We offer services for vacation rental owners who need assistance managing the details of their rental business. From websites, marketing, housekeeping, and emergency services - we can help you rent with confidence and peace of mind. As a property owner, or potential property owner, you’ve obviously fallen in love with the beach, just as we have. Seaside Vacations was founded with the belief that there was a better way to provide outstanding service, implement market leading technology, and provide the very best Eastern Shore Vacation experience possible all while providing value to both our Partners and Guests.

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 ...