Riptide’s Crossing: Watch the ponies from our decks! Waterfront with pier too!

When you need to check off ALL of the boxes, you'll find everything you’re looking for at "Riptide's Retreat".

Named after one of Chincoteague's most beloved wild ponies Riptide, we've got everything you need to enjoy a spectacular vacation filled with memories that will last a lifetime. We provide all the essentials PLUS bikes, kayaks, beach/fishing cart, Bogg beach bags, beach towels, crab pots/traps, and more.

Come and enjoy the most amazing views from our multiple decks that look out over the Chincoteague Channel and the southern end of Assateague Island. You'll have unobstructed views of the Assateague Lighthouse as well as Little Beach both just a short kayak paddle away. There's plenty of parking for you and your guests too.

Want to bring your boat? We've got you covered. You'll have access to our private DEEP water dock LATER THIS SUMMER. Want to enjoy fresh crab for dinner? Use our crab traps and enjoy the freshest seafood ever.

We've even included an outdoor TV and dining area with seating for 10. You'll have a propane grill for your favorite feasts and there's a great spot with a firepit so you can make all the smore's you want for dessert.

If you're wondering where the famous pony swim takes place each July, it shouldn't surprise you that it takes place on PONY SWIM LANE. You'll have a FRONT ROW SEAT when you stay at Riptide's Retreat during that magical week in July. Literally there is NO OTHER vacation rental on the entire island of Chincoteague that will get you closer to the wild ponies on swim day.

But the BEST PART OF Riptide's Retreat is that you don't have to be there during Pony Penning week in July to see the ponies because you can see wild ponies year round as they graze in their natural environment just across the channel on the Chincoteague National Wildlife Refuge. If you want an up-close personal experience, you can paddle over with our kayaks or jump in your boat for a super quick ride.

By the way, the reason our home is called "Riptide's Retreat" is that Riptide is one of the most recognizable ponies in the southern herd and we're confident that you will likely see him and his band of beautiful mares during your stay. His dark chestnut coat contrasted by his beautiful blond mane makes him the "Fabio" of all ponies. I'll bet you will spot him during your visit.

As the owners of three vacation rentals on Chincoteague Island, this one packs the most punch and definitely has that WOW factor for guests as they arrive and gaze out at the water and Assateague Island.

Included with your reservation is an "Insider's Guide" to the island so you can maximize your time on this beautiful little island by the sea. We can't wait to see you come and enjoy.