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Oh Happy Bay

Cottage in Annapolis, MD

8 guests·3 bedrooms·3 bathrooms
4.8 · 18 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Private beachfront access lets guests swim, paddle, and sunbathe daily.

Group & Family Friendly

Group & Family Friendly

Spacious family-friendly layout keeps extended groups connected and comfortable.

Entertainment & Amenities

Entertainment & Amenities

Gourmet kitchen and water-view dining elevate every vacation meal.

What guests are saying

Summarized with AI
Star icon

4.8

Rated 4.8 out of 5 from 18 reviews

Guests consistently praise this property for its breathtaking views and comfortable atmosphere, making them feel right at home. Many highlight the enjoyable beach experience, especially for families with children and pets. Reviewers commend the well-equipped house and its excellent location for water activities. Overall, this property stands out for its inviting ambiance and positive guest experiences, making it a favored choice for return visits.

See all 18 reviews.

Property details

Experience the Difference: Professionally Managed by the property manager 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. SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults: Upstairs Waterfront Bedroom: -King bed -Sitting room -Waterfront balcony -Queen air mattress available in the closet -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. Minimum age to book this property is : 25

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Queen Bed

Living Room

1 Sofa Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Wi-Fi

    Wi-Fi

Guest reviews

Star icon 4.8 | 18 reviews
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Theresa

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May 2026

GREAT location 5*! Beautiful views, quiet area, on the water, short drive to great shops, restaurants, live music, tours. Easy to find, easy entry, plenty of parking. Nice kitchen with all needed to prepare meals. Lacking basic expected items/amenities. Dining table is plenty big for all; board games. The family rm had plenty of seating although very dated, dingy, in need of replacement. The house has tons windows with a view!! Several screens were torn, many blinds didn't operate as they should-rods missing unable to open/close. Made it hard to get the view. The primary bedroom was very large! Great views; none of the linens were "luxurious"; the mattress has structural collapse/very uncomfortable/needs to be replace! Both bathrooms are in great need of gutting; the closet had 2 hangers(they did deliver move).

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Beth

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December 2025

The home was beautiful and welcoming. The bay view was gorgeous. I would definitely stay there again.

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Kevin And Lisa

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September 2025

The home is located in a very convenient and beautiful setting, overlooking the Annapolis harbor/bay. It has its own private beach, but lacks the appropriate and safe seating. The home is in serious need of maintenance and improvements. It is cozy, but is not safe in some areas of the outside porch, upstairs porch and ALL the windows and doors along with the screens for all, are in serious need of improvements and replacements (holes in most screens). The furniture is in need of some cleaning, as well. There is only one (1) TV in the home. The internet didn’t work for the first few days, and it took a communication technician to come into home at 8am to replace the outdated modem/router. This situation was known to the property manager before our arrival, but we never got that message. The showers (2) didn’t have any shower curtains and the showers and bathroom were not maintained properly. The property managers were responsive and apologetic. Regardless, we enjoyed our time.

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George

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August 2025

Classic beach house. A bit worn but clean and comfortable. Good beds, full kitchen, and great beach right on the bay.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 11:00am

Pets allowed

Min. age to rent: 25

No smoking

No parties

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