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 85 properties available
Sea Breeze - Life’s at ease with an Ocean Breeze…..Close your eyes and imagine breathing in that salty, sweet air - the sound of the Gulls, the Watermen harvesting Oysters - you’re beginning to relax, and you’re not even here yet! This is a feeling deep in your soul - this is Sea Breeze…..Located on Marsh Island, you'll have amazing Views of both B
Hot HOT 13
Sea Breeze
House
$275 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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
Hot HOT 10
Assateague Inn 104-S
Condominium
$45 - $329 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to Assateague Inn 107 in the heart of Chincoteague Island at the The Assteague Inn. The Inn is a long time favorite of Beach Lovers, and sits less than 5 minutes from Assateague National Seashore, where our Wild Ponies roam free!What makes Assateague Inn 107 different from the other Suites at this beloved building? It’s the ONLY Suite that
Hot HOT 13
Assateague Inn 107-A
Condominium
$65 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sugar Shores - Your next Vacation can be both Salty and Sweet!When was the last time you had a Vacation that took your breath away? It’s the perfect combination of the right Destination, the right Vacation Home, and the perfect Location. Sugar Shores on beautiful Chincoteague Island is all of that and more, and only a few minutes from Assateague Na
Hot HOT 16
Sugar Shores
House Pet Friendly
$125 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
“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
Hot HOT 37
Eventide
House Pet Friendly
$125 - $375 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 10 guests
Beach More, Worry Less…..If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New Addition to our Seaside Family has it all - that quintessential Chincoteague Charm you love, the Modern Amenities you want and need, and a fabulous Mid-Island Location - close to everywhere you want to be!Shore to Please is tucked on
Hot HOT 17
Shore to Please
House Pet Friendly
$95 - $350 / per night
Bedrooms 5 bedrooms
Bathrooms 1 bath
Guests 10 guests
Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague Lovers for years. Located less than 5 minutes from Assateague National Seashore, and allowing short stays all year long, it’s the perfect Vacation getaway for singles, couples, or small families. Assateague Inn 100-2R is actually
Hot HOT 22
Assateague Inn 100-2R
Condominium
$45 - $370 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
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
Hot HOT 65
Oyster Bay Oasis
House Pet Friendly
$99 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
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
Hot HOT 12
Seabiscuit Surfside
House
$99 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
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 -
Hot HOT 13
Love and Luck
House
$99 - $426 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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
Hot HOT 25
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
Hot HOT 16
Assateague Inn 205-S
Condominium
$45 - $324 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

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