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Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis

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Terrace/patio - Lakeside on the Chesapeake!

Serene Waterfront home in charming Annapolis (Annapolis)
Iron/ironing board, Internet, bed sheets - Lakeside on the Chesapeake!

Serene Waterfront home in charming Annapolis (Annapolis)
Dining - Lakeside on the Chesapeake!

Serene Waterfront home in charming Annapolis (Annapolis)
Property grounds - Lakeside on the Chesapeake!

Serene Waterfront home in charming Annapolis (Annapolis)
Living area - Lakeside on the Chesapeake!

Serene Waterfront home in charming Annapolis (Annapolis)
Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis provides laundry facilities and more.

Popular amenities

  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning

Add dates for prices

About this property

Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis

  • Welcome to your private waterfront escape on Lake Ogleton, where relaxed luxury meets classic Chesapeake Bay living. This spacious home is designed for making memories, offering multiple indoor and outdoor gathering spaces, panoramic water views, and direct access to the Bay from your private deep-water dock (6.5+ ft).

    Outside, the property truly shines. Enjoy mornings by the water, afternoons in the hot tub, and evenings around the firepit surrounded by Adirondack chairs. The backyard features a large deck, a screened porch ideal for crab feasts and game nights, an outdoor Ping-Pong table, and a gas grill - perfect for entertaining family and friends. Boaters and water lovers will appreciate the private dock for crabbing, fishing, kayaking, jet skiing, sailing, or simply enjoying life on the Chesapeake.

    Inside, the main living room offers a comfortable and inviting space with expansive windows and sliding glass doors that open to the deck, filling the home with natural light and beautiful water views. A gas fireplace and entertainment system make this room a cozy spot to unwind after a day on the water. Just off the kitchen, the screened porch serves as a second living room with plush seating and a large dining table overlooking the lake.

    The home offers multiple additional living areas, giving everyone space to relax. The lower-level den includes a TV, games, a brand-new loveseat and sleeper sofa, and a full bathroom ideal for kids or extra guests. Upstairs, a bright sitting area with a futon couch/bed, table, chairs, and TV provides another comfortable retreat.

    The recently renovated kitchen is fully equipped for cooking and entertaining, featuring granite countertops, wood floors, a Viking oven and range, custom cabinetry, a built-in oversized refrigerator/freezer, and two large refrigerated drink drawers. A breakfast bar seats four, while the adjacent dining area offers an extra-long table for family meals. For alfresco dining, step directly onto the screened porch for meals with a view.

    Located near the Chesapeake Bay Foundation Trail and two miles of community beaches, this home offers easy access to biking, walking, and waterfront exploration all while remaining private and peaceful.

    Thoughtfully laid out, waterfront, and perfect for groups, this Lake Ogleton retreat is an ideal setting for a relaxing Chesapeake Bay getaway.

Property amenities

Internet

  • Available in the house: Internet access

Bedrooms

  • Bedsheets provided

Bathroom

  • Hair dryer
  • Soap
  • Toilet paper

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total pets

Children and extra beds

Children are welcome

Events

No events allowed

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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Bay Ridge, a neighbourhood in Annapolis, is home to this holiday home. Chesapeake Bay Bridge and Historical Society of Talbot County are local landmarks, and travellers looking to shop may want to visit Bay Bridge Market Place Shopping Center and Annapolis City Dock. Wild Bird Center and Annapolis Maritime Museum are also worth visiting. Visit our Annapolis travel guide
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Annapolis, MD

What's nearby

  • U.S. Naval Academy
    U.S. Naval Academy
    14 min drive - 8.6 km
  • Sandy Point State Park
    Sandy Point State Park
    28 min drive - 23.1 km
  • Chesapeake Bay Bridge
    Chesapeake Bay Bridge
    30 min drive - 25.2 km
  • Bay Ridge Beach
    3 min drive - 2.1 km
  • Annapolis City Dock
    15 min drive - 9.3 km

Getting around

  • Odenton Station
    27 min drive
  • Fort Meade, MD (FME-Tipton)
    36 min drive

Restaurants

  • McDonald's
    5 min drive
  • Boatyard Bar & Grill
    9 min drive
  • Sammy's Italian Pizza Kitchen
    8 min drive
  • Royal Farms
    9 min drive
  • Starbucks
    5 min drive

Frequently asked questions

Is Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis pet-friendly?

Yes, this property allows dogs (limit 1 total).

What time is check-in at Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis?

Check-in begins at 4:00 PM.

What time is check-out at Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis?

Checkout is at 11:00 AM.

Where is Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis located?

Located in Bay Ridge, this holiday home is within 1 mi (2 km) of Bay Ridge Beach and Chesapeake Bay. Northern Chesapeake Bay and Bay Bridge Market Place Shopping Center are also within 3 miles (5 km).

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