A rare beachfront property in the area - enjoy direct access to the sand and sea.
At the center of it all
Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
Discover nearby landmarks
Near Annapolis Landing Marina
3 bedrooms2+ bathroomsSleeps 8
Popular amenities
On beach
Onsite parking available
Pet-friendly
Kitchen
Washing machine
Air-conditioning
Explore the area
Annapolis, MD
Annapolis Sailing School
Place, Annapolis Sailing School
3 min walk
Annapolis Landing Marina
Place, Annapolis Landing Marina
11 min walk
Sparrows Beach
Place, Sparrows Beach
19 min walk
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
55 min drive
Rooms & beds
3 bedrooms (sleeps 8)
Family Room
1 Double Sofa Bed
Main floor
1 Queen Bed
Upstairs Queen
1 Double Bed
Waterfront King
1 King Bed
2 bathrooms, 1 half bathroom
2nd Floor Hall Bath
Bathtub · Toilet · Shower only
Main Floor Full Bath
Bathtub or shower · Toilet
Outside Shower
Outdoor shower
Spaces
Deck or patio
Outdoor shower
Kitchen
Balcony
Number of living rooms
Garden
About this property
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Experience the Difference: Professionally Managed by iTrip Annapolis
Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show.
The home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay).
Head back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer.
The home has plenty of parking and space to explore with the pups and little family members.
Located walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away.
-Shared bathroom with stand-up shower and soaking tub
-Flatscreen TV
Guest Bedroom across the hall from King Bedroom:
-Full bed
-Shared bathroom with stand-up shower and soaking tub
Main Floor Bedroom:
-Queen bed
-Full hall bath in the hall with stand-up shower
Family Room
-Full Sleeper Sofa
-Full hall bath with stand-up shower
HIGHLIGHTS:
-Private beach with access to Chesapeake Bay
-Screened-in patio gazebo with dining table for 10
-Back deck with seating, picnic table and beachside seating
-Charcoal BBQ grill
-Gourmet kitchen
-Dining room table seats 6-8
-High Speed Internet and WiFi
-Big Flatscreen TV
-Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October)
-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
-Outdoor shower
-Parking for multiple cars in driveway and on street
-Full Laundry room with washer & dryer located inside the home
Property Distance to:
-Downtown Annapolis – 4 miles
-U.S. Naval Academy – 4.5 miles
-Washington, DC – 34 miles
-Baltimore - 35 miles
* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are made for you with freshly-laundered sheets & towels.
House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents, the neighbors and neighborhood.
Our prices include all fees. No hidden fees.
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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.
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
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
Annapolis
Located in Annapolis, this cottage is on the beach. Wild Bird Center and Annapolis Maritime Museum are local attractions and those in the mood for shopping can visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
Is Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?
As of 18 Aug 2026, prices found for a 1-night stay for 2 adults at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly on 10 May 2027 start from £1,408, 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 Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?
On-site parking is available at the property.
What time is check-in at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?
Check-in begins at 4:00 PM.
What time is check-out at Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly?
Checkout is at 11:00 AM.
Where is Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly located?
Nestled on the beach, this Annapolis cottage is within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina. Sparrows Beach and Carrs Beach are also within 3 miles (5 km).
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests