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Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake

Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake

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Welcome to the renovated kitchen at Oh Happy Bay!
The kitchen opens up to the family room and dining room.
The waterfront room upstairs has a King bed, small balcony and sitting room.
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

Overview of Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake

Reviews
9.8 out of 10 Exceptional
3 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
  • Free WiFi
  • Air conditioning

Explore the area

Map
Annapolis, MD
  • Popular LocationAnnapolis City Dock10 min drive
  • Popular LocationAnnapolis Maritime Museum10 min drive
  • Popular LocationU.S. Naval Academy16 min drive
  • AirportAnnapolis, MD (ANP-Lee)18 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
Kitchen
Balcony
Garden

About this property

Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake

*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

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
Premier Host
Premier Host

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

House Rules

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

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
  • William Paca House - 10 min drive
  • Annapolis Maritime Museum - 10 min drive
  • Maryland State House - 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
  • Latitude 38 - 10 min drive
  • Annapolis Yacht Club - 9 min drive
  • Pusser's Caribbean Grille - 10 min drive

Frequently asked questions

Is Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake?

Check-in begins at 4:00 PM.

What time is check-out at Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake?

Checkout is at 11:00 AM.

Where is Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake 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.
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Rating 10 - Excellent. 18 out of 19 reviews" "
Rating 8 - Good. 0 out of 19 reviews" "
Rating 6 - Okay. 1 out of 19 reviews" "
Rating 4 - Poor. 0 out of 19 reviews" "
Rating 2 - Terrible. 0 out of 19 reviews" "

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

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

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Premier Host

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