Chincoteague Rentals - Flex Stay Vacations
Here at Seaside Vacations, we understand how busy life is, and that you can't always get away for a full week. That's what we LOVE about our Flex Stay Program—arrive when you want, depart when you want, the world is your Oyster (it's a Chincoteague thing)! The homes in our Flex Stay Program have either a 2 or 3 night minimum all year long, not just the Off-Season! As always, we're standing by ready to help you find just the right home for your next Beach Break!
Browse these amazing Chincoteague Island vacation rentals with Flexible Stays, so you can check-in on your schedule.
110 properties available
“Live in the sunshine, swim in the sea, drink the wild air.” ~ Ralph Waldo EmersonThere’s something about a day at the Beach - the warm sun on your face, the salty, sweet sea breeze, the sound of the Laughing Gulls - not to mention our Famous Wild Ponies - pure heaven! When was the last time you escaped the day to day, just to relax, rejuvenate, an
Ava’s Beach Cottage - Relax, Rejuvenate, and Reconnect…..Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ava’s Beach Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern
There is only one thing more precious than our time, and that is who we spend it on….Life is short - we live in a world where we’re always rushing - even when there’s no rush! We have to force ourselves to slow down - to stop and smell the flowers - or even better, Mother Ocean! If you’ve been longing to get away with those who matter most, we have
Welcome to Fletcher House #8 on Willow Street! The Fletcher House Cottages have been helping families make amazing Chincoteague Memories for decades! Once part of the The Sea Shell Motel, these cottages are now part of our Seaside Vacations’ Family! And, Fletcher House Guests have access to the Outdoor Pool at the Sea Shell Motel nearby!This adorab
Welcome to Chris' Cottage 2!Tucked away in a peaceful setting just a short stroll from the Sea Shell Motel and the beach, Chris’ Cottages offer the perfect blend of comfort, convenience, and classic Eastern Shore charm. This property features three identical cottage-style units, thoughtfully updated and designed for a relaxing coastal getaway. All
Memories made together last a lifetime…..Welcome to Oyster Bay Oasis in ever-popular Oyster Bay I on Chincoteague Island - the perfect home base for your family’s next adventure! Only 5 minutes from Assateague National Seashore, where our Wild Ponies roam free, this adorable home has all the quintessential Chincoteague Charm you love, plus the mod
Assateague Inn 102 has been completely renovated for 2025, and is beachy and beautiful - check it out!Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole
Welcome to Fletcher House #7 on Willow Street! The Fletcher House Cottages have been helping families make amazing Chincoteague Memories for decades! Once part of the The Sea Shell Motel, these cottages are now part of our Seaside Vacations’ Family! And, Fletcher House Guests have access to the Outdoor Pool at the Sea Shell Motel nearby!This adorab
Sea Glass - All you need is Sunshine and Saltwater....Much like finding sea glass as you stroll on the Beach, it’s the little things in life that often make the biggest difference. Time with family - a lazy day on the beach, catching crabs off the Dock, telling stories around a campfire - these are the little things that amazing Vacation Memories a
Welcome to Dolly's Place 5!Tucked away in a peaceful setting just a short stroll from the Sea Shell Motel and the beach, the Cottages offer the perfect blend of comfort, convenience, and classic Eastern Shore charm. This property features 2 Cottages, both sitting behind Dolly’s House. All of this, and just minutes from one of the most pristine and
Welcome to Mariner’s Light - a lovingly restored historic home that blends timeless Chincoteague charm with fresh, shabby-chic coastal style. Thoughtfully renovated from top to bottom, this adorable vacation retreat feels both nostalgic and beautifully new—where original character meets breezy modern comfort. Y’all are going to absolutely love this
Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is
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