Deep Hole stay.A stay at this Deep Hole vacation home places you within half a mile (1 km) of Oyster Bay and 3 miles (5 km) of Maui Jack's Waterpark. Chincoteague Channel and Captain Timothy Hill House are also within 3 miles (5 km).
Robert N. Reed Downtown Waterfront Park - 7 min drive - 2.6 miles
Chincoteague National Wildlife Refuge - 8 min drive - 3.0 miles
University of Maryland Eastern Shore - 59 min drive - 45.3 miles
Getting around
Ocean City, MD (OCE-Ocean City Municipal) - 72 min drive
Restaurants
Island Creamery - 4 min drive
McDonald's - 6 min drive
Ropewalk - 6 min drive
Teaguers - 4 min drive
Steamers - 4 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.
Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!
Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When was the last time you broke away from the day-to-day with those who matter most? Well, the time is now, and the Vacation Destination is Gray Pearl in the heart of Chincoteague Island. This beautiful Canal Front Home is located in prestigious Oyster Bay - serene and peaceful, yet close to everywhere you want to be. With 4 Bedrooms, 2.5 Baths, and a waterfront wonderland in your own backyard, there's no better place to make those amazing Vacation Memories.
Tucked away on a quiet Canal and surrounded by Whispering Pines, you won't even want to leave the grounds. You will love being able to fish and crab from your own backyard - oh, the wildlife you will see here. Watch Herons and Egrets fish for their morning meal as you relax on the Screened Porch. The wide Canal is perfect for bringing your Boat, Kayaks, or other Water Toys. Don't have kayaks? Just let us know and we are happy to help you with that! The calm waters of the Bay are perfect for kayaking, and just at the end of the Canal. There is so much fun to be had without even leaving your yard!
Gray Pearl is just as stunning on the inside. This huge 3,000 square foot home is light, bright, and spacious. You’ll love kicking back in the Living Area with Free WiFi, Flat Screen Smart TV, and comfy furnishings, after a fun-filled day at the Beach - which, by the way, is less than 10 minutes away! You can take in gorgeous Views - right from the Living Room sofa. The awesome layout of Gray Pearl is perfect for spending time together without ever feeling crowded. With warm wood accents and lots of wonderful natural light, it’s spacious and cozy, all at the same time.
The Chef in your family will love the enormous and well-stocked Kitchen, and the Breakfast Bar is perfect for a quick bite before hitting the Beach. Dining options you ask? Dine indoors in the spacious Dining Area, or Al Fresco on the Screened Waterfront Porch while taking in that salty, sweet air. Grab some Fresh Local Seafood from Gary Howard's, just around the corner, and fire up the Gas Grill. With any luck, you'll be steaming some Crabs you caught yourself in the Canal! You are also just a hop, skip, and jump away from some fabulous Chincoteague Restaurants, as well.
This wonderful home sleeps 10 in pure comfort in style with 3 Bedrooms on the 1st Floor, and a huge Bedroom Suite upstairs! Bedroom 1 is the Primary Bedroom and has a luxurious King Bed, and is dressed in beachy blues and whites. The Attached Full Bath has a Walk-in Shower. You also have access to the Waterfront Deck - just imagine slipping out to stargaze while the rest of your family is snoozing…..
Bedroom 2 is perfect for the kiddos or singles with 2 Twin Beds and lots of closet space. Right next door, Bedroom 3 has a comfy Queen Bed and is bright and beachy. There is a 2nd Full Bath with a Tub/Shower Combo convenient to the Bedrooms and Living Area.
Wandering upstairs, you’ll find Bedroom 4, which is a huge Bedroom Suite with a Living Area equipped with another Flat Screen TV and lots of comfy furniture. On one side, there is both a Full Bed and a Twin Bed, and on the other side, there is a Twin Daybed, so this room sleeps 4 comfortably, and would make a great area for the kids, or offer privacy for a couple! There is a Half Bath on this level, as well.
Gray Pearl truly is the perfect blend of fabulous Indoor and Outdoor Living. Spend the days exploring Assateague National Seashore, just a 5 minute drive away, and visit our Famous Wild Ponies, collect shells, swim in our pristine waters, or just lounge in the sunshine. Whatever your pleasure, you’re sure to find it at Gray Pearl on Chincoteague Island!
Gray Pearl - Time wasted at the Beach is well spent.....
Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
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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)
Fire extinguisher
General
Garden
Policies
Check-in
Contactless check-in available
Check-out
Contactless check-out available
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
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
Safety features at this property include a fire extinguisher
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
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. 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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.
Property is also known as
165229
Frequently asked questions
How close is Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! to the airport?
This vacation home is 56.6 mi (72-min drive) away from the Ocean City, MD (OCE-Ocean City Municipal) airport, the closest popular airport to the property.
Does Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! to the beach?
This vacation home is 7 mi (25-min drive) from Bow Beach.
Does Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!?
No, there is no casino at this vacation home.
Is there free parking at Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!?
Free parking is not available at this vacation home.
Does Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! have a pool?
This vacation home does not have a pool.
Does Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! have a spa?
There are no spa services available at this vacation home.
How close is Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! to downtown Chincoteague?
This vacation home is 1.7 mi away from Chincoteague.
Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 3 out of 3 reviews
10 - Excellent
3
Rating 8 - Good. 0 out of 3 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 3 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 3 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 3 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Jody B.
Nov 5, 2025
Liked: Cleanliness
We had a wonderful stay at the 'Gray Pearl'. The home was beautiful and fit our needs perfectly. Very clean and comfortable.
Jody B.
Stayed 2 nights in Oct 2025
10/10 Excellent
Sarunas J.
Jun 7, 2025
Liked: Cleanliness
Clean and well maintained property. Easy check-in, good location, plenty of space and amenities. Area seemed very safe. Nice balcony/porch to sit outside. Excellent communication from the management.Still everything deserves a clear 5-stars, but please upgrade the kitchen garbage can, since it is not a user-friendly piece of equipment.
Sarunas J.
Stayed 3 nights in Jun 2025
10/10 Excellent
Richard F.
May 11, 2025
Liked: Cleanliness
Great house
The house was beautiful and big enough for 6 adults and 4 kids with plenty of space right on the canal. The neighborhood was peaceful and quiet, would definitely stay there again.