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 181 properties available
Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you've been longing for - tucked away on a quiet lane in the heart of our tiny Island. George's Retreat is in the perfect location, just off of Maddox Boulevard, aka the Beach Road - you can walk or ride your bike to many, Restaurants
Hot HOT 12
Georges Retreat
House
$75 - $240 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Life is simple….just add water!The way we live today is crazy - we’re always in a hurry! Work, school, meetings, repeat. It’s so hard to find the time to gather those who mean the most to simply BE together. This is where “Stacked Deck” comes in - this home was made for making family memories together!This spectacular Waterfront Home is Brand New a
Hot HOT 13
Stacked Deck
House
$175 - $600 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Ocean air, salty hair, not a care, take me there……Life is so busy - our days are filled with one commitment after another. Isn’t it time for a Beach Break - time to reconnect and rejuvenate with those who matter most? If you can make the time, we have the perfect Vacation Destination for you at Vineyard Cove on Chincoteague Island….Vineyard Cove si
Hot HOT 15
Vineyard Cove
House
$175 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Wind Rose has some great updates including a New Outdoor Shower and Arcade1Up Pac-Man Legacy Machine with 12 different games! Now Dog Friendly with a $100 Pet Fee each!Wanderlust - "a strong desire or urge to wander or travel and explore the world." Have YOU experienced the beauty and wonder of Chincoteague Island yet? Beautiful Wind Rose is the p
Hot HOT 13
Wind Rose
House Pet Friendly
$100 - $275 / 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 11
Assateague Inn 100-2R
Condominium
$45 - $374 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Welcome to Bliss on the Bay - leave your troubles at the door, you won't be needing them here! This super charming 1 Bedroom/1 Bath Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel and the Chincoteague Channel. Perfect for a Romantic Getaway or a smal
Hot HOT 10
Bliss on the Bay
Condominium
$75 - $265 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Changes in Latitude, Changes in Attitude…..As Jimmy Buffet would say, welcome to One Particular Harbor! And just as his music has a way of relaxing and rejuvenating us, so does this fabulous Vacation Home in the heart of Chincoteague Island. This absolutely adorable Cottage is not only Pet Friendly (see restrictions below), it’s in an awesome locat
Hot HOT 19
One Particular Harbour
House Pet Friendly
$110 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 10 guests
Welcome to Beach Blessing - a beautiful Chincoteague Island Vacation Home ready to make your Vacation Dreams come true! This breathtaking New Home is located on Boothe Street - a quiet and serene location nestled between Main Street and Willow, yet close to everywhere you want to be. You can easily walk or ride your bike to the Carnival Grounds, Re
Hot HOT 11
Beach Blessing
House
$125 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Sky above, Sand below, Peace within…..Here at Seaside, we believe that finding the “perfect” Vacation Home is so much more than merely finding a place to lay your head at night. We are all about “Experiences” ~ and a stay at ‘East Side Breezes’ is just that ~ a blissful Experience that will be treasured by your family for years to come. This specta
Hot HOT 11
East Side Breezes
House
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or w
Hot HOT 13
Sunset Bay Villa 111
Condominium
$125 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, and the best Sunsets to be found. Lounge by the Bayfront Pool and watch Herons and Egrets frolic over the water. Try your hand at crabbing or fishing from the Community Dock - or w
Hot HOT 19
Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Memories at the Beach last a lifetime…..Hoping to land the big one this year for your Chincoteague Island Vacation? Look no further than adorable “Catch of the Day” on super quiet and peaceful Tim Lane, just off Deep Hole Road, in the very heart of Chincoteague Island!This delightful Duplex sits tucked at the end of the Lane, surrounded by peaceful
Hot HOT 12
Catch of the Day
Town House
$110 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests

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