Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

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

Welcome to beautiful Chincoteague Island, also known as Our Little Island by the Sea! 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.



Properties Available 176 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 63
Sea Treasure
Town House
$85 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
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
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Breezy Corner
House
$90 - $285 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 7 guests
Collect Memories, not things…..Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chinco
Hot HOT 28
Teal Cottage
House
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 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 15
Assateague Inn 104-S
Condominium
$45 - $299 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Ahhh, Chincoteague Island—where the salty marsh air fills your lungs, and wild ponies casually stroll Assateague like they own the place (because, let’s be honest, they kind of do). One visit, and you’re hooked for life. But we get it! Life moves fast, and sneaking away for a full week every year isn’t always in the cards. Maybe you’re more of a W
Hot HOT 18
Assateague Inn 202-S
Condominium
$45 - $303 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Looking for somewhere truly special to spend your Chincoteague Island Family Vacation this year? Look no further, as special doesn't even begin to describe the tranquility and beauty of waterfront Family Tides. This adorable home is located directly on Lewis Creek's deep water, so by all means, bring the boat, kayaks, jet skis, or water toy of choi
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Family Tides
House
$135 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 18
Kindred Tides
House Pet Friendly
$125 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Assateague Inn 106 is newly renovated with New Flooring, Cabinets, Renovated Bathroom, and Fresh Paint - it's gorgeous!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
Hot HOT 14
Assateague Inn 106-S
Condominium
$45 - $299 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Travel - It leaves you speechless, then turns you into a Storyteller…..When was the last time you took a Vacation that took your breath away? If you’ve been looking for that one-of-a-kind Vacation Experience, we’d love to introduce you to ‘House on the Dune’ in the prestigious Wildcat Community on Chincoteague Island. This stunning Custom Home is 1
Hot HOT 50
House on the Dune
House
$325 - $800 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Life is a collection of Moments….Longing for a new Experience - a different kind of Beach Getaway? Let us introduce you to a truly ‘Hidden Gem’ in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia!Captain’s Cove is only 25 short minutes by boat or car from Chincoteague Island and Assateague National
Hot HOT 14
Hidden Gem
House
$145 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Take a Vacation that makes you forget to check your cell phone….Looking to leave the real world behind - just for a few days? Grab those who matter most, and clear your calendar - Caribbean Ketch is waiting for you! This charming home is located in the ever-popular Piney Island, which happens to be the closest community to Assateague National Seash
Hot HOT 26
Caribbean Ketch
House
$125 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 15
Starbright Cottage
House Pet Friendly
$125 - $400 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 9 guests

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