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.



Properties Available 178 properties available
At the Beach, life is different. Time doesn't move hour to hour, but with the flow of the Ocean. We live by the currents, plan by the tides, and follow the sun. When is the last time you can say you had a day like this? Now is the time - grab the kids, the dogs, and the horses - that’s right - Seahorse Shanty is Dog AND Horse Friendly! Up to 2 well
Hot HOT 12
Seahorse Shanty
House Pet Friendly
$150 - $579 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 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 20
Shell of a Time
House
$95 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
The very definition of ‘Amistad’ is friendship - and that suits this beautiful home so well, as you’ll feel like you’re visiting a long, lost friend on our Little Island by the Sea. You’ll love making unforgettable family memories in this charming historic home that has graced Chincoteague Island with its presence since the early 1900’s. With the q
Hot HOT 27
Amistad
House Pet Friendly
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Looking for the perfect beach break close to everywhere you want to be? The Assateague Inn is a long time favorite of Chincoteague Island Lovers, and sits less than 5 minutes from the Beach! Assateague National Seashore is one of the most visited beaches in America - after a visit, you will understand why! Home of our famous Wild Ponies, our pristi
Hot HOT 8
Assateague Inn 103-S
Condominium
$45 - $348 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Of all the paths you take in life, make sure a few of them are sandy…..Welcome to ‘Paradise’ on dreamy Chincoteague Island - it’s not just a vacation home, it’s a feeling - relax, rejuvenate, and reconnect with those who matter most at this gorgeous Waterfront Townhome nestled directly on the Chincoteague Bay.Tucked away in the perfect location on
Hot HOT 13
Paradise
Town House
$145 - $549 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 13
Assateague Inn 104-S
Condominium
$45 - $346 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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 12
Sea Treasure
Town House
$85 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
There’s only one thing more precious than our time, and that is who we spend it on. Even in today’s world, it isn’t always easy to find true quality time with those who matter most. There are Zoom meetings and virtual lessons - the days are still demanding, and perhaps even more stressful than ever. Making that special time for nothing more than ‘t
Hot HOT 15
Hudson House
House
$150 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... Welcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination t
Hot HOT 17
Whelks on Willow
House
$140 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous Pier Pressure in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom Waterfront Dream Home has something for everyone in the family. Located at the water’s edge dir
Hot HOT 25
Pier Pressure
House
$125 - $325 / 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 18
Assateague Inn 206-S
Condominium
$45 - $349 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Happy Pines has some great updates including New Floors throughout and updated Bathrooms!As you turn onto Pine Creek Drive, you will feel the hustle and bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Bedroom, 2
Hot HOT 19
Happy Pines
House
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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