Chincoteague Rentals - Flex Stay Homes
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 Rentals with Flexible Stays so you can check-in on your schedule and not by a schedule set for you.
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88 properties available
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
Life’s at ease with a bay breeze…..Do you yearn to be so close to the water that you can take in that salty, sweet sea breeze while you sleep? Imagine fishing and crabbing only steps from your house - or having your Boat docked just behind the house - all the joys of living at the Water’s Edge.Welcome to Water’s Edge in the heart of Chincoteague Is
Our Memories of the Ocean live on, long after our footprints are gone….Making Memories - isn’t that what it’s all about? Escaping from the daily grind, and reconnecting with those who matter most. Kids grow up fast, and life is so short - the Beach is calling - and we have the perfect homebase for your next Chincoteague Island adventure….Welcome to
There’s no place like home ~ except for the Beach, that is!Welcome to Seabiscuit Surfside on Chincoteague Island, or as we like to call it, “Our Little Island by the Sea”! Seabiscuit Surfside offers you both - a beautiful home away from home, AND it’s less than 10 minutes from Assateague National Seashore, where our famous Wild Ponies roam free! As
Ahhh, Chincoteague Island—where the salty breeze of the marsh tickles your senses and wild ponies roam free, painting a picture straight out of a dream. Once you step foot on our little slice of paradise, it’s like leaving a piece of your heart behind. But let’s be real—life gets busy. Taking off for a full week every year? Not always easy. Maybe y
Trees listen to the Breeze; and then rustle its voice so beautifully….Looking for a getaway that makes you feel a million miles from the real world? Just imagine kicking back under the shade of tall Pine Trees - swaying in the breeze, while you listen to the Tree Frogs sing - pure bliss. Whispering Pines is not just a place to lay your head at nigh
Ready to have a ‘Shell of a Time’ on your next trip to our Little Island by the Sea?! You will absolutely fall in love with this beautiful Cottage on Chincoteague Island - tucked on a quiet street, but close to everywhere you want to be! Shell of a Time has all that you love about a quintessential Chincoteague Cottage, plus the Modern Amenities you
Longing to get away from it all and leave the busy world behind - even for a just a little while? We cannot think of a better getaway than lovely Fish On on Chincoteague Island. This beautiful Duplex that sleeps 6 more than comfortably is in the very heart of our special Island. Located on Ridge Road, only steps from famous Pony Swim Lane, you can
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ocean Pearl Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Street Restaurants, Shops, and Robert Reed Waterfront Park - home to THE most ama
“Not all who wander are lost…..”Welcome to Lily Pad 2 in the very heart of Chincoteague Island! If you’ve been looking for the perfect place to “get lost”, yet still be close to everywhere you want to be, this is the place for you! Brand New Lily Pad 2 sits tucked down a quiet Lane, and is the sister-house to Lily Pad on Wayne Road, sitting almost
Have you ever asked yourself what the purpose of life is? Here at Seaside, we believe it’s all about spending time with those that matter most, and making memories you’ll cherish forever. And if you can make the time, we’ve got the most amazing home to tell you about…..Welcome to The Porpoise of Life in the very heart of Chincoteague Island. This
Ahhh, Chincoteague Island—where the salty marsh breeze greets you, and wild ponies roam Assateague as if they’re welcoming you home. One trip here, and it’s love at first sight—it’s the kind of place that sticks with you forever. But let’s face it, life’s a whirlwind, and carving out a whole week to escape isn’t always in the cards. Maybe you’re mo
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