Chincoteague Waterfront House Rentals

Wake up to the sun rising over the water with your own Chincoteague Waterfront Home Rental. Take a seat and soak in the water-views. Enjoy the comforts and peaceful surroundings of Chincoteague Island. Our Waterfront Rentals are located throughout Chincoteague Island, so no matter which home you select you will be close to the water and all attractions this island has to offer. We even offer Pet Friendly Waterfront Vacation Rentals so you can bring your furry family members with you. Everyone can enjoy Chincoteague Island.

Browse the selection below or check out all our Chincoteague Rentals here!


Properties Available 39 properties available
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 14
Island Sunset
House
$125 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Life is simple….just add water!The way we live today is crazy - we’re always in a hurry! Work, school, meetings, repeat. It’s so hard to find the time to gather those who mean the most to simply BE together. This is where “Dock Holiday” comes in - this home was made for making family memories together. This spectacular Waterfront Home is Brand New
Hot HOT 36
Dock Holiday
House
$145 - $550 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Sunsets are proof that no matter what happens, every day can end beautifully - and there is no better place to take in one of our famous Chincoteague Sunsets than fabulous Waterfront Wonder (formerly Sunset Foals). With gorgeous Newly Refinished, but still Historic, Hardwood Floors, and other upgrades, Waterfront Wonder still oozes the quintessenti
Hot HOT 17
Waterfront Wonder
House Pet Friendly
$112 - $535 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Collect Memories, not things…..Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chinco
Hot HOT 216
Teal Cottage
House
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Life’s at ease with an Ocean Breeze……You know that feeling you get when you step onto the Beach for the first time each Summer? That first deep breath - the saltiness of the Sea, the scent of Coppertone, the sound of the Gulls - this is life at Barefoot Breeze on Chincoteague Island. It’s not just a Vacation Rental, it’s a Destination, an Experienc
Hot HOT 21
Barefoot Breeze
House
$150 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Travel - It leaves you speechless, then turns you into a Storyteller…..When was the last time you took a Vacation that took your breath away? If you’ve been looking for that one-of-a-kind Vacation Experience, we’d love to introduce you to ‘House on the Dune’ in the prestigious Wildcat Community on Chincoteague Island. This stunning Custom Home is 1
Hot HOT 36
House on the Dune
House
$325 - $600 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 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 8
Calypso
House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Looking for the Modern Amenities you need, but still want the Character and Charm of a true Chincoteague Island Historic Home? Look no further than lovely Waterfront Angel's View - a heavenly home located on Main Street directly across from the Chincoteague Bay that offers you amenities, charm, water access and more! And new for 2021, Angel's View
Hot HOT 12
Angels View
House
$90 - $285 / per night
Bedrooms 3 bedrooms
Bathrooms 2 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 39
Lookout on Main
House
$139 - $885 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
New Stainless Appliances for 2023!Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When is the last time you broke away from the day-to-day with those you love? Well, the time is now, and the Vacation Home is magnificent Captain Freeland. This beautiful Canalfront Home is located in prestigi
Hot HOT 17
Captain Freeland
House
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Marsh Madness - Because saltwater is simply good for the soul…..**Marsh Madness now sleeps 12 and is Dog Friendly with a $100 Pet Fee per dog! AND, has a fully enclosed fence in the backyard!Break away from the daily grind at Marsh Madness - leave your troubles at the door, you won't be needing them here! This incredibly unique Waterfront Home trul
Hot HOT 62
Marsh Madness
House Pet Friendly
$175 - $700 / per night
Bedrooms 5 bedrooms
Bathrooms 2 baths
Guests 11 guests
Nothing soothes the soul like a day by the water…..If you love living at the water’s edge, we have the perfect Vacation Destination for you - with 360 degree gorgeous Water Views! Welcome to Anchors Away in Captain’s Cove Golf and Yacht Club! One of the Best Kept Secrets on the Eastern Shore of Virginia, Captain’s Cove is only 25 short minutes by c
Hot HOT 26
Anchors Away
House Pet Friendly
$44 - $800 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests

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