Located on the water's edge of Chesapeake Bay, Oh Happy Bay offers a serene retreat. Unwind in the beautifully landscaped backyard with its private beach, deck, and screened-in gazebo or enjoy panoramic views from the second-floor balcony. With a gourmet kitchen and high-speed internet access throughout your stay is sure to be relaxing.
Reviews
9.89.8 out of 10
Exceptional
Entire home
3 bedrooms2 bathroomsSleeps 8166 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Beachfront Home Minutes to Downtown Annapolis Dogs OK
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.
Property amenities
Beach
On the beach
Beach loungers
Beach towels
Internet
Available in the cottage: Free WiFi
Parking and transport
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Microwave
Oven
Paper towels
Refrigerator
Toaster
Dining
Dining table
Bedrooms
3 bedrooms
Bedsheets provided
Sofa bed
Bathroom
2 bathrooms
Bathtub or shower
Hair dryer
Outdoor shower
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Living room
Entertainment
Smart TV
Outdoor areas
Balcony
Barbecue grill
Garden
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Desk chair
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
Near the ocean
On the waterfront
Things to do
Boat
Paddleboard
Water sports equipment
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events allowed
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
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
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
About the area
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 Bay Bridge Market Place Shopping Center and Annapolis City Dock. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall. Visit our Annapolis travel guide
Is Beachfront Home Minutes to Downtown Annapolis Dogs OK pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Beachfront Home Minutes to Downtown Annapolis Dogs OK?
On-site parking is available at the property.
What time is check-in at Beachfront Home Minutes to Downtown Annapolis Dogs OK?
Check-in begins at 4:00 PM.
What time is check-out at Beachfront Home Minutes to Downtown Annapolis Dogs OK?
Checkout is at 11:00 AM.
Where is Beachfront Home Minutes to Downtown Annapolis Dogs OK 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).
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Beachfront Home Minutes to Downtown Annapolis Dogs OK Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers 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.
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!
Very family friendly with a cute little beach. Perfect get away place with lots of character.
Julie N.
Stayed 4 nights in Dec 2023
From a partner site
10/10 Excellent
D W.
30 Mar 2024
Perfect place to stay
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.
D W.
From a partner site
10/10 Excellent
Trish O.
14 Nov 2023
Great House
Our arrival was seamless and entry was easy, The house is terrific and the location is amazing! We are truly enjoying our time here!
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
From a partner site
10/10 Excellent
Hilary
25 Sept 2023
Hidden gem right by Annapolis!
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!
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.
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!
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.
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
From a partner site
8/10 Good
2 July 2024
Nice mini vacation
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.
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!
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.
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
From a partner site
10/10 Excellent
D S.
8 May 2024
Delightful surprise
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!
D S.
From a partner site
10/10 Excellent
james T.
25 Apr 2024
Equipped and Relaxing home
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.
james T.
Stayed 4 nights in Apr 2024
From a partner site
10/10 Excellent
5 Sept 2024
Location! Location! Location!
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.
Stayed 3 nights in Aug 2024
Verified
6/10 Okay
MAGGIE B.
8 Mar 2024
Liked: Cleanliness, check-in, communication
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.
We absolutely loved this house and would love to book again. The little sandy beach was perfect for our granddaughter, the screened-in gazebo with large table was great for picking crabs, and the view from the primary bedroom upstairs was spectacular. The house was clean, comfy, and well stocked. A little gem!