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.

Search and book online today!


Properties Available 75 properties available
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
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Waterfront Sunsets
Condominium
$60 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 3 guests
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
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Assateague Inn 206-S
Condominium
$45 - $348 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
At the Beach, life is different. Time doesn't move hour to hour, but with the flow of the Ocean. We live by the currents, plan by the tides, and follow the sun. When is the last time you can say you had a day like this? Now is the time - grab the kids, the dogs, and the horses - that’s right - Seahorse Shanty is Dog AND Horse Friendly! There is a n
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Seahorse Shanty
House Pet Friendly
$150 - $741 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
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
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Assateague Inn 204-S
Condominium
$45 - $348 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
*Assateague Inn 211 has had some great updates for 2024 including new Flooring and a totally new bathroom including shower with grab bars, some new furnishings, and new art! 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 w
Hot HOT 20
Assateague Inn 211-S
Condominium
$45 - $348 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Deja Blue - there is no color quite like this…..You know that feeling when you see the Ocean and all your worries just wash away? That’s the feeling you get as soon as you walk through the French Doors at Deja Blue on Chincoteague Island. This adorable Cottage oozes that quintessential Chincoteague Charm you love, plus has the Modern Amenities you
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Deja Blue
House
$90 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Reach for the Stars on your next Chincoteague Island Vacation…..Welcome to whimsical Starbright Cottage on beautiful Chincoteague Island! This adorable 4 Bedroom home is not only in an amazing mid-Island location, it welcomes your whole family - including your friendly Dog! Starbright Cottage has the allure of a bygone era, combined with the modern
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Starbright Cottage
House Pet Friendly
$125 - $400 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 9 guests
Bella Vista - Everything is better with a Water View…..Welcome to Sunset Bay 319 - Bella Vista - at fabulous Sunset Bay Villas on the Chincoteague Bay. Bella Vista, which is Italian for ‘beautiful View’, more than lives up to its name with stunning Direct Bayfront Views all around. These gorgeous condos sit directly on the Bay with spectacular View
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Sunset Bay Villa 319 - Bella Vista
Condominium
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
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
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Water's Edge
Town House
$100 - $400 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
“Rainbows and Mermaids are proof that imagination and beauty go hand in hand.”Welcome to The Mermaid Lounge on Chincoteague Island. An absolutely adorable and affordable Beach getaway tucked on the ever-popular East Side - close to everywhere you want to be!If you’re not familiar with the East Side, imagine driving down a quiet road that hugs the s
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The Mermaid Lounge
Town House
$99 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Good Vibes happen on the Tides…..Welcome to High Tide Hideaway - Brand New Construction in July 2023! Tucked in the very heart of our Little Island by the Sea on Church Street, you’re close to everywhere you want to be. Downtown Main Street Shops and Restaurants are just a short stroll away, as is our famous Farmers Market! You’ll love wandering do
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High Tide Hideaway
House Pet Friendly
$150 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
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
Hot HOT 20
Assateague Inn 100-2R
Condominium
$45 - $389 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests

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