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
Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Little Red Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Str
Hot HOT 21
Little Red Cottage
House
$100 - $275 / per night
Bedrooms 2 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 21
Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 ready to make your Vacation Dreams come true!With Classic Coastal Cape good looks, Sandy Bottoms is in the heart of the Island on Ridge Road - close to everywh
Hot HOT 8
Sandy Bottoms
House
$128 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 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 7
Georges Retreat
House
$75 - $219 / 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 16
The Baywatch Bungalow
House Pet Friendly
$125 - $295 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, you'll be tucked away in a quiet location in the heart of our Island, yet close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the
Hot HOT 13
Breezy Corner
House
$90 - $285 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 7 guests
Casa Playa - Peace, Love, and Sandy Feet……Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Casa Playa is all about - kicking back, tak
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Casa Playa
House
$100 - $275 / 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 21
Blue Heron
House
$175 - $325 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Sometimes you just have to go with the waves…..Looking to catch a beach getaway at a family-friendly price? Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day! This adorable 2 Bedroom/2 Full Bath home is located in the heart of our little Island - just a short stroll from Maddox Boulevard, Steamers, and The I
Hot HOT 13
Fishhook Hideaway
Town House
$75 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 11
Calypso
House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Cove’s Point - Of all the paths you take in life, make sure a few of them are sandy…….When was the last time you had a vacation that took your breath away? If this is what you’ve been craving, Cove’s Point is the place for you. Located in gorgeous Captain’s Cove Golf and Yacht Club - one of the best kept secrets on the Eastern Shore of Virginia, yo
Hot HOT 24
Coves Point
House
$150 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Give me the Sea and a little Cottage just to be….The first time we saw ‘Crepe Myrtle Cottage’, we felt an inviting warmth pulling us in. Very difficult to describe, it’s the feeling of true Southern Charm, mixed with the appeal of modern amenities and chic decor. To us, it is the absolutely perfect combination of the quintessential Chincoteague Cot
Hot HOT 23
Crepe Myrtle Cottage
House
$135 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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