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
May you always have a shell in your pocket, and sand in your shoes…..Sandy Bottoms - the name alone stirs up fond memories of family vacations from long ago. This wonderful 4 Bedroom Home is brand new to the Seaside Vacations’ Family, and we couldn’t be happier - and it’s ready to make your Vacation Dreams come true!With Classic Coastal Cape good l
Hot HOT 12
Sandy Bottoms
House
$128 - $425 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 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 24
Painted Pony Cottage
House Pet Friendly
$75 - $224 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 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 18
One Particular Harbour
House Pet Friendly
$110 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 10 guests
Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Little Red Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Str
Hot HOT 19
Little Red Cottage
House
$100 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 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
Hot HOT 16
Heron Creek
Town House Pet Friendly
$150 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Have you always wanted to Vacation on Chincoteague Island, but couldn't bear the thought of 4 of you in a hotel room? Love the idea of a Vacation Home, but don't want to break the bank? Look no further than Sunrise Serenade at Sea Tag Lodge, formerly "Sea Tag # 24". These fabulous Condos are located directly on the Assateague Channel with some of t
Hot HOT 9
Sunrise Serenade
Condominium
$65 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for just the right place - or just the right Experience, we should say - boy, do we have the place for you! Coquina Cottage is nestled right in the heart of Chincoteague Island, and combines all the charm of yesteryear you love, with the
Hot HOT 12
Coquina Cottage
House
$125 - $299 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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
Hot HOT 21
The Pearl at Grand Bay
Town House Pet Friendly
$85 - $300 / per night
Bedrooms 2 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 12
Assateague Inn 203-S
Condominium
$45 - $363 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 19
Vineyard Cove
House
$175 - $475 / per night
Bedrooms 3 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 12
Assateague Inn 209-S
Condominium
$45 - $363 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sunsets are proof that no matter what happens, every day can end beautifully - and there is no better place to take in one of our famous Chincoteague Sunsets than fabulous Waterfront Wonder (formerly Sunset Foals). With gorgeous Newly Refinished, but still Historic, Hardwood Floors, and other upgrades, Waterfront Wonder still oozes the quintessenti
Hot HOT 26
Waterfront Wonder
House Pet Friendly
$112 - $535 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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