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This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.

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Outdoor dining
Main photo
Interior
Living area
Living area
5 bedrooms5+ bathroomsSleeps 145922 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Annapolis, MD
  • Place, Bay Ridge Beach
    ‪5 min walk‬
  • Place, U.S. Naval Academy
    ‪13 min drive‬
  • Place, Annapolis City Dock
    ‪13 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪42 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

King Suite

1 King Bed

King Suite

1 King Bed

King Suite

1 King Bed

King Suite with Two Twins

2 Twin Beds and 1 King Bed

Two Queen Suite Bedroom

2 Queen Beds

5 bathrooms, 1 half bathroom

Ensuite Bedroom #2

Bathtub or shower · Toilet

Ensuite Bedroom #3

Bathtub or shower · Toilet

Ensuite Bedroom #4

Bathtub or shower · Toilet

Ensuite Bedroom #5

Bathtub · Toilet · Shower only

Ensuite to Bedroom #1

Bathtub or shower · Toilet

Main Level

Toilet

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.

Welcome to Ogelton Overlook. This 5 bedroom / 5 bathroom Coastal Charm sleeps 14 comfortably. This thoughtfully stylish home overlooks the Bay and is your perfect Annapolis escape.
Nestled in a charming coastal neighborhood, this beautifully located home offers the perfect blend of relaxation, comfort, and classic Chesapeake Bay charm. Whether you're visiting for sailing, a weekend getaway, Naval Academy events, or simply to explore the historic waterfront, this home puts you right in the heart of it all. Step inside and feel instantly at home in a bright, welcoming space designed for comfort and relaxation. This inviting property offers the perfect setting for families, couples, and groups looking to experience Annapolis like a local.

Guests love the mix of comfortable living spaces perfect for relaxing after a day on the water. Thoughtfully designed interiors with coastal-inspired touches
Plenty of room to unwind, connect, and make memories. Whether you're enjoying morning coffee before a day of sailing or relaxing after exploring downtown, this home offers the ideal home base. Additionally, you'll have easy access to downtown Annapolis, a quiet neighborhood feel while staying close to everything and a relaxing place to unwind after a day of exploring.
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During your stay you'll be minutes from; the Historic downtown waterfront full of Sailing, Marinas, and Chesapeake Bay views. The local flavor full of incredible seafood restaurants and waterfront dining. Local boutiques for shopping, town favorite coffee shops, and art galleries. Naval Academy events and campus visits.

Spend your day exploring cobblestone streets, watching boats glide across the harbor, or enjoying famous Maryland crab cakes before returning to your peaceful retreat.
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We want every guest to have a 5-star stay. You'll enjoy:
Easy self check-in
Clear communication
Local recommendations
A clean, comfortable home prepared for your arrival

​​​​​​Book now and experience the charm, history, and coastal beauty of Annapolis from your own private retreat.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Free WiFi
Air conditioning
Outdoor Space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Annapolis

Located in Annapolis, this vacation home is on the waterfront. Chesapeake Bay Bridge and Historical Society of Talbot County are local landmarks, and the area's natural beauty can be seen at Chesapeake Bay and Jonas Green State Park. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
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Map
Annapolis, MD

What's nearby

  • Bay Ridge Beach - 5 min walk - 0.4 km
  • U.S. Naval Academy - 13 min drive - 8.9 km
  • Annapolis City Dock - 13 min drive - 8.9 km
  • Sandy Point State Park - 24 min drive - 22.0 km
  • Chesapeake Bay Bridge - 26 min drive - 24.1 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 38 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪Carrol's Creek Cafe - ‬11 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬9 min drive
  • ‪Boatyard Bar & Grill - ‬11 min drive
  • ‪Royal Farms - ‬10 min drive

Frequently asked questions

Is This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape. pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.?

As of Apr 25, 2026, prices found for a 1-night stay for 2 adults at This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape. on Jun 21, 2026 start from $1,653, 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?

Onsite parking is available at the property.

What time is check-in at This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.?

Check-in begins at 4:00 PM.

What time is check-out at This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape.?

Check-out is at 10:00 AM.

Where is This thoughtfully styled home overlooks the Bay and is perfect for your Annapolis escape. located?

Situated on the waterfront, this vacation home is within a 5-minute walk of Chesapeake Bay, Northern Chesapeake Bay, and Bay Ridge Beach. Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park are also within 3 mi (5 km).

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