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 55 properties available
Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, you'll be tucked away in a quiet location in the heart of our Island, yet close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the
Hot HOT 10
Breezy Corner
Chincoteague, VA
$90 - $329 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
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
Hot HOT 8
Assateague Inn 204-S
Condominium
$50 - $285 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Assateague Inn 102 had a facelift for 2022, and is beachy and beautiful - check it out!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
Hot HOT 16
Assateague Inn 102-S
Studio
$50 - $249 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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. The Attractions of Historic Main Street with so many quaint Shops and Rest
Hot HOT 15
The Robinson Family Beach House
House
$135 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 14
Assateague Inn 109-S
Condominium
$50 - $286 / per night
Bedrooms 1 bedroom
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
Hot HOT 125
Starbright Cottage
House Pet Friendly
$110 - $452 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 9 guests
Breakaway - Chincoteague Island is calling…..**PIER AND BOAT SLIP NOT CURRENTLY AVAILABLE DUE TO REPAIRS**“To sit in silence at the shore, watch the waves and hear the surf, is to appreciate the very breath and heartbeat of the earth.” ~ UnknownIsn’t it time to break away from the daily grind? The stress, the traffic, and oh, “schedules” - aren’t w
Hot HOT 35
Breakaway
Chincoteague, VA
$100 - $431 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
** Junes Cottage has some great updates for 2022!**Have you been yearning to relax - reconnect - and have a little fun with those who matter most? It's time - and the place is June's Cottage on Chincoteague Island. This lovely Historic Home is tucked away on a quiet Lane, away from the hustle and bustle, yet close to everywhere you long to be - you
Hot HOT 15
Junes Cottage
Chincoteague, VA
$75 - $317 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 32
Assateague Inn 100-2R
Condominium
$56 - $314 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague I
Hot HOT 24
The Happy Crab
Town House
$120 - $524 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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
Hot HOT 34
Pony Paradise
House Pet Friendly
$105 - $431 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Just give me the Sea, and a little Cottage just to be…..Work, meetings, school, traffic, homework, repeat - right?! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Take in that salty, sweet sea b
Hot HOT 24
Serendipity
Town House
$110 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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