10% Off Memorial Weekend Special

Stay in Chincoteague Island for 3+ nights and get 10% OFF your rental rate now thru June 9th. That means 10% more Fun, 10% more Memories, and 10% more in your pocket. Book your 3+ night stay today!


You MUST use the Promo code, memorialday23, in order to receive this discount.

Call us at (844) 662.2583 if you need any assistance.


Properties Available 42 properties available
Calypso - Dance to the Song of the Sea.....You know that feeling you get while relaxing on the beach and listening to steel drums play while the Sea Breeze blows through your hair? Enjoy this feeling every day at fabulous Calypso in Captain's Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 4 B
Hot HOT 10
Calypso
House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Traveling - it leaves you speechless, then turns you into a storyteller…..And oh, the stories that newly renovated ‘Lookout on Main’ has in store for you! This one-of-a-kind Dream Home is located on South Main Street, directly facing THE most amazing Chincoteague Sunsets you could imagine. And you want waterfront, you say? It doesn’t get much more
Hot HOT 31
Lookout on Main
House
$250 - $885 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Of all the paths you take in life, make sure a few of them are sandy…..Welcome to ‘Paradise’ on dreamy Chincoteague Island - it’s not just a vacation home, it’s a feeling - relax, rejuvenate, and reconnect with those who matter most at this gorgeous Waterfront Townhome nestled directly on the Chincoteague Bay.Tucked away in the perfect location on
Hot HOT 16
Paradise
Town House
$145 - $549 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
The Baywatch Bungalow - If you’re not barefoot, then you’re overdressed…..Close 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 The Baywatch Bungalow in beautiful Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern S
Hot HOT 8
The Baywatch Bungalow
House Pet Friendly
$125 - $295 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Peace. Love. Beach.Have you been yearning for a break from the hectic day to day? An affordable getaway that will bring those together who matter most - and without breaking the bank? We’ve got you covered - take a look at One Peace Cottage on beautiful Chincoteague Island - where our Wild Ponies roam free, and there’s not a high-rise building to b
Hot HOT 14
One Peace Cottage
House
$85 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 14
Off the Record
House Pet Friendly
$135 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our little piece of Paradise - the Wild Ponies running free, Saltwater Cowboys leading the way, the Saltiest, Sweetest Oysters to be found, and hands down THE best Sunsets over the water. Guess what? It's ALL true - isn't it time you di
Hot HOT 31
Saltwater Cottage
House Pet Friendly
$85 - $275 / 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 - $295 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 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 17
Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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
Hot HOT 32
Painted Pony Cottage
House Pet Friendly
$75 - $224 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
Expanded Deck and Boardwalk!You know that favorite song that just stays with you - the one you long to hear again and again? This is the feeling you will get while staying at Rhythm and Blues on beautiful Chincoteague Island. Tucked away on the East Side, this Charming Chalet will steal your heart. Located only steps from the Public Boat Launch and
Hot HOT 33
Rhythm & Blues
House
$105 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Casa Del Canal - Captivating. Canalfront. Calling your name.....Looking for the perfect Eastern Shore Vacation Destination? Look no further than Casa Del Canal in gorgeous Captain's Cove - one of the best kept secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom/2 Bath Waterfront Home has something for everyone in the family. Located C
Hot HOT 5
Casa Del Canal
House
$140 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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

I agree