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.
96 properties available
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
Welcome to Bonneau’s Beach House, where you will make lasting family memories where salty breezes, sandy toes, and unhurried days at the beach bring everyone together!This phenomenal End-Unit Townhome is located in a wonderful little community, Silver Sails. One of the most unique and wonderful features of this Neighborhood is that it has a spectac
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 week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
**Captain's Rest is now Flex-Stay ALL year long!**We travel not to escape Life, but so that Life doesn't escape us. It's so hard to find time to break away from the daily grind and spend time with those who matter most - but, we all know there's nothing more important. Make time to make Memories, because we've got the place for you! Welcome to Capt
Life’s a Beach - If you’re not barefoot, you’re overdressed….When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for just the right place - or just the right Experience, we should say - boy, do we have the place for you! K and S Paradise is nestled right in the heart of Chincoteague Islan
“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
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
Mmmmm., 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 week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
“To travel in the company of those we love is Home in motion.” ~ UnknownWhen was the last time you stepped away from the day to day to just BE together - to laugh, to play, to explore? With no appointments, no baseball practices, and no zoom calls, there’s nothing but time together, and nothing but incredible memories to be made, right here on Chin
“Travel not to escape Life, but so Life doesn't escape you.” ~ UnknownWelcome to The Feathered Nest - a tranquil retreat in the very heart of Chincoteague Island. This spectacular home is Brand New Construction in 2025, and will absolutely make your jaw drop! Tucked on a super quiet Lane off the beaten path, you’ll feel a million miles away from th
All you need is Love and the Beach…..Welcome to Love and Luck - possibly one of THE most adorable homes on Chincoteague Island! If you’ve been looking for the Chincoteague Charm of yesteryear, but need the Modern Amenities of today, you’ve come to the right place! They say that big things come in small packages, and Love and Luck is proof of that -
Travel - It leaves you speechless, then turns you into a Storyteller…..When was the last time you took a Vacation that took your breath away? If you’ve been looking for that one-of-a-kind Vacation Experience, we’d love to introduce you to ‘House on the Dune’ in the prestigious Wildcat Community on Chincoteague Island. This stunning Custom Home is 1
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