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.

Sky above, Sand below, Peace within….. Here at Seaside, we believe that finding the “perfect” Vacation Home is so much more than merely finding a place to lay your head at night. We are all about “Experiences” ~ and a stay at ‘East Side Breezes’ is just that ~ a blissful Experience that will be treasured by your family for years to come. This spectacular Family Home sits on the ever-popular East Side of our beautiful Little Island by the Sea, and faces the Assateague Channel and Assateague Light - and y’all, those Views! East Side Breezes is unique in so many wonderful ways - you’ll feel this as soon as you pull into the driveway! As you climb the few stairs leading to the Waterfront Deck, that salty, sweet sea breeze hits your face, welcoming you to paradise. You can already see yourself never wanting to leave the comfy Adirondack Chairs that face the Channel. Upon entering, East Side Breezes welcomes you like an old friend. With Warm Wood Trim and Light Pine-like Flooring, it instantly feels like home. This quintessential Chincoteague Cottage has received many updates over the years, including the addition of a 2nd Level. This gives it everything you love about yesteryear, plus the Modern Amenities you want and need. You’ll love kicking back in the spacious Living Area with Brand New Furnishings, including a Queen Sleeper Sofa, after a fun-filled day exploring Assateague National Seashore, and enjoying Flat Screen Streaming TV and Free WiFi. We just love the fact that ESB has TWO Living Areas - upstairs and downstairs. Just off the Living Area, you’ll find the Kitchen and huge Dining Room with plenty of room for all to gather for meals. The Chef in your family will appreciate the Well-Stocked Kitchen with all you need to make mealtime a bay breeze. Also on the 1st Floor is an adorable Reading/Relaxing Nook decorated with a shabby chic Coastal Flair, 2 Bedrooms, and a Full Bath. Bedroom 1 features a comfy Queen Bed, and Bedroom 2 has 2 Twins - b...