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 171 properties available
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 “Dock Holiday” comes in - this home was made for making family memories together. This spectacular Waterfront Home is Brand New
Hot HOT 38
Dock Holiday
House
$145 - $550 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
We are big believers that every Home has a story.......a story rich in happiness and sadness, struggles and successes - that creates its very essence. The C-Ray Cottage has a story you will love.......This adorable Bayfront Waterman's Cottage exudes that quintessential Chincoteague Charm. The C-Ray Cottage is the former working office of C. Ray Jes
Hot HOT 29
The C-Ray Cottage
House
$150 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
“Rainbows and Mermaids are proof that imagination and beauty go hand in hand.”Welcome to The Mermaid Lounge on Chincoteague Island. An absolutely adorable and affordable Beach getaway tucked on the ever-popular East Side - close to everywhere you want to be!If you’re not familiar with the East Side, imagine driving down a quiet road that hugs the s
Hot HOT 11
The Mermaid Lounge
Town House
$99 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
“Life is a journey that is not measured in miles or years, but in Experiences.” ~ Jimmy BuffettClose your eyes and feel the salty, sweet bay breeze wash over you. Breathe in the smell of Coppertone - hear the Gulls cry above. This is the very essence of Lammers Largo in beautiful Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on
Hot HOT 13
Lammers Largo
House
$195 - $550 / per night
Bedrooms 4 bedrooms
Bathrooms 3 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 13
Assateague Inn 205-S
Condominium
$45 - $355 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Island Sunset - “Every Sunset brings the promise of a new dawn.” ~ Ralph Waldo EmersonAnd we cannot think of a better place to begin this new dawn than at Newly Renovated ‘Island Sunset’ on beautiful Chincoteague Island. This one-of-a-kind home not only sits on South Main Street - home of THE most spectacular Sunsets - it features a Private Pier an
Hot HOT 14
Island Sunset
House
$125 - $495 / 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 13
East Side Breezes
House
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Fabulous Updates for 2022!!"We cannot control the wind, but we can direct the sail" - Life is busy. It gets more and more difficult to find that cherished time with family and friends. This is the sole purpose of Smooth Sailing on Chincoteague Island. It is a retreat. A destination. A place to rejuvenate and reconnect with those who matter the most
Hot HOT 13
Smooth Sailing
House
$135 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Carriage House - Relax, Rejuvenate, and Reconnect……The best things in Life are the people you love, the places you go, and the Memories you make! If you’ve been looking for that special place to make incredible Vacation Memories, you’re going to fall in love with beautiful Carriage House in Oyster Bay II! AND, your family dog (2 max) is welcome wit
Hot HOT 23
Carriage House
House Pet Friendly
$195 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 12 guests
Looking for a different kind of Beach Vacation? Dad likes to Golf, Mom and the kids want the Beach, and you don't want to leave Fido behind? How do you please everyone, you ask? We’ve got the answer right here at Salty Paws in beautiful Captain’s Cove Golf and Yacht Club!One of the Best Kept Secrets on the Eastern Shore of Virginia, Captain’s Cove
Hot HOT 16
Salty Paws
House Pet Friendly
$125 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Life is good, but Island Life is better!Looking for a Beach Break that will take your breath away, yet not break the bank? Welcome to The Teague House on peaceful and serene Marsh Island! This Newly Renovated Townhome in Captain’s Quarters Townhomes has it all, and is just a stone’s throw from our beautiful Little Island by the Sea!As you take the
Hot HOT 28
The Teague House
Town House
$85 - $350 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
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 14
Assateague Inn 208-S
Condominium
$45 - $363 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

Tell us what you're looking for and someone will contact you with available options.

I agree