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Beachfront Home Minutes to Downtown Annapolis Dogs OK | Cottage in Annapolis

9.8 (36 Reviews) |   Pet Friendly   3 Bedrooms  2 Bathrooms  8 Guests
Annapolis Cottage | Beachfront Home Minutes to Downtown Annapolis Dogs OK

3 Bedroom Cottage in 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.

Beachfront Home Minutes to Downtown Annapolis Dogs OK is located in Annapolis. Beachfront Home Minutes to Downtown Annapolis Dogs OK provides accommodation, featuring Air Conditioner, TV, View, among other amenities. This Cottage features Air Conditioner, TV, View, to make your stay a comfortable one.

Beachfront Home Minutes to Downtown Annapolis Dogs OK has 3 Bedrooms , 2 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the Annapolis has interesting places to visit. If you want to learn more about the Cottage in Annapolis, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 11:00 am
Child Policy Children are welcome.
Pet Policy Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy Smoking is not permitted
Other Policy 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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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
 
Annapolis, 21403, USA

What Our Guests say 500 + Reviews

May 19, 2025 05:12:02 AM
Summary: We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting.
Anthony L. Anthony L.
May 6, 2025 12:53:43 AM
Summary: Everyone in the family who stayed here loved it -- all ages! The open floor plan made spending time together inside easy and there was also enough space when we were sitting outside watching the sailboats and listening to the water hit the sandy beach. The house is well equipped (dishes, glasses, silverware, living room seating, big dining room table, sheets and towels) and we found it much cleaner than other homes we've stayed. And it's dog friendly! The house is on a quiet street almost at the end of the road, so peaceful. We truly enjoyed the week we spent here!
K- M. K- M.
Sep 29, 2024 01:37:54 AM
Summary: 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!
Elizabeth K. Elizabeth K.
Sep 6, 2024 06:38:38 AM
Summary: 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.
Aug 28, 2024 05:23:23 AM
Summary: I needed a quiet place to rest and Oh Happy Bay was pperfectpabsolutely perfect. I was so impressed
Marianne B. Marianne B.
Aug 28, 2024 05:03:17 AM
Summary: 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!
Juanita D. Juanita D.
Aug 17, 2024 06:38:15 AM
Summary: Really like this place
SCOTT B. SCOTT B.
Aug 13, 2024 08:13:20 AM
Summary: 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.
Courtney M. Courtney M.
Jul 6, 2024 07:25:31 AM
Summary: 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
Bryan B. Bryan B.
Jul 3, 2024 06:39:03 AM
Summary: 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.
Brooke B. Brooke B.

FAQ's

Is this Annapolis cottage pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Annapolis cottage have a swimming pool?

No, this Annapolis cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Annapolis cottage?

Best-rates for the Annapolis cottage starts from $933 per night with includes Parking, Ocean View, Sports/Activities, Air Conditioner, TV, View, Wellness Facilities, Fireplace/Heating, Barbecue/Outdoor Cooking, Internet, Pet Friendly, Balcony/Terrace, Security/Safety, Bedding/Linens, Guest Services, Child Friendly, Kitchen, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Annapolis cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Annapolis cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Annapolis cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Annapolis cottage?

Based on the information reported by the owner or manager, the Annapolis cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Annapolis cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the Annapolis cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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