Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

Browse over 150 Chincoteague Island Rentals, all at the Best Rates

Welcome to beautiful Chincoteague Island, also known as Our Little Island by the Sea! 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 182 properties available
Stunning Updates!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
Hot HOT 19
Assateague Inn 111-2R
Condominium
$45 - $301 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague Lovers for years. Located less than 5 minutes from Assateague National Seashore, and allowing short stays all year long, it’s the perfect Vacation getaway for singles, couples, or small families. Assateague Inn 100-2R is actually
Hot HOT 22
Assateague Inn 100-2R
Condominium
$45 - $336 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
We travel not to escape Life, but for Life not to escape us…..When was the last time you slowed down - took time to watch the birds dance over the water, or just listen to the breeze rustle the trees? Life is crazy - we know! We’re rushing to work, the kids are rushing to school - and the family pup just wants to tag along for all of it. What you n
Hot HOT 28
The Mane Escape
House Pet Friendly
$125 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
High Tides and Good Vibes…..Welcome to Tranquil Tides Retreat - a newly renovated and beyond adorable Waterfront Townhome located on Marsh Island, directly across the Channel from Chincoteague Island. Perfect for a small family or a couples getaway, you can take that beach break you’ve been longing for - without breaking the bank!As you take the ex
Hot HOT 34
Tranquil Tides Retreat
Town House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Welcome to Assateague Inn 107 in the heart of Chincoteague Island at the The Assteague Inn. The Inn is a long time favorite of Beach Lovers, and sits less than 5 minutes from Assateague National Seashore, where our Wild Ponies roam free!What makes Assateague Inn 107 different from the other Suites at this beloved building? It’s the ONLY Suite that
Hot HOT 28
Assateague Inn 107-A
Condominium
$65 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 42
The C-Ray Cottage
House
$150 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 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 NO ADDITIONAL FEE!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 per
Hot HOT 16
Wind Rose
House Pet Friendly
$100 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 7 guests
Welcome to Casa Del Sol - “Live in the Sunshine, swim the Sea, drink the Wild Air….”When was the last time your Vacation took your breath away? If that is what you’ve been yearning for, clear your schedule - Paradise awaits you in beautiful Captain’s Cove Golf and Yacht Club!Casa Del Sol is Brand New Construction in 2024, and beyond stunning. Tucke
Hot HOT 13
Casa Del Sol
House
$200 - $625 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sitting Waterfront on Eel Creek, you'll enjoy lovely Views!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
Hot HOT 11
Assateague Inn 213-2R
Condominium
$45 - $248 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 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 26
Catch of the Day
Town House
$110 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous Pier Pressure in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom Waterfront Dream Home has something for everyone in the family. Located at the water’s edge dir
Hot HOT 16
Pier Pressure
House
$125 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Lily Pad has had some BIG updates including a Fenced In Back Yard for your furbabies, New Flooring in the Kitchen, New Furnishings, New Washer and Dryer, the addition of a Dishwasher!Lily Pad on beautiful Chincoteague Island is the perfect place to make your Vacation Dreams come true. This adorable and affordable Vacation Home is located on the eve
Hot HOT 26
Lily Pad
House Pet Friendly
$85 - $274 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests

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