Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

9.6 / 10.0

Outstanding(19 Ratings)

House in Anne Arundel County, MD

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Top-tier experienceOne of the higher cost properties in the area

About this house rental

The Pearl of Oyster Harbor

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Whether it's relaxation or activity you seek, you'll find it all in the gorgeous waterfront setting of The Pearl of Oyster Harbor. This is a stunning place for boating and swimming from the private dock, playing yard games at the water's edge, and gathering around the firepit for s'mores and stories once the sun goes down.

This peaceful, two-story home boasts an expansive piece of property in Oyster Harbor, a private community on the Annapolis Neck Peninsula along an inlet of the Chesapeake Bay. The flat, beautiful lawn stretches all the way to the dock, where you're welcome to tie up your boat, launch one of the kayaks (two adult, one youth), or take out the inflatable paddleboard. (The bay can be shallow and tricky in parts; please familiarize yourself with the water before you navigate a boat.)

When you're not strolling less than half a mile to Oyster Harbor Private Beach, make a day of it in the backyard by playing cornhole, yard toss, or Slip-N-Slide. Light the gas grill for a lunchtime barbecue, dine in the coastal breeze on the deck or at the picnic table, and linger all afternoon in the hammock while watching passing boats, birds, and marine life.

Built in 1960 and thoughtfully renovated in the years since, this unique cottage maintains much of its original character while offering modern touches at every turn. Large picture windows and rear glass doors frame the harbor - a lovely view you can take in as you cook in the sleek kitchen, make plans over breakfast each morning, and play board games and cards in the sunroom. In the evenings, enjoy an inviting living room with a smart TV and gas fireplace, three cozy bedrooms, and a sleeping loft. The small desk in the bunk room has a WiFi printer, making it perfect for remote work.

Things to Know
Check-in time: 4:00 p.m.
Check-out time: 10:00 a.m.
All guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.
No smoking is permitted anywhere on the premises.
This home is dog-friendly, but only 2 dogs are allowed per reservation. Neighbors are uber-sensitive to barking and off-leash dogs, so please be pet-friendly to neighbors.
Keep your dogs on a leash when outdoors. Please do not leave dogs in the yard unattended. Dogs must also be crated in the street-facing bedroom if you leave them alone in the house.

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us. The pet fee is per stay and ranges between $150 and $200, depending on the bedroom count, and will apply for each additional dog.

Parking notes: There is free parking available for 4 vehicles.

Security camera details: Front door and towards dock

Dock details: A private dock in which guests will be able to tie their boats up to. However, please keep in mind that the water can be shallow and tricky, please be aware when boating or swimming.

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Balcony or Patio

Dishwasher

Garden

Family friendly

Map of Anne Arundel County, MD

Nearby attractions

Smithsonian National Museum of Natural History

48.3 mi

National Museum of African American History and Culture

48.8 mi

RRRR

Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

RRRR

9.6 / 10.0

Outstanding(19 Ratings)

House in Anne Arundel County, MD

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Top-tier experienceOne of the higher cost properties in the area

About this house rental

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Balcony or Patio

Dishwasher

Garden

Family friendly

Map of Anne Arundel County, MD

Nearby attractions

Smithsonian National Museum of Natural History

48.3 mi

National Museum of African American History and Culture

48.8 mi

Ratings and reviews

9.6 / 10.0

Outstanding(19 Ratings)

8.0 / 10.0

Sep 2024

This was a wonderful spot for a get-a-way. The house was nice, property large, dock wonderful, and location perfect! I would definitely stay again.

8.0 / 10.0

Aug 2024

Very comfortable stay for group of 5. Lots to do on the property with wide array of sports equipment, games, fully stocked kitchen and variety of sleeping arrangements in 4 bedrooms.

10.0 / 10.0

Aug 2024

This house surpassed our expectations. Above all, the backyard that opens onto the water was a little peace oasis, ideal for morning coffee on the deck, evening meals, stargazing and kayaking. The fact that it was enclosed was perfect to let our lab wander around and even take a dip in the creek. The house itself is quiet, pretty but unpretentious, and the common spaces are really pleasant. The kitchen is very well equipped, and though the beds are on the small side, we all felt rested. Also, perfect location close to Annapolis sailing school, Quiet Water Park for the dog, and 15mn from downtown Annapolis. Top experience, great value for money, easy check in and out, and responsive management. Highly recommend it.

8.0 / 10.0

Aug 2024

Plenty of outdoor activities as well as indoor board games. Beautiful dock and view. Nice, quiet, friendly neighborhood. You can definitely tell this is a pet friendly home. We had to contact Vacasa a few times and I was not pleased with how they handled our requests.

10.0 / 10.0

Jun 2024

Location Perfect for our small group to relax

10.0 / 10.0

May 2024

We gathered her for Mother’s day, family from OH and DE. Great location if u’d like to go sightseeing in Annapolis or DC. Also great to just chill at the house. We loved the outdoor amenities; the yard, deck and pier. Great place to play and gather and relax. The house was decorated so cute and had enough towels for everyone as well as dishes, cookware, space and games. The house also had plenty of towel hooks, hampers, and luggage racks in the bedrooms, something that many property owners don’t think about. Also loved the use of the toiletries available in each bathroom. Just bring ur clothes and enjoy the rest.

10.0 / 10.0

Apr 2024

This is the place to stay if you're looking to get away. Great views and sunrises. They have kayaks, fishing poles, bicycles, out door games, fire pit, grill, and a large patio. Inside there's board games and a large Florida room in case it rains and you can't enjoy the outdoor activities. Our family had a great time hanging out, making smores, and enjoying each others company while we got to spend time together here. Everyone should stay here at least once.

10.0 / 10.0

Apr 2024

We spent our spring break here with 4 of our children. We are a blended family so this location turned out to be the perfect location for us to see family and explore a new place. This house was just perfect for us and we will have so many great memories from our visit. The house smelled amazing, was clean and organized. We loved all of the art work, books, and games that were available. The outdoor accommodations were helpful. We played games, kayaked, had a cookout and made smores over the fire pit. My fiancé proposed to me on the dock on the night of the full moon so that I will never forget. It was picture perfect! We enjoyed some of the local spots and sightseeing. We really loved the indoor fire place as well. The management company and owners were very helpful and responsive if we had any questions during our stay. Hope to make it back one day! Thank you so much.

10.0 / 10.0

Mar 2024

The space was a well laid out small space with lots of ingenious touches. It had many charming beach/nautical nods, and functionality in decor. The kitchen had everything needed for basic meal preparation, and a few extras such as materials for a crab bake. The view from the sunroom was amazing, and the views only got better as you went out to the porch, yard, and onto the dock. We saw so many different varieties of birds in the backyard and on the water. Binoculars and a telescope helped with viewing. The neighborhood was quiet and lots of people were walking their dogs. A private neighborhood beach access about a half mile down the road was another lovely feature.

8.0 / 10.0

Jan 2024

Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!

10.0 / 10.0

Nov 2023

Magnificent water views

8.0 / 10.0

Nov 2023

Everything was great. The only thing missing was access to laundry.

10.0 / 10.0

Nov 2023

Overall excellent home, very comfortable and a great view on the bay. Morning sunrise is the best!

10.0 / 10.0

Oct 2023

Quiet neighborhood, breathtaking views from house looking to water. All beds noted to be very comfortable!

8.0 / 10.0

Oct 2023

Great location and really nice place. The only problem that I had was that there weren’t any toiletries or standard amenities. No toilet paper, or soap.

10.0 / 10.0

Sep 2023

We loved watching the birds on the dock and being on the water.

10.0 / 10.0

Sep 2023

We had a wonderful, restful stay at The Pearl. The house is comfortable, the yard is great for dogs, and the views are beautiful and relaxing. Some additional amenities include spices and condiments, lots of utensils, and nice parks nearby.

FAQs

How much does this house cost compared to others in Anne Arundel County?

The average price for a rental in Anne Arundel County is R 3,826 per night. This rental is R 5,646 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard?

We found 11 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.

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Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

House in Anne Arundel County, MD

Reasons to book

About this house rental

Amenities

Map of Anne Arundel County, MD

Nearby attractions

Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard

House in Anne Arundel County, MD

Reasons to book

About this house rental

Amenities

Map of Anne Arundel County, MD

Nearby attractions

Ratings and reviews

FAQs

How much does this house cost compared to others in Anne Arundel County?

Is parking included with this house?

Is there a pool at this house?

Is Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard pet friendly?

What amenities are available at Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard?

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