Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis, Maryland
$1077 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

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.



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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Beach Sun Loungers Beach Towels On The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 1784 Sq Ft (166 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden Outdoor Furniture
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Boat On Site Paddleboard On Site Water Sports Equipment
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    Near The Ocean On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Availability

Review Review

  • Joni K.

    Submitted Oct 27, 2025

    Stayed Oct 25, 2025

    Amazing views with great amenities. I prefer no pets and wasn’t aware it was pet friendly.

  • Celine D.

    Submitted Sep 30, 2025

    Stayed Sep 26, 2025

    Excellent location for a relaxing weekend with our dogs and midshipman!

  • Jeffrey M.

    Submitted Sep 14, 2025

    Stayed Sep 12, 2025

    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.

  • Shelley K.

    Submitted Sep 9, 2025

    Stayed Sep 6, 2025

    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!

  • Scott A.

    Submitted Aug 18, 2025

    Stayed Aug 15, 2025

    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.

  • Chris L.

    Submitted Aug 12, 2025

    Stayed Aug 6, 2025

    Great waterfront location, with nice beach and waterside screened porch-perfect for dinning.

  • Jonathan H.

    Submitted Jun 24, 2025

    Stayed Jun 16, 2025

    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!

  • Anthony L.

    Submitted May 18, 2025

    Stayed May 16, 2025

    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.

  • K- M.

    Submitted May 5, 2025

    Stayed Apr 28, 2025

    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!

  • Elizabeth K.

    Submitted Sep 28, 2024

    Stayed Sep 13, 2024

    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!

  • Submitted Sep 5, 2024

    Stayed Aug 30, 2024

    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.

  • Marianne B.

    Submitted Aug 27, 2024

    Stayed Aug 23, 2024

    I needed a quiet place to rest and Oh Happy Bay was pperfectpabsolutely perfect. I was so impressed

  • Juanita D.

    Submitted Aug 27, 2024

    Stayed Aug 18, 2024

    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!

  • SCOTT B.

    Submitted Aug 16, 2024

    Stayed Aug 8, 2024

    Really like this place

  • Courtney M.

    Submitted Aug 13, 2024

    Stayed Aug 3, 2024

    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.

  • Bryan B.

    Submitted Jul 6, 2024

    Stayed Jul 1, 2024

    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

  • Submitted Jul 2, 2024

    Stayed Dec 31, 1969

    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.

  • Thomas C.

    Submitted Jul 1, 2024

    Stayed Jun 21, 2024

    Had a great weekend. Place was perfect for us.

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Total

Includes taxes and fees
$1,077+
View details