On the beach.At this cottage, you'll be steps from Annapolis Sailing School and within a 10-minute walk of Annapolis Landing Marina. Sparrows Beach and Bay Bridge Market Place Shopping Center are also within 3 miles (5 km).
Annapolis Maritime Museum - 8 min walk - 0.5 miles
Annapolis City Dock - 4 min drive - 1.7 miles
U.S. Naval Academy - 5 min drive - 1.5 miles
Navy-Marine Corps Memorial Stadium - 6 min drive - 3.0 miles
Getting around
Odenton Station - 29 min drive
Fort Meade, MD (FME-Tipton) - 31 min drive
Restaurants
The Choptank - 10 min drive
O'Brien's Annapolis' Original Steakhouse - 10 min drive
Chipotle Mexican Grill - 10 min drive
Boatyard Bar & Grill - 9 min drive
Pusser's Caribbean Grille - 10 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
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.
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.
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
General
Garden
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
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
Pets
Pets are welcome
Service animals are exempt from fees
Children and extra beds
Children are welcome.
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. Onsite parties or group events are strictly prohibited.
Property is also known as
12207
Frequently asked questions
How close is Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK to the airport?
This cottage is 22.9 mi (31-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.
Does Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK have an airport shuttle?
Airport shuttle services are not available at this cottage.
How close is Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK to the beach?
This cottage is on the beach. Don't forget your sunscreen!
Does Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK offer free breakfast?
This cottage does not offer free breakfast.
Is there a casino at Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK?
No, there is no casino at this cottage.
What time is check-in at Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK?
Check-in begins at 4:00 PM.
Is there free parking at Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK?
Free parking is not available at this cottage.
Does Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK have a pool?
This cottage does not have a pool.
Does Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK have a spa?
There are no spa services available at this cottage.
How close is Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK to downtown Annapolis?
This cottage is 1.3 mi away from Annapolis.
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 30 out of 32 reviews
10 - Excellent
30
Rating 8 - Good. 1 out of 32 reviews
8 - Good
1
Rating 6 - Okay. 1 out of 32 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 32 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 32 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
10/10 Excellent
Anthony L.
May 18, 2025
Liked: Cleanliness
Incredible stay
We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting.
Anthony L.
Stayed 2 nights in May 2025
10/10 Excellent
K- M., San Diego, CA United States
May 5, 2025
Liked: Cleanliness
Perfect for Quality Family Time
Everyone in the family who stayed here loved it -- all ages! The open floor plan made spending time together inside easy and there was also enough space when we were sitting outside watching the sailboats and listening to the water hit the sandy beach. The house is well equipped (dishes, glasses, silverware, living room seating, big dining room table, sheets and towels) and we found it much cleaner than other homes we've stayed. And it's dog friendly! The house is on a quiet street almost at the end of the road, so peaceful. We truly enjoyed the week we spent here!
K- M.
Stayed 7 nights in Apr 2025
10/10 Excellent
Elizabeth K.
Sep 28, 2024
Liked: Cleanliness
Absolutely lovely Beachside getaway
My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!
Elizabeth K.
Stayed 6 nights in Sep 2024
10/10 Excellent
Marianne B.
Aug 27, 2024
Liked: Cleanliness
Heavenly Haven
I needed a quiet place to rest and Oh Happy Bay was pperfectpabsolutely perfect. I was so impressed
Marianne B.
Stayed 3 nights in Aug 2024
10/10 Excellent
Juanita D.
Aug 27, 2024
Liked: Cleanliness
A great stay at Oh Happy Bay!
A beautiful home right on the bay! We enjoyed watching the sunrise, the sailboats, swimming, paddleboards, bike riding and the outdoor spaces. The kitchen and baths were updated. Short drive to downtown and close to supermarket and Rx. Hosts were easy to contact and communicate with. Would definitely return!
Juanita D.
Stayed 4 nights in Aug 2024
10/10 Excellent
SCOTT B.
Aug 16, 2024
Liked: Cleanliness
Great place
Really like this place
SCOTT B.
Stayed 4 nights in Aug 2024
10/10 Excellent
Courtney M.
Aug 13, 2024
Liked: Cleanliness
Beautiful location
The location was amazing. It’s right on the water and close to downtown Annapolis. We all enjoyed a couple days of relaxing near the water and the kids LOVED the paddle boards and Kayaks. The adults loved watching the sailboats and other boats go by.
Our only complaint is the couches and outside furniture could be updated but it wouldn’t be a deal breaker for us staying again. The kitchen had everything we needed to cook meals.
We enjoyed our stay and hope to come back again.
Courtney M.
Stayed 5 nights in Aug 2024
10/10 Excellent
Bryan B.
Jul 6, 2024
Liked: Cleanliness
Family vacation
Nice atmosphere for the family to enjoy comfortably. Private beach was nice since had a grandchild under 2. She loved playing in the sand with everyone. Sleeping areas were great. Master bedroom was outstanding with a great view of the bay. Plenty of amenities to keep the family busy
Bryan B.
Stayed 4 nights in Jul 2024
10/10 Excellent
Thomas C., Pittsford
Jul 1, 2024
Liked: Cleanliness
Sailing Weekend.
Had a great weekend. Place was perfect for us.
Thomas C.
Stayed 4 nights in Jun 2024
10/10 Excellent
Monica M.
Mar 17, 2024
Liked: Cleanliness
Cousins Trip to Chesapeake Bay
The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!
Monica M.
Stayed 2 nights in Mar 2024
6/10 Okay
MAGGIE B.
Mar 8, 2024
Liked: Cleanliness
Inconvenient access
This trip was created for siblings to get together. In the listing, I believe it said there was a driveway and it showed a nice entryway. However, there was no driveway. You had to park across the other side of the road in front of the cottage. And all that was there was rocks and dirt. The walkway from, the strip of rocks for the car was all dirt and mud because it had been raining. There should be either a paved area or enough rocks and gravel that you don’t get dirt mud all over you. There was nowhere to go to avoid it. They had a few slate rocks on one section , but that was after you had to walk through a long strip of mud. An area could easily be made into a driveway and be paved. We have a handicap sister, who had extreme issues getting back-and-forth from the car to the house. One of the sofas and and a chair in the living room were completely shot. You don’t need anything fancy in a rental but something that is not completely collapsed and has no support left is really uncomfortable. The dining tables and chairs were fine. The kitchen was very nice. The upstairs loft master bedroom with the sitting area was beautiful as was the bathroom up there. It’s a shame the rest of the house could not compete. The back deck area and top balcony had a lot of green fungus and should have been be wiped between guests. Carpenter ants were all around inside. So nice water view but lacking.
MAGGIE B.
Stayed 5 nights in Mar 2024
10/10 Excellent
Penny B.
Feb 28, 2024
Liked: Cleanliness
Rest & relaxation getaway
We had a great extended weekend here! The weather and scenery were perfect for some needed R&R with friends. The house was cozy and clean, and we really enjoyed the quiet, lovely location. It was close to everything and also an escape from the hustle and bustle.
Penny B.
Stayed 3 nights in Feb 2024
10/10 Excellent
Julie N.
Jan 4, 2024
Liked: Cleanliness
Absolutely beautiful
Very family friendly with a cute little beach. Perfect get away place with lots of character.
Julie N.
Stayed 4 nights in Dec 2023
10/10 Excellent
Denise W.
Jan 2, 2024
Liked: Cleanliness
Christmas trip
We enjoyed a Christmas away from home at this lovely property. We were so happy with our stay! The home was even better than we expected. It was warm and well cared for. The view was amazing. Our dog loved swimming in the bay. We will definitely stay again.
Denise W.
Stayed 4 nights in Dec 2023
10/10 Excellent
David C.
Nov 29, 2023
Liked: Cleanliness
The View
The location is great. I would bring pots and pans. We went and bought some.
David C.
Stayed 5 nights in Nov 2023
10/10 Excellent
Lisa R.
Oct 13, 2023
Liked: Cleanliness
Wonderful stay!
Great location! Beautiful home!
Lisa R.
Stayed 2 nights in Oct 2023
10/10 Excellent
Richard T.
Sep 12, 2023
Liked: Cleanliness
Yes Happy Bay
The house was clean and spacious, the kitchen well stocked with cookware and appliances. The best part was the private sandy beach just steps from the back door. The adults, kids and dog all loved playing in the calm bay water. The neighborhood was quiet and pleasant with a nice bakery in walking distance.
Richard T.
Stayed 3 nights in Sep 2023
10/10 Excellent
Leslie C.
Jul 14, 2023
Liked: Cleanliness
Week in Annapolis
We had an amazing time this week! Would book this place again and hopefully will have the chance to do so. Very comfortable and absolutely fantastic location!
Leslie C.
Stayed 5 nights in Jul 2023
10/10 Excellent
Therese G.
May 7, 2023
Liked: Cleanliness
Perfect
Oh Happy Bay was certainly that. A charming cottage, well equipped, right on the bay with lovely views of sail boats passing by. Ample parking, comfy beds, beautiful sunrises and sunsets. Perfect!
Therese G.
Stayed 14 nights in Apr 2023
10/10 Excellent
Audrey H.
Apr 23, 2023
Liked: Cleanliness
This was the perfect meetup for myself, my daughter and two granddaughters.
We really enjoyed the property with all its appeal, the beach, sunrise, comfort, quiet. It is in close driving proximity to downtown Annapolis where we spent the day enjoying a boat tour and shopping. Everything was up to par in the listing if not better.
Audrey H.
Stayed 3 nights in Apr 2023
10/10 Excellent
Amy P.
Apr 14, 2023
Liked: Cleanliness
Perfect Vacation Spot on the Bay
"Oh Happy Bay" could not have been a more perfect spot for our weekend trip to Annapolis. There was plenty of room for all 4 of the adults visiting. The pictures can't do justice to how special this location is. The water is right out the backdoor and the yard is appointed in a way to allow multiple spots to sit and relax.
The home was absolutely beautiful. There is tons of natural light and the furnishings in every room make it comfortable. Literally at every turn there was a special extra touch.
Thank you to Sean for a top tier stay. Accommodations and extra touches were so appreciated and the check-in and check-out was seamless and easy. Thank you also to Cathy for timely communications and answering any questions we had.
We could not have been happier with our stay - it was the perfect way to celebrate my Dad's birthday. The entire family plans to stay here again! Highly recommend!
Amy P.
Stayed 3 nights in Apr 2023
10/10 Excellent
robin h.
Mar 31, 2023
Liked: Cleanliness
Great stay
Had a lovely stay at Oh Happy Bay! Very comfortable home in a beautiful location. Well stocked kitchen for everything you could ever need. Super clean and comfortable for the entire family. Gorgeous sunrise views over the bay. Husband enjoyed a nice paddle out on the bay. Quick drive to DTA. Tons of fluffy towels always a bonus!!