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 71 properties available
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
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Sugar Shores
House Pet Friendly
$125 - $300 / 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 17
Assateague Inn 107-A
Condominium
$45 - $408 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ocean Pearl Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Street Restaurants, Shops, and Robert Reed Waterfront Park - home to THE most ama
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Ocean Pearl Cottage
House Pet Friendly
$95 - $250 / per night
Bedrooms 1 bedroom
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
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Assateague Inn 208-S
Condominium
$45 - $358 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 15
Assateague Inn 109-S
Condominium
$45 - $352 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Life is good, but Island Life is better!Looking for a Beach Break that will take your breath away, yet not break the bank? Welcome to The Teague House on peaceful and serene Marsh Island! This Newly Renovated Townhome in Captain’s Quarters Townhomes has it all, and is just a stone’s throw from our beautiful Little Island by the Sea!As you take the
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The Teague House
Town House
$85 - $350 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Life is good - but Island Life is better!Welcome to The Salty Crab in the very heart of Chincoteague Island! This gorgeous Brand New Home is nestled on Church Street, just a short stroll from our famous Farmers Market and Downtown Historic Main Street’s many Shops and Restaurants. Robert Reed Waterfront Park is also only steps away and home of the
Hot HOT 86
The Salty Crab
House Pet Friendly
$99 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sitting Waterfront on Eel Creek, you'll enjoy lovely Views!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
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Assateague Inn 213-2R
Condominium
$45 - $292 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
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, grab those who matter most, and get ready to make s
Hot HOT 24
Kindred Tides
House
$125 - $450 / per night
Bedrooms 4 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 13
Assateague Inn 103-S
Condominium
$45 - $354 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Wonderview 208 ~ Take the Journey to enjoy the View…..Life gets busy - work, kids, appointments, pets - it never seems to stop. This makes it more important than ever to take time to stop and smell the roses - or more appropriately, the salty, sweet sea breeze. If you can make the time, we most definitely have the place….Welcome to fabulous Wonderv
Hot HOT 23
Wonderview 208
Condominium
$100 - $375 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Painted Pony Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chinc
Hot HOT 23
Painted Pony Cottage
House Pet Friendly
$75 - $224 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests

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