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Waterfront dog-friendly home with beach just mins to Downtown Annapolis

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Welcome to the renovated kitchen at Oh Happy Bay!
A rare find! Private beach access to safe swimmable, boatable, safe water on the Bay!
Spacious dining room located between the kitchen and family room
The upstairs sitting room is spacious enough for an air mattress (provided).
Views of the back deck, balcony and hammock.

Reviews

9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Beach view
  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen
  • Parking available

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    ‪10 min drive‬
  • Navy-Marine Corps Memorial Stadium
    ‪11 min drive‬
  • U.S. Naval Academy
    ‪16 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪22 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
Porch or lanai
Outdoor shower
Kitchen
Balcony
Garden

About this property

Waterfront dog-friendly home with beach just mins to Downtown 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.

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

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 Alumni Hall or Navy-Marine Corps Memorial Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • Annapolis City Dock - 10 min drive - 6.7 km
  • Annapolis Maritime Museum - 10 min drive - 6.4 km
  • Maryland State House - 11 min drive - 7.2 km
  • Navy-Marine Corps Memorial Stadium - 11 min drive - 8.3 km
  • U.S. Naval Academy - 16 min drive - 9.9 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪The Choptank - ‬10 min drive
  • ‪O'Brien's Annapolis' Original Steakhouse - ‬10 min drive
  • ‪Boatyard Bar & Grill - ‬9 min drive
  • ‪Pusser's Caribbean Grille - ‬10 min drive
  • ‪Carrol's Creek Cafe - ‬10 min drive

Frequently asked questions

Is Waterfront dog-friendly home with beach just mins to Downtown Annapolis pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Waterfront dog-friendly home with beach just mins to Downtown Annapolis?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront dog-friendly home with beach just mins to Downtown Annapolis?

Checkout is at 11:00 AM.

Where is Waterfront dog-friendly home with beach just mins to Downtown Annapolis 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 29 reviews
Rating 8 - Good. 1 out of 29 reviews
Rating 6 - Okay. 1 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Elizabeth K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely lovely Beachside getaway

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!
Stayed 6 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

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

10/10 Excellent

Marianne B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Heavenly Haven

I needed a quiet place to rest and Oh Happy Bay was pperfectpabsolutely perfect. I was so impressed
Stayed 3 nights in Aug 2024

10/10 Excellent

Juanita D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A great stay at Oh Happy Bay!

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!
Stayed 4 nights in Aug 2024

10/10 Excellent

SCOTT B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

Really like this place
Stayed 4 nights in Aug 2024

10/10 Excellent

Courtney M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location

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.
Stayed 5 nights in Aug 2024

10/10 Excellent

Bryan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

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
Stayed 4 nights in Jul 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

Brooke B.

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.

10/10 Excellent

Thomas C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sailing Weekend.

Had a great weekend. Place was perfect for us.
Stayed 4 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

D S.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

james T.

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.
Stayed 4 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

D W.

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.

10/10 Excellent

Monica M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cousins Trip to Chesapeake Bay

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!
Stayed 2 nights in Mar 2024

6/10 Okay

MAGGIE B.

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.
Stayed 5 nights in Mar 2024

10/10 Excellent

Penny B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Rest & relaxation getaway

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.
Stayed 3 nights in Feb 2024

10/10 Excellent

Julie N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely beautiful

Very family friendly with a cute little beach. Perfect get away place with lots of character.
Stayed 4 nights in Dec 2023

10/10 Excellent

Denise W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Christmas trip

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.
Stayed 4 nights in Dec 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Joseph F.

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!
Stayed 3 nights in Dec 2023

10/10 Excellent

David C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The View

The location is great. I would bring pots and pans. We went and bought some.
Stayed 5 nights in Nov 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Trish O.

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!

10/10 Excellent

Lisa R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Great location! Beautiful home!
Stayed 2 nights in Oct 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Hilary

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!

10/10 Excellent

Richard T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Yes Happy Bay

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.
Stayed 3 nights in Sep 2023

10/10 Excellent

Leslie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Week in Annapolis

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!
Stayed 5 nights in Jul 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

kim m.

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!
Stayed 6 nights in Jun 2023

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests