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.

The Happy Crab - Where dreams are made of Sun and Sand….. There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague Island to make Memories that you'll treasure forever. The Happy Crab is a Duplex Home that sleeps 6 more than comfortably, and is located in desirable Piney Island, the closest community to Assateague National Seashore. Ride your bike to the Beach, Dining, Activities, and more! You'll love returning to this tranquil Waterfront Community lined with whispering Pines, which even has its own Kayak Launch area. Sitting directly on the Assateague Channel, you have incredible Views of both the Channel and Assateague Island right from your two-levels of decking. With a Pier shared with only one other home, you'll love fishing and crabbing in your own backyard - or harvest some of our famous Oysters at low tide, only steps from the shoreline. There's also super-easy access to launch your kayak or canoe, and if you're bringing your boat, you can tie it up right at the Pier. This adorable Waterfront Home has it all - including the warmth and comfort of a true family home. As you pull into the driveway, you know you've made the right choice - the Pine Trees swaying and Tree Frogs singing couldn't be more welcoming - and ahhh, that salty, sweet breeze. Climbing the stairs to the 1st Floor, you'll love the Open Living Area with plenty of comfy seating, Flat Screen Cable TV, and stunning Views galore. With 2 Waterfront Decks, a Waterfront Screened Porch, and 2 other Decks, you won’t know where to begin and end every amazing Vacation Day - so many choices! The Happy Crab sits high, maximizing every gorgeous glimpse of our beautiful bay and Assateague Island. Down the Hall, there's a huge Dining Area with a table that seat...