, panoramic Chesapeake Bay views, and a cliffside home built for unplugging — with fast WiFi when you need it. Close enough to DC to be spontaneous — far enough to feel like a world away. Calvert County’s best kept secret.
The water here is shallow and usually calm — perfect for wading, exploring, and letting kids play without worrying about big waves. The private community beach is reserved for residents only, never gets crowded, and is one of the Chesapeake’s best-known stretches for shark tooth and fossil hunting. Walk the full mile of shoreline, launch kayaks or paddleboards from the shore, fish, swim, or simply stroll in the quiet.
The natural world here is genuinely remarkable. Daily visitors include osprey diving for fish, bald eagles soaring overhead, great blue herons stalking the shoreline, and bay birds throughout the property. Discover horseshoe crabs and blue crabs along the shore. In summer, you might even spot dolphins or sea turtles out in the bay. It’s the kind of place that turns non-nature people into nature people.
This recently renovated 4BR/3BA home sleeps 8 and is thoughtfully designed for multi-family or multigenerational groups — two fully separate living spaces mean everyone has room to spread out.
The upper level features bay views from the living rooms, dining room, kitchen, two sunrooms, and covered deck balcony. One living room has a deep-seated sofa and 42” smart TV; the other is floor-to-ceiling windows facing the water. The primary suite has a king bed, oversized shower, and air jet soaking tub. A second bedroom has a queen with its own private sunroom. A third has two bunk beds sleeping 4. Dining for 6, bar seating for 3.
The lower level is a destination in itself — sectional sofa, two spinning barrel chairs, 70” smart TV, foosball, pop-a-shot basketball, dining table for 4, kitchenette with full-sized fridge and wet bar, kids play area, and a private king bedroom and full bath with direct walk-out access to the covered patio and outdoor dining for 6.
Throughout the home: ambient cove ceiling lighting and dimmer switches in every room, ceiling fans in all bedrooms, and floor heaters in all 3 bathrooms. The kind of details you notice and appreciate.
Fully stocked kitchen. Fast WiFi. 5 parking spaces across 2 driveways. Come unplug.

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
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

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
Long-term renters welcome
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

St. Leonard

St. Leonard is home to this holiday home. The area's natural beauty can be seen at Chesapeake Bay and Battle Creek Cypress Swamp Sanctuary, while calvART Gallery and Calvert Marine Museum are cultural highlights. R&J's PlayPark and Kocen Arts Center are also worth visiting.
Map
Saint Leonard, MD

What's nearby

  • Matoaka Beach - 6 min walk - 0.6 km
  • Flag Harbor Marina - 9 min walk - 0.8 km
  • Flag Ponds Nature Park - 18 min walk - 1.6 km
  • Calvert Cliffs State Park - 15 min drive - 16.8 km
  • Patuxent River Naval Air Station - 44 min drive - 43.4 km

Restaurants

  • ‪Linda's Produce Stand - ‬9 min drive
  • ‪Vera's White Sands Beach Club - ‬16 min drive
  • ‪Frying Pan - ‬13 min drive
  • ‪Adam's The Place For Ribs - ‬10 min drive
  • ‪The Tavern - ‬4 min drive

Frequently asked questions

Is Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views pet-friendly?

No, pets are not allowed at this property.

How much is parking at Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views?

On-site parking is available at the property.

What time is check-in at Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views?

Check-in begins at 3:00 PM.

What time is check-out at Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views?

Checkout is at 11:00 AM.

Where is Cliffside Bay Home · Private Beach, Shark Tooth Hunting & Panoramic Bay Views located?

Situated in St. Leonard, this holiday home is steps away from Northern Chesapeake Bay and Chesapeake Bay. Matoaka Beach and Long Beach are also within 15 minutes.

About the host

Hosted by Rachel

Host profile image

Why they chose this property

Located along the western shore of the Chesapeake Bay, Calvert Beach is a quiet, laid-back waterfront community known for its natural beauty and peaceful setting. Residents and guests enjoy access to a private community beach with sandy shoreline and gentle bay waters—perfect for swimming, kayaking, paddle boarding, or simply relaxing by the water.

The beach is also well known for fossil hunting, where it’s common to find shark teeth and other unique treasures along the shoreline. The surrounding area offers a true nature-focused experience, with frequent sightings of birds and marine life.

Just minutes away is St. Leonard, where you’ll find small local markets, casual dining options, and everyday essentials. Nearby marinas provide convenient access for boating, fishing, and waterfront recreation, making it easy to enjoy everything the Chesapeake Bay lifestyle has to offer.

What makes this property unique

What I love most about this home is how easy it is to truly unplug without going far. It’s become a go-to retreat for me and my family—a peaceful escape from the city that’s still close to the DC metro area, without the long drive to Ocean City or dealing with Bay Bridge traffic.

The water here is usually calm and shallow, which makes it perfect for wading, exploring, and letting kids play without worrying about big waves. The beach is great for long walks, fossil hunting, or just enjoying the quiet shoreline.

The setting of the home itself is something special—perched up on a cliff, the views are completely panoramic across the bay. You can enjoy them from inside year-round, whether you’re relaxing in the living room or having your morning coffee. The sunrises are breathtaking as the sun rises across the bay, and the sunsets create beautiful, colorful evening skies.

It’s incredibly quiet, comfortable, and surrounded by nature. One of my favorite things is simply watching the wildlife—birds flying overhead, activity in the water, and the ever-changing scenery. It’s a place that naturally helps you slow down and reset.

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