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 Rentals with Flexible Stays, so you can check-in on your schedule and not by a schedule set for you.
93 properties available
Collect Memories, not things…..Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chinco
The Robinson Family Beach House is now dog friendly with a $100 Pet Fee!There is no time to be bored in a world as beautiful as this….Welcome to The Robinson Family Beach House on our little slice of Heaven, Chincoteague Island. Located on ever-popular North Main, you'll enjoy the peace and quiet, yet still be close to everywhere you want to be. Th
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
Looking for an incredible Chincoteague Island Vacation Experience? You just found it at Sea Treasure - a beautiful Duplex that sleeps 6 more than comfortably in the very heart of our special Island. Located on Ridge Road, right next to famous Pony Swim Lane, you can relax on your Screened Porch and take in amazing Views of Assateague Island and our
Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our little piece of Paradise - the Wild Ponies running free, Saltwater Cowboys leading the way, the Saltiest, Sweetest Oysters to be found, and hands down THE best Sunsets over the water. Guess what? It's ALL true - isn't it time you di
Beachgrass Bungalow - High Tides and Good Vibes….The best things in Life are the people we love, the places we’ve been, and the memories we make along the way…..Life is busy - plain and simple. Work, meetings, schedules, lessons - pretty much chaos - all the time! This makes breaking away from the day to day more important than ever. Pack a bag, gr
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
Sky above, Sand below, Peace within….Life is short - and busy - OH, so busy. When was the last time you grabbed those who matter most and left it all behind, even if just for a few days?! If you’ve been longing for a Beach Break, we’ve got the perfect place for you, right here in the very heart of Chincoteague Island! Welcome to The Virginia Lee -
“Travel is the only thing that leaves you speechless, then turns you into a storyteller.” ~ Ibn BattutaHave you been longing for a Vacation Experience that your family won’t soon forget?! Life is so busy - work, school, games, and meetings steal so much precious time from us. It’s so important to grab those who matter most, and just BE together. An
Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Little Red Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Str
Welcome to Waterfront Sunsets - Sunsets are proof that no matter what happens, every day can end beautifully…..This adorable Efficiency Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel, the Causeway, and the Chincoteague Channel. Perfect for a Romanti
“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
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