Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

Browse over 150 Chincoteague Island Rentals, all at the Best Rates

Welcome to beautiful Chincoteague Island! Are you ready for a vacation away from the big city and crowded beach resorts? A Chincoteague Vacation Rental means that there are no high-rises, boardwalks, or traffic jams to interfere with your relaxation. We offer beautiful rentals to fit any family size or group gathering, all at the lowest rates around. Come see the wonder of Chincoteague Island, include famous events such as the Pony Swim!

Seaside Vacations offers so many wonderful vacation house rentals from Chincoteague Island to the Mainland. Select from our large choice of Chincoteague Waterfront Vacation Rentals or Rentals with Pools.


Popular Chincoteague Island Rentals

House Rentals | Condo Rentals | Waterfront Rentals | Rentals with Pools | Pet Friendly Rentals | Communities


Properties Available 170 properties available
History. Charm. Allure. Just a few of the things that make The Inn at Poplar Corner such a special Island Retreat. This incredible 5 Bedroom and 5 Bath Home has quite a story to tell. In its past life, it was a wildly popular Bed and Breakfast. A Local Family owned The Watson House, and was so blessed with Guests they bought two other Cottages in t
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The Inn at Poplar Corner
House
$170 - $600 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 10 guests
Salty air breezes and the sweet serenity of pond-front living await you at The Pearl at Grand Bay. This Newly Remodeled End Unit Townhome has it all - magnificent Water Views, and a stunning interior. Located on the ever-popular East Side, you can have the Chincoteague Vacation you’ve been dreaming of at a very family-friendly price tag - and even
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The Pearl at Grand Bay
Town House Pet Friendly
$85 - $300 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 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
Hot HOT 19
Deja Blue
House
$90 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Stunning Updates for 2023!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 shor
Hot HOT 30
Assateague Inn 111-2R
Condominium
$45 - $425 / 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 16
Kindred Tides
House
$125 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Have you ever asked yourself what the purpose of life is? Here at Seaside, we believe it’s all about spending time with those that matter most, and making memories you’ll cherish forever. And if you can make the time, we’ve got the most amazing home to tell you about…..Welcome to The Porpoise of Life in the very heart of Chincoteague Island. This
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The Porpoise of Life
House
$150 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
The Ocean stirs the heart, inspires imagination, and brings joy to the soul….Welcome to The Good Life on Ocean - the perfect homebase for your family’s Chincoteague Island Adventures! Only 5 minutes from Assateague National Seashore, where our famous Wild Ponies roam free, this adorable home has all the quintessential Chincoteague Charm you love, p
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The Good Life on Ocean
House
$110 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Isn't it time for a new romance.....with Life?! A visit to fabulous Seaside Rendezvous is certainly the place to begin.  This phenomenal End-Unit Townhome is located in a wonderful little community, Silver Sails. One of the most unique and wonderful features of this Neighborhood is that it has a spectacular Community Swimming Pool for you to enjoy
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Seaside Rendezvous
Town House
$137 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Bliss by the Bay - If you’re wearing flip flops, you’re overdressed!There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at Bliss by the Bay in beautiful Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly
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Bliss by the Bay
House
$125 - $375 / 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 9
Assateague Inn 204-S
Condominium
$45 - $430 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Heron Creek - Relax, Rejuvenate, and Reconnect…..Life is busy - schedules, school, meetings, and games - it’s nonstop. When was the last time you spent time with those who matter most simply playing - relaxing - giggling - making memories sure to last a lifetime?If this is what you’ve been yearning for, just wait til we tell you about fabulous Hero
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Heron Creek
Town House Pet Friendly
$150 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 45
Eventide
House
$125 - $295 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests

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