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Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property

Photo gallery for Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Interior
Fridge, microwave, oven, stovetop
Dining
Exterior
Interior

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms

Popular amenities

  • Dryer
  • Fireplace
  • Parking available
  • Washer
  • Kitchen
  • Pet friendly

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 Oasis with Private Dock, Firepit & Kayaks

Available for Commissioning Week 2025!

Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Welcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts.

Outdoor Features:
Private dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included)
Expansive lawn perfect for cornhole, yard games, or simply soaking up the view
Firepit for cozy evenings with s'mores and stories
Hammock for relaxing with a good book or simply enjoying nature
Parking for 3-4 cars on the driveway

Indoor Highlights:
Bright, airy sunroom with harbor views for board games and family time
Sleek, modern kitchen with large picture windows framing the waterfront
Living room featuring a smart TV and gas fireplace for cozy evenings
Small desk and WiFi printer for remote work convenience

Neighborhood amenities:
Swimming beach
Exercise: Beach volley ball court, 1-mile exercise circuit course, 12' climbing wall, 16' rope climb,
Fishing pier and boat ramp
Playgrounds, nature preserve, picnic areas, beach gazebos

Starter Amenity Pack:
We've got you covered with essentials to make your stay stress-free, including:
Coffee, sweeteners, dish soap, and paper towels
Soap, shampoo, conditioner, and hand sanitizer
Freshly-laundered sheets and towels for every guest

Sleeping Arrangements (3 BR / 2 BA, Sleeps 8):
Front Queen Bedroom: Queen bed, shared full bath in the hall
Waterfront Bedroom: Full bed, shared full bath in the hall
Bunk Bedroom: Twin bunk beds (two twins), shared hall bath
Loft: Full bed above the living room

House Rules:
Family rentals only; one guest must be at least 25 years of age
Dog-friendly (please clean up after your pet) with $150 fee paid prior to check-in
No smoking, parties, or events
Quiet hours from 9:00 pm to 8:00 am
Check-in: 4:00 pm | Check-out: 11:00 am

Property Distance to:
-Downtown Annapolis – 4 miles (10 mins)
-U.S. Naval Academy – 4.5 miles (12 mins)
-Washington, DC – 35 miles
-Baltimore - 20 miles

Create lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape!

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Add dates for prices

Property amenities

Beach

  • Beach nearby
  • Beach loungers

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • No elevator
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Bicycle parking
  • Bicycle storage
  • Kayak
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • At least 80% lighting from LEDs
  • Bicycle parking
  • Bicycle storage
  • Energy-saving switches in guestrooms
  • Garden
  • Recycling

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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 allowed
Service animals are welcome, and 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 indicated there is a carbon monoxide detector on the property
Host has indicated 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

We should mention

This property does not have elevators

Property is also known as

14332

About the neighborhood

Map
MD, Annapolis

What's nearby

  • Maryland Quiet Waters Park - 4 min drive - 3.2 km
  • Annapolis City Dock - 9 min drive - 7.5 km
  • Annapolis Maritime Museum - 9 min drive - 6.9 km
  • U.S. Naval Academy - 10 min drive - 7.2 km
  • Navy-Marine Corps Memorial Stadium - 11 min drive - 9.9 km

Getting around

  • Odenton Station - 26 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Little Italy Annapolis - ‬7 min drive
  • ‪Boatyard Bar & Grill - ‬9 min drive
  • ‪Carrol's Creek Cafe - ‬9 min drive
  • ‪Annapolis Yacht Club - ‬9 min drive

Frequently asked questions

Is Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks?

Check-out is at 11:00 AM.

Where is Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks located?

Located in Oyster Harbor, this vacation home is within 3 mi (5 km) of Maryland Quiet Waters Park, Bay Bridge Market Place Shopping Center, and Historic Mount Moriah AME Church. Historical Society of Talbot County and Annapolis Golf Club are also within 3 mi (5 km).

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Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks Reviews

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

10/10 Excellent

Calin L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location on the water with a dock!

We had a great Springtime vacation with kids and a grandparent - our kids enjoyed kayaking and paddle boarding from the doc and gramps was very comfortable watching from the yard. It’s a very convenient location for a family. House was small but had everything we needed and well maintained. We recommend it!!
Stayed 3 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sarah M.

Amazing choice for young child!

We have a four year old and this was an absolutely perfect place for a get away. We launched kayaks from the dock and the water is calm and easy to navigate. The lawn is great for running and playing. And the beach is so close and set up for little ones. The neighborhood is very family oriented and there were a bunch of kids swimming and plying on the playground. The house has everything you need and the room in back with each is perfect for eating and lounging.

10/10 Excellent

Jenn G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice location in quiet neighborhood

We enjoyed our stay. The house is laid out a bit quirky, but there was room for everyone and it had everything we needed. The kids really enjoyed the fire pit and I wish it would’ve been warmer so we could have used the kayaks.We were able to access downtown Annapolis very easily for a walking tour and a visit to the Naval Academy. The drawers in the kitchen are a bit odd, however we found everything eventually.Overall, great stay and no complaints.
Stayed 3 nights in Mar 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Mary C.

A Perfect Stay at The Pearl!

We had an incredible experience at The Pearl and can’t say enough good things about both the home and the iTrip team. After a last-minute disaster with an Airbnb rental in Epping Forest, we were scrambling for a place to stay over my son’s graduation weekend. We had a packed schedule, including hosting his prom send-off, and needed a comfortable, reliable home fast. The iTrip team was absolutely amazing—responsive, kind, and efficient. They got the house prepped and ready for us in under 24 hours! As for The Pearl—we LOVED it. The layout was thoughtful and spacious, with plenty of room for our family to relax and celebrate. The bedrooms were cozy and the beds incredibly comfortable. The kitchen was well-stocked, and we especially appreciated the quality beach towels and other thoughtful touches throughout the home. The views were lovely, and while we didn’t get to take full advantage of the beach privileges that come with the rental, it was great to know they were available. The backyard was a dream—tons of space, a great firepit, a peaceful pier, plus bikes, kayaks, and more. You can tell the owners and iTrip team really care about making the stay special. After such a rocky start to our weekend, The Pearl ended up being the perfect home base for a very special occasion. We’ll definitely be back, and I’m already recommending it to friends and family. A true hidden gem!