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
Beachgrass Bungalow - High Tides and Good Vibes….The best things in Life are the people we love, the places we’ve been, and the memories we make along the way…..Life is busy - plain and simple. Work, meetings, schedules, lessons - pretty much chaos - all the time! This makes breaking away from the day to day more important than ever. Pack a bag, gr
Hot HOT 29
Beachgrass Bungalow
House Pet Friendly
$99 - $285 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 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
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 23
Island Sunset
House
$125 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 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 15
Coves Point
House
$135 - $385 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 37
Lookout on Main
House
$132 - $885 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Have you ever asked yourself what the purpose of life is? Here at Seaside, we believe it’s all about spending time with those that matter most, and making memories you’ll cherish forever. And if you can make the time, we’ve got the most amazing home to tell you about…..Welcome to The Porpoise of Life in the very heart of Chincoteague Island. This
Hot HOT 31
The Porpoise of Life
House
$150 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Coastal Crab in Captain’s Cove - Just another day in Paradise…..There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at beautiful Coastal Crab in Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly on the C
Hot HOT 24
Coastal Crab
House
$125 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 24
Waterfront Wonder
House Pet Friendly
$112 - $535 / 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….There’s nothing like the smell of salt in the air and a warm breeze through your hair - the complete feeling of freedom that engulfs you the moment you know your Vacation is about to begin. And that’s what you’ll find at Dockside Dreams in fabulous Captain’s Cove Golf a
Hot HOT 40
Dockside Dreams
House Pet Friendly
$115 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Bliss by the Bay - If you’re wearing flip flops, you’re overdressed!There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at Bliss by the Bay in beautiful Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly
Hot HOT 22
Bliss by the Bay
House
$125 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
GREAT UPDATES for 2024 ~ New Flooring, New Furnishings, and Updated Decor ~ New Pics coming soon!Live for the moments you can’t put into words…..When was the last time you took a Vacation that truly took your breath away? A Vacation Home shouldn’t be just a place to lay your head at night - it’s the heart of your Vacation - a place to relax, rewind
Hot HOT 41
Coastal Retreat
House Pet Friendly
$109 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 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 42
House on the Dune
House
$325 - $600 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests

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