Chincoteague Island Vacation Rentals

Chincoteague Island Vacation Rentals

Browse over 100 Chincoteague 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 170 properties available
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 9
Teal Cottage
House
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 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 5
Assateague Inn 205-S
Condominium
$45 - $284 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 13
Hudson House
House
$150 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
GREAT UPDATES FOR 2023!! Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 18, located in the very heart of Chincoteague Island. This lovely Townhome is convenient to everywhere you want to be on our beautiful Island, yet a quiet and peaceful Retreat at the day's end. And, there's
Hot HOT 14
Eastwinds 18
Town House Pet Friendly
$70 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Cove’s Point - Of all the paths you take in life, make sure a few of them are sandy…….When was the last time you had a vacation that took your breath away? If this is what you’ve been craving, Cove’s Point is the place for you. Located in gorgeous Captain’s Cove Golf and Yacht Club - one of the best kept secrets on the Eastern Shore of Virginia, yo
Hot HOT 8
Coves Point
House
$135 - $385 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague I
Hot HOT 8
The Happy Crab
Town House
$120 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Just give me the Sea, and a little Cottage just to be…..Work, meetings, school, traffic, homework, repeat - right?! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Take in that salty, sweet sea b
Serendipity
Town House
$110 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 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 10
East Side Breezes
House
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Have you been yearning to relax - reconnect - and have a little fun with those who matter most? It's time - and the place is June's Cottage on Chincoteague Island. This lovely Historic Home is tucked away on a quiet Lane, away from the hustle and bustle, yet close to everywhere you long to be - you'll truly be living amongst the Locals. Large and s
Hot HOT 7
Junes Cottage
House
$75 - $295 / 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 25
Starbright Cottage
House Pet Friendly
$125 - $400 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 9 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
Assateague Inn 203-S
Condominium
$45 - $283 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to Albion and the best Chincoteague Island Vacation you have ever had! This phenomenal, one-of-a-kind dream home is located on Willow Street, right in the heart of the island, and near everywhere you want to be. Lush, tropical landscaping will welcome you as you pull into the custom circular driveway, with parking for 3 cars. This spectacul
Hot HOT 8
Albion
House
$126 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests

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