Oh Happy Bay

3 BR
2 Baths
Sleeps 8


*Still available for 2024 Commissioning Week - 5-night minimum!

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


-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

-No smoking

-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.

7027 Bay Front Dr Annapolis, MD 21403

Sleeping Arrangements

Waterfront King King
Upstairs Queen Full
Main floor Queen
Family Room Sofa Full

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed


Air Conditioning
BBQ Grill
Bath Towels
Bay View
Beach Front
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Covered Patio
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Outdoor shower
Parking Available
Pets Considered
Private Backyard
Private entrance
Screened Patio
Self Check-In
Smoke Detector
Smoke alarms
Washing Machine
Water View
body wash
hot water



Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit Oh Happy Bay. Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund.


Balance is due 30 days prior to arrival date and includes a refundable damage deposit. The balance is due on _BalanceDueDate_. Payment may be made by major credit card. 


Cancellations must occur at least 30 days prior to arrival date, or WILL BE CHARGED THE FULL AMOUNT. If cancellation occurs 30 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee.


No BBQ grills of any kind are permitted in the unit. No open flames permitted in the unit.


If you wish to bring your dog, you will need to pay the $150 non-refundable pet deposit per pet prior to arrival.  If you bring an unathorized pet on to the property, you will be asked to vacate immediately with no refund of rent or damage deposit. Homeowner and Agent assume no responsibility for any illness or injury that may occur to pets or humans while on the premises. Homeowner and Agent assume no responsibility for the behavior of the pet(s); that responsibility is the Tenant owner.


Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.


There is no daily maid service. Linens and towels are included and not to be taken from the unit. There is a $_CleaningFee_ one time cleaning fee.


No compensation will be given for temporary outage of electricity, gas, water or cable. 


Your damage deposit will be forfeited and you will incur an additional charge for cleaning and deodorizing if any evidence of smoking is found.


Owner or owner's agents may enter the premises: in case of an emergency; to make any necessary or agreed upon repairs, alterations, or improvements; supply necessary or agreed upon services or show the premises to prospective purchasers, renters or contractors.  24 hours notice of Owners intent to enter will be given (except in the case of an emergency).


  1. Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. Please leave all used towels on the floors of the bathrooms and beds linens should all be left on each bed for housekeeping.
  2. All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. If these items are not completed, the guest will be charged an additional cleaning fee. 
  3. The maximum number of occupants shall not exceed 8 people, not including a child in a crib.
  4. Furnishings are not to be removed from the premises for use outside or in other properties.
  5. No Smoking.
  6. Reservations are not made by or for a minor, defined as any person under the age of 25.
  7. Tenant and any guest of Tenant shall obey all laws of the state of Maryland, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of Maryland or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.
  8. All noise must be brought inside by 10pm. Failure to do so could result in a $500 fine.


Tenant and all other occupants will be required to vacate the premises and forfeit the rental fee and security deposit for: Occupancy exceeding the sleeping capacity of 8 people, using the premises for illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.


iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.


Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.


Needed Time Away
5/5 stars
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
Great House
5/5 stars
Our arrival was seamless and entry was easy, The house is terrific and the location is amazing! We are truly enjoying our time here!
5/5 stars
Wonderful home! Perfect getaway! We loved every aspect of this home! Quaint, clean, spacious, and gorgeous views! Would highly recommend and for sure home to use again when coming back to visit our daughter at USNA
- Lisa
Hidden gem right by Annapolis!
5/5 stars
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
Yes, Happy Bay
5/5 stars
We stayed at Oh Happy Bay with our son, his wife and their two toddlers. The house was very nice, with plenty of space. The kitchen was well stocked with cookware and appliances. The star of the show was the private sandy bay beach just steps from the back door. The kids loved it. The waves were minimal, and there was plenty of space for the adults to swim. The dog enjoyed chasing balls around the back yard and into the water. The neighborhood was quiet but only a few minutes from Eastport’s restaurants and from downtown Annapolis. We loved it. Five stars for sure.
- Richard
Great stay by the bay!
5/5 stars
Everything was perfect. You couldn’t Sk for a better home and location. The deer who visited us daily was an added touch!
- Kim
Great stay!
5/5 stars
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!!
- Mid mom and dad

Book Your Stay

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Contact Manager

Phone (410) 571-4076