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 175 properties available
Oyster Bay Hideaway - Beach Days are the Best Days…..Just imagine relaxing on the Deck taking in that salty, sweet bay breeze - listening to the Tree Frogs sing - and watching Herons, Eagles, and Egrets fish for their morning meal in Eel Creek just behind the house…..This is living the shore life at Oyster Bay Hideaway on beautiful Chincoteague Isl
Hot HOT 32
Oyster Bay Hideaway
Town House Pet Friendly
$85 - $300 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
‘Off the Record’, we have to tell you - you are in for quite a treat!Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous ‘Off the Record’ 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 ha
Hot HOT 32
Off the Record
House Pet Friendly
$135 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!The most treasured heirlooms are the sweet memories of Family......Blue Heron is located in Eagle's Sound Estates, only 10 minutes from wonderful Chincoteague Island, Home of the Famous Wild Ponies and Misty of Chincoteague, yet you will feel as if you are in your own private Paradise. T
Hot HOT 33
Blue Heron
House
$175 - $300 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
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 crabbing or fishing from the Community Dock - or w
Hot HOT 35
Sunset Bay Villa 216
Condominium
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
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 20
Assateague Inn 103-S
Condominium
$45 - $358 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
**Captain's Rest is now Flex-Stay ALL year long!**We travel not to escape Life, but so that Life doesn't escape us. It's so hard to find time to break away from the daily grind and spend time with those who matter most - but, we all know there's nothing more important. Make time to make Memories, because we've got the place for you! Welcome to Capt
Hot HOT 16
Captains Rest
Town House
$99 - $575 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 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
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Hudson House
House
$150 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 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
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Painted Pony Cottage
House Pet Friendly
$75 - $224 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
Ready to kick back and enjoy a little “island time”? ‘Shore Beats Work’! If you’re looking for the perfect Home Base for your next Chincoteague Island Adventure, look no further than ‘Shore Beats Work’ in Eastwinds. Located in the very heart of Chincoteague Island, this lovely Townhome is convenient to everywhere you want to be on our beautiful Isl
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Shore Beats Work
Town House
$80 - $285 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 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 13
Salty Paws
House Pet Friendly
$125 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Our Memories of the Ocean live on, long after our footprints are gone….Making Memories - isn’t that what it’s all about? Escaping from the daily grind, and reconnecting with those who matter most. Kids grow up fast, and life is so short - the Beach is calling - and we have the perfect homebase for your next Chincoteague Island adventure….Welcome to
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Misty Breeze
Town House
$88 - $782 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 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 30
Island Sunset
House
$125 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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