Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Cottage in Annapolis, MD
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceOne of the higher cost properties in the area
About this cottage rental
Visit the magic of Annapolis during the Holiday Season
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 on the water of the Chesapeake Bay, at the mouth of the Severn River, the beautifully-landscaped property has incredible panoramic views. Located less than 15 minutes from downtown Annapolis (by boat or car) and equidistant to Navy-Marine Corps Memorial Stadium, the home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. 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
-Dogs allowed if $150 non-refundable pet fee per pet is paid prior to check-in.
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.
*If USNA cancels Graduation ceremonies, families will receive a full refund.
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 on the water of the Chesapeake Bay, at the mouth of the Severn River, the beautifully-landscaped property has incredible panoramic views. Located less than 15 minutes from downtown Annapolis (by boat or car) and equidistant to Navy-Marine Corps Memorial Stadium, the home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. 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
-Dogs allowed if $150 non-refundable pet fee per pet is paid prior to check-in.
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.
*If USNA cancels Graduation ceremonies, families will receive a full refund.
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Gym or Fitness Center
Garden
Map of Annapolis, MD
££££
Ratings and reviews
10.0 / 10.0
I actually grew up in Annapolis & spend many 4th of Julys on Bembe Beach. & remembered the view. So when it came time to get my parents & brothers together for a mini reunion, I knew just the spot. We all just sat in the backyard & enjoyed the view & paddle boarded & kayaked the majority of the time. The birds & boats & bridge make a fantastic backdrop. There is plenty of room to spread out & had everything we needed. We didn’t have to drive anywhere. We even got my favorite pizza “ Rocco’s “ delivered & walked to Port of Annapolis around the corner to go to my favorite bakery. If thinking about staying in Annapolis but don’t want to stay in the noisy downtown area, then Oh Happy Bay is the house for you. We can’t say enough. Great things about our stay ! We hope to make more memories there again next year.
10.0 / 10.0
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!
10.0 / 10.0
I needed a quiet place to rest and Oh Happy Bay was pperfectpabsolutely perfect. I was so impressed
10.0 / 10.0
Really like this place
10.0 / 10.0
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.
10.0 / 10.0
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
8.0 / 10.0
Kitchen was nice- well appointed. Love the little extras they provide. Home was cute. Ants were a big problem- and a lot of the outdoor furniture needs to be replaced- but the yard was great, and the view was lovely, It was quiet and beds were comfortable. Also great location.
10.0 / 10.0
Had a great weekend. Place was perfect for us.
10.0 / 10.0
We were in town for a wedding and had reserved Oh Happy Bay almost a year ago for the occasion. What a wonderful and relaxing home. The house is well appointed with all of the necessities plus most things you might have forgotten. We absolutely loved being able to put our toes in the bay from our own little beach. Sailboat watching was a favorite pastime. We discovered some delightful wildlife surprises in the immediate neighborhood; mallards, foxes with their kits playing and deer as well. We hope to have a need to come back to the area just so that we can stay here again!
10.0 / 10.0
Very well equipped kitchen. Nice and Clean. Spacious for entertaining. We had plenty of space to have six adult seniors for lunch one afternoon. Although weather was blustery and a bit rainy while we were there, and not much opportunity to spend time on the back porch, our stay was lovely. While the parking situation was a bit muddy, it wasn’t that inconvenient and certainly didn’t affect the wonderful features the home has to offer. A side note: I wouldn’t recommend for anyone with serious mobility issues because of the rocky parking and uneven stone walkway to the home.
10.0 / 10.0
Lovely, cozy cottage with everything we needed at a beautiful, peaceful location. Gorgeous views - loved the ducks and osprey hanging out in the yard. Also, very convenient to shopping, grocery stores and downtown Annapolis.
10.0 / 10.0
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!
6.0 / 10.0
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.
10.0 / 10.0
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.
10.0 / 10.0
Very family friendly with a cute little beach. Perfect get away place with lots of character.
10.0 / 10.0
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.
10.0 / 10.0
Our stay on the Bay was fantastic! My wife, daughter, and I needed time away as I finished my graduate degree this November. We were looking for a cozy cottage to hole up in for a week and just be at peace. We certainly found that!
10.0 / 10.0
The location is great. I would bring pots and pans. We went and bought some.
10.0 / 10.0
Our arrival was seamless and entry was easy, The house is terrific and the location is amazing! We are truly enjoying our time here!
10.0 / 10.0
Great location! Beautiful home!
10.0 / 10.0
Super clean and well furnished home with amazing waterfront views. Private beach, and kayak/paddle board access right on site. Owners and property manager were responsive and polite. Great stay!
10.0 / 10.0
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.
10.0 / 10.0
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!
10.0 / 10.0
Everything was perfect. You couldn’t Sk for a better home and location. The deer who visited us daily was an added touch!
10.0 / 10.0
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!
10.0 / 10.0
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.
10.0 / 10.0
"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!
10.0 / 10.0
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!!
FAQs
How much does this cottage cost compared to others in Annapolis?
The average price for a rental in Annapolis is £334 per night. This rental is £185 above the average.
Is parking included with this cottage?
Yes, parking is listed as an amenity at Waterfront dog-friendly home with beach just mins to Downtown Annapolis. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cottage?
We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.
Is Waterfront dog-friendly home with beach just mins to Downtown Annapolis pet friendly?
Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Waterfront dog-friendly home with beach just mins to Downtown Annapolis?
We found 11 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.
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