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 70 properties available
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
Hot HOT 9
Sea Treasure
Town House
$85 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
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
Hot HOT 25
Whispering Pines
Town House Pet Friendly
$145 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 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
Hot HOT 17
Starbright Cottage
House Pet Friendly
$125 - $400 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 9 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
Hot HOT 14
High Tide Hideaway
House Pet Friendly
$150 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 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 36
Shore to Please
House Pet Friendly
$95 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 1 bath
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
Assateague Inn 206-S
Condominium
$45 - $430 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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
Hot HOT 25
Beachgrass Bungalow
House Pet Friendly
$99 - $285 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Sea Glass - All you need is Sunshine and Saltwater....Much like finding sea glass as you stroll on the Beach, it’s the little things in life that often make the biggest difference. Time with family - a lazy day on the beach, catching crabs off the Dock, telling stories around a campfire - these are the little things that amazing Vacation Memories a
Hot HOT 43
Sea Glass
House
$275 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 13
Assateague Inn 107-A
Condominium
$45 - $496 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
We are big believers that every Home has a story.......a story rich in happiness and sadness, struggles and successes - that creates its very essence. The C-Ray Cottage has a story you will love.......This adorable Bayfront Waterman's Cottage exudes that quintessential Chincoteague Charm. The C-Ray Cottage is the former working office of C. Ray Jes
Hot HOT 18
The C-Ray Cottage
House
$150 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
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
Hot HOT 10
Shell of a Time
House
$95 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 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 11
Assateague Inn 109-S
Condominium
$45 - $425 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

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