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 169 properties available
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 15
Assateague Inn 103-S
Condominium
$45 - $368 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sunset Bay 307 - Sometimes you just have to go with the Waves…..Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! 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 an
Hot HOT 26
Sunset Bay Villa 307 - Picasso
Condominium
$125 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Serenity Now -  It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by c
Hot HOT 21
Serenity Now
House
$250 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 16
Sandy Bottoms
House
$128 - $425 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 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 19
Eastwinds 18
Town House Pet Friendly
$70 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 113
Georges Retreat
House
$75 - $240 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 14
Sunrise Serenade
Condominium
$65 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
‘By the Bay’ - Is there anywhere you’d rather be?!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
Hot HOT 17
Sunset Bay Villa 313 - By the Bay
Condominium
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Waterfront Sunsets - Sunsets are proof that no matter what happens, every day can end beautifully…..This adorable Efficiency 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, the Causeway, and the Chincoteague Channel. Perfect for a Romanti
Hot HOT 24
Waterfront Sunsets
Condominium
$60 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 3 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 19
Smooth Sailing
House
$135 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Beachgrass Bungalow - High Tides and Good Vibes….The best things in Life are the people we love, the places we’ve been, and the memories we make along the way…..Life is busy - plain and simple. Work, meetings, schedules, lessons - pretty much chaos - all the time! This makes breaking away from the day to day more important than ever. Pack a bag, gr
Hot HOT 29
Beachgrass Bungalow
House Pet Friendly
$99 - $285 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
HUGE UPDATES for 2023 - it's gorgeous!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 ta
Hot HOT 14
Assateague Inn 105-S
Condominium
$45 - $367 / 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