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Waterfront home with beach on the Chesapeake Dog-Friendly

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Property grounds
Property grounds
Exterior
Desk, iron/ironing board, free WiFi, bed sheets
Dining
Reviews
9.8

Exceptional

Popular amenities

  • Beach viewBeach viewBeach view
  • DryerDryerDryer
  • GymGymGym
  • WasherWasherWasher
  • Barbecue grillBarbecue grillBarbecue grill
  • KitchenKitchenKitchen

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

Room options

Similar properties

About the neighborhood

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
  • Latitude 38 - 10 min drive
  • Annapolis Yacht Club - 9 min drive
  • Pusser's Caribbean Grille - 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 home with beach on the Chesapeake Dog-Friendly

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

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundromat nearby
  • Washing machine

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/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina

Things to do

  • Boat on site
  • Gym on site
  • Water sports equipment on site
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks 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)

General

  • Garden

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

Frequently asked questions

How close is Waterfront home with beach on the Chesapeake Dog-Friendly to the airport?

This cottage is 22.9 mi (31-min drive) away from the Fort Meade, MD (FME-Tipton) airport, the closest popular airport to the property.

Does Waterfront home with beach on the Chesapeake Dog-Friendly have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is Waterfront home with beach on the Chesapeake Dog-Friendly to the beach?

This cottage is on the beach. Don't forget your sunscreen!

Does Waterfront home with beach on the Chesapeake Dog-Friendly offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at Waterfront home with beach on the Chesapeake Dog-Friendly?

No, there is no casino at this cottage.

What time is check-in at Waterfront home with beach on the Chesapeake Dog-Friendly?

Check-in begins at 4:00 PM.

Is there free parking at Waterfront home with beach on the Chesapeake Dog-Friendly?

Free parking is not available at this cottage.

Does Waterfront home with beach on the Chesapeake Dog-Friendly have a pool?

This cottage does not have a pool.

Does Waterfront home with beach on the Chesapeake Dog-Friendly have a spa?

There are no spa services available at this cottage.

How close is Waterfront home with beach on the Chesapeake Dog-Friendly to downtown Annapolis?

This cottage is 1.3 mi away from Annapolis.

Waterfront home with beach on the Chesapeake Dog-Friendly Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 19 out of 20 reviews" "
Rating 8 - Good. 0 out of 20 reviews" "
Rating 6 - Okay. 1 out of 20 reviews" "
Rating 4 - Poor. 0 out of 20 reviews" "
Rating 2 - Terrible. 0 out of 20 reviews" "

9.8/10

Cleanliness

Reviews

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