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Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis

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Terrace/patio
Terrace/patio
Property grounds
Property grounds
Terrace/patio
6 bedrooms7 bathroomsSleeps 14

Popular amenities

  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning
£1,030
avg per night

Explore the area

View in a map
Annapolis, MD
  • Place, Bay Ridge Beach
    ‪4 min drive‬
  • Place, U.S. Naval Academy
    ‪11 min drive‬
  • Place, Chesapeake Bay Bridge
    ‪23 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪39 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

7 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

The current price is £1,030
avg per night

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About the area

Annapolis

Annapolis is home to this holiday home. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial 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.

What's nearby

  • Bay Ridge Beach - 4 min drive - 2.1 km
  • U.S. Naval Academy - 11 min drive - 6.9 km
  • Annapolis City Dock - 11 min drive - 6.9 km
  • Sandy Point State Park - 21 min drive - 20.0 km
  • Chesapeake Bay Bridge - 23 min drive - 22.1 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Bay Ridge Wine & Spirits - ‬5 min drive
  • ‪Boatyard Bar & Grill - ‬9 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬8 min drive

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.
Our prices include all fees. No hidden fees.

Amenities

Washing machine
Dryer
Pet-friendly
Air conditioning

House Rules

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

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed: dogs (limit 1 total)
default

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

Frequently asked questions

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

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

How much does it cost to stay at Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis?

As of 8 Mar 2026, prices found for a 1-night stay for 2 adults at Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis on 15 May 2026 start from £1,030, 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.

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?

Situated in Annapolis, this holiday home is within 1 mile (2 km) of Bay Ridge Beach, Chesapeake Bay and Northern Chesapeake Bay. Bay Bridge Market Place Shopping Center and Historic Mount Moriah AME Church are also within 3 miles (5 km).

Lakeside on the Chesapeake! Serene Waterfront home in charming Annapolis Reviews