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.

Pony Swim Crossing - Chincoteague Island is calling….. “To sit in silence at the shore, watch the waves and hear the surf, is to appreciate the very breath and heartbeat of the earth.” ~ Unknown Isn’t it time to break away from the daily grind? The stress, the traffic, and oh, “schedules” - aren’t we all just a little too “scheduled” in life? Grab those who matter most, pack a bag, and head on down to our little slice of heaven. Pony Swim Crossing sits perched on the Assateague Channel with captivating Views of the Channel and Assateague Island. Tucked away on the ever-popular East Side on Pony Swim Lane, you are literally overlooking where our famous Saltwater Cowboys swim our Wild Ponies over during our Annual Pony Swim. There’s truly no better backdrop to your next Island Adventure. This adorable Townhome is part of our Flex Stay Program, so no worries if you can’t get away for a full week! Arrive when you want, depart when you want - it’s YOUR Vacation, after all! Beautifully decorated and furnished with a warm Coastal Flair, Pony Swim Crossing is so welcoming, and is perfect for a small family or a few couples to share. As soon as you walk through that door, the wonderful Water Views are center stage - kick off your flip flops and let the fun begin! You’ll love kicking back in the Living Area after a fun-filled day on the water, and enjoying Free WiFi and Flat Screen TV. Dressed in Coastal Blues and Grays, its palette is pulled from Nature itself. Sink into the comfy Sectional after a fun-filled day at the Beach, or step outside onto the Covered Deck to take in Channel Views that will leave you breathless. Overlooking Assateague Island and Assateague Light, the beauty is hard to describe - you may even see ponies grazing across the Channel in the Marsh. Mealtime will feel like a bay breeze in the well-stocked Kitchen! Dine in the comfort of Central AC, or on your Waterfront Balcony, Al-Fresco Style. Not one to cook on Vacation? Stroll or take...