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

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December 2024
January 2025

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

On the beach, sun loungers, beach towels
Fridge, microwave, oven, stovetop
Point of interest
Exterior
3 bedrooms, desk, iron/ironing board, free WiFi

Reviews

9.8 out of 10

Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Beach view
  • Parking available
  • Washer
  • Gym
  • Pet-friendly
  • Kitchen

Explore the area

Map
Annapolis, MD
  • Annapolis Landing Marina
    8 min walk
  • Maryland Quiet Waters Park
    7 min drive
  • Annapolis Maritime Museum
    10 min drive
  • Annapolis, MD (ANP-Lee)
    19 min drive

Room options

Similar properties

About the area

Annapolis

On the beach.At this cottage, you'll be steps from Annapolis Sailing School and within a 10-minute walk of Annapolis Landing Marina. Sparrows Beach and Bay Bridge Market Place Shopping Center are also within 3 miles (5 km).

What's nearby

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

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Visit the magic of Annapolis during the Holiday Season
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

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
-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.

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Property amenities

Beach

  • On the beach
  • Beach towels
  • Beach sun loungers

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Coffee/tea maker
  • Electric kettle
  • Paper towels
  • Blender

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 2 bathrooms
  • Bathtub or shower
  • Shampoo
  • Outdoor shower
  • Towels provided
  • Hair dryer
  • Soap
  • Toilet paper

Living spaces

  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Washing machine and dryer
  • Near laundromat

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 a health or beauty spa
  • Near a hospital
  • Near the bay

Things to do

  • Fitness center
  • Water sports equipment
  • Fitness facilities nearby
  • Boat on site
  • Hiking nearby
  • Cycling nearby
  • Jet skiing nearby
  • Birdwatching nearby
  • Golf nearby
  • Fishing nearby
  • Kayaking nearby
  • Power boating nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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
Onsite 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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited.

Property is also known as

12207

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

Reviews

9.8

Exceptional

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

Reviews

10/10 Excellent

Elizabeth K.

Liked: Cleanliness
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

10/10 Excellent

Marianne B.

Liked: Cleanliness
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
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
Great place
Really like this place
Stayed 4 nights in Aug 2024

10/10 Excellent

Courtney M.

Liked: Cleanliness
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
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

10/10 Excellent

Thomas C., Pittsford

Liked: Cleanliness
Sailing Weekend.
Had a great weekend. Place was perfect for us.
Stayed 4 nights in Jun 2024

10/10 Excellent

Monica M.

Liked: Cleanliness
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
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
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
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
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

10/10 Excellent

David C.

Liked: Cleanliness
The View
The location is great. I would bring pots and pans. We went and bought some.
Stayed 5 nights in Nov 2023

10/10 Excellent

Lisa R.

Liked: Cleanliness
Wonderful stay!
Great location! Beautiful home!
Stayed 2 nights in Oct 2023

10/10 Excellent

Richard T.

Liked: Cleanliness
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
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

10/10 Excellent

Therese G.

Liked: Cleanliness
Perfect
Oh Happy Bay was certainly that. A charming cottage, well equipped, right on the bay with lovely views of sail boats passing by. Ample parking, comfy beds, beautiful sunrises and sunsets. Perfect!
Stayed 14 nights in Apr 2023

10/10 Excellent

Audrey H.

Liked: Cleanliness
This was the perfect meetup for myself, my daughter and two granddaughters.
We really enjoyed the property with all its appeal, the beach, sunrise, comfort, quiet. It is in close driving proximity to downtown Annapolis where we spent the day enjoying a boat tour and shopping. Everything was up to par in the listing if not better.
Stayed 3 nights in Apr 2023

10/10 Excellent

Amy P.

Liked: Cleanliness
Perfect Vacation Spot on the Bay
"Oh Happy Bay" could not have been a more perfect spot for our weekend trip to Annapolis. There was plenty of room for all 4 of the adults visiting. The pictures can't do justice to how special this location is. The water is right out the backdoor and the yard is appointed in a way to allow multiple spots to sit and relax. The home was absolutely beautiful. There is tons of natural light and the furnishings in every room make it comfortable. Literally at every turn there was a special extra touch. Thank you to Sean for a top tier stay. Accommodations and extra touches were so appreciated and the check-in and check-out was seamless and easy. Thank you also to Cathy for timely communications and answering any questions we had. We could not have been happier with our stay - it was the perfect way to celebrate my Dad's birthday. The entire family plans to stay here again! Highly recommend!
Stayed 3 nights in Apr 2023

10/10 Excellent

robin h.

Liked: Cleanliness
Great stay
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!!
Stayed 3 nights in Mar 2023