Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
36 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 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.
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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 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.
Is Beachfront Home Minutes to Downtown Annapolis Dogs OK pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Beachfront Home Minutes to Downtown Annapolis Dogs OK?
As of 16 Apr, 2026, prices found for a 1-night stay for 2 adults at Beachfront Home Minutes to Downtown Annapolis Dogs OK on 24 May, 2026 start from S$987, 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 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).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Excellent location for a relaxing weekend with our dogs and midshipman!
Celine D.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 1 Oct, 2025
Thanks, Celine! We’re thrilled to hear that Oh Happy Bay was excellent for your relaxing weekend. It’s wonderful to know that the location was perfect for you, your dogs, and your midshipman. We’re glad you enjoyed your time with us and would love to host you again next time you’re in town.
Melissa~iTrip Annapolis
Amazing views with great amenities. I prefer no pets and wasn’t aware it was pet friendly.
Joni K.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 4 Nov, 2025
Thanks, Joni! We’re delighted to hear that Oh Happy Bay provided amazing views and great amenities for you. We hope to have the opportunity to host you again!
Melissa~iTrip Annapolis
From a partner site
8/10 Good
Chris L.
12 Aug, 2025
Weekend trip
Great waterfront location, with nice beach and waterside screened porch-perfect for dinning.
Chris L.
Response from VrboOwner on 14 Aug, 2025
Thanks, Chris! We’re thrilled to hear that Oh Happy Bay was a great waterfront location and that you enjoyed the nice beach and waterside screened porch for dining. We would love to host you again next time you’re here.
Melissa~iTrip Annapolis
From a partner site
10/10 Excellent
Shelley K.
9 Sept, 2025
Comfort Right on the Water
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!
Shelley K.
Response from VrboOwner on 13 Sept, 2025
Thanks, Shelley! We’re thrilled to hear that Oh Happy Bay was perfect for your stay. It’s wonderful to know that you and your family enjoyed the little sandy beach, the screened-in gazebo for picking crabs, and the spectacular view from the primary bedroom. We’re delighted that you found the house clean, comfy, and well stocked. We would love to host you again next time you’re in town.
Melissa~iTrip Annapolis
Everything was great. House and proximity to the water were tremendous. Only difficulty was the access to the water taxi. The water taxi stops near the house were either closed or harder to get to than expected.
Jeffrey M.
Stayed 2 nights in Sep 2025
Response from VrboOwner on 19 Sept, 2025
Thanks, Jeffrey! We’re thrilled to hear that Oh Happy Bay was perfect for your stay. It’s wonderful to know that you enjoyed the house and its proximity to the water. We apologize for the inconvenience with the water taxi access and appreciate your feedback. We would love to host you again next time you’re in town.
Melissa~iTrip Annapolis
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
Response from VrboOwner on 3 Jun, 2025
Hi Anthony! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
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
Response from VrboOwner on 11 Nov, 2024
Hi Elizabeth! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
Very family friendly with a cute little beach. Perfect get away place with lots of character.
Julie N.
Stayed 4 nights in Dec 2023
Response from VrboOwner on 4 Jan, 2024
Thanks, Julie. We would love to host you again - please reach out next time you’re planning another trip to Annapolis.
Sean, iTrip Annapolis
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.
Response from VrboOwner on 30 Mar, 2024
Thank you for allowing us to host your stay Nicole & we welcome you back anytime! Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Jonathan H.
24 Jun, 2025
Great Last Minute Get Away!
We were looking for a house with a private beach that felt private and was close to amenities. This house made our vacation very fun and special. The house had stand up paddle boards and a kayak, a hammock and plenty of things that us outdoor folks love to use right on the water. The private beach was perfect and beautiful, especially for sunrise. The kitchen we well stocked and there was enough room for each one in the family to have their own space. We would definitely return for a future getaway!
Jonathan H.
Response from VrboOwner on 26 Jun, 2025
Thanks, Jonathan! We’re thrilled to hear you enjoyed your stay at Oh Happy Bay and appreciated the private beach and outdoor amenities. It sounds like you had a wonderful time! We’d love to host you again anytime you’re back for another getaway! Melissa~iTrip Annapolis
Wonderful stay! Amazing private beach on the mouth of the Severn that is waist deep water, our whole family had a blast! We enjoyed swimming, paddle boarding, etc.. We would definitely come back! Unfortunately you're not able to take a water taxi directly from the property, you have to walk over to a nearby marina. They also only pick up one time per hour as an FYI so it's not the most convenient way to get downtown. I would definitely recommend the house, everything was clean and it was nice they had SUP and a Canoe for use.
Scott A.
Stayed 2 nights in Aug 2025
Response from VrboOwner on 29 Aug, 2025
Thanks, Scott! We’re thrilled to hear that Oh Happy Bay was a wonderful stay for your family. It’s We’re glad you found everything clean and appreciated the availability of the SUP and Canoe. We understand the water taxi situation and appreciate your feedback on that. We would love to host you again next time you’re in town!
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
Response from VrboOwner on 3 Aug, 2023
Thank you Leslie for your kind review of Oh Happy Bay. We are pleased to hear you enjoyed your stay. We hope to have the opportunity to host you again. Safe Travels!
-Tiffany
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!
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
Response from VrboOwner on 3 Jun, 2025
Hi Kristin! Thank you for allowing us to host your stay & we are thrilled to know you enjoyed your time in the home! We welcome you back anytime, Melissa~iTripAnnapolis
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
Response from VrboOwner on 3 Sept, 2024
Hi Marianne! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
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
Response from VrboOwner on 25 Mar, 2024
Thanks, Monica! We look forward to hosting you again next year.
Sean, iTrip Annapolis
From a partner site
10/10 Excellent
kim m.
3 Jul, 2023
Great stay by the bay!
Everything was perfect. You couldn’t Sk for a better home and location. The deer who visited us daily was an added touch!
kim m.
Stayed 6 nights in Jun 2023
Response from VrboOwner on 24 Oct, 2023
Thanks, Kim! Please come back and stay with us again any time.
Sean
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!
Hilary
Response from VrboOwner on 24 Oct, 2023
Thanks, Hilary, for the great feedback. Come back and stay with us again any time!
Sean
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
Response from VrboOwner on 29 Feb, 2024
Thank you Penny for allowing us to host your stay & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
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
Response from VrboOwner on 2 Jan, 2024
Thanks, Denise. We welcome you and your dog back any time!
Sean, iTrip Annapolis
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
Response from VrboOwner on 16 Jul, 2024
Hi Bryan! Thank you for allowing us to host your stay & for sharing your positive stay experience! We welcome you back anytime, Melissa~iTripAnnapolis
From a partner site
10/10 Excellent
Joseph F.
18 Dec, 2023
Needed Time Away
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!
Joseph F.
Stayed 3 nights in Dec 2023
Response from VrboOwner on 18 Dec, 2023
Thank you, Joseph! So glad you enjoyed Oh Happy Bay! Please come back and stay with us again any time.
Sean
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests