Chincoteague Waterfront Rentals
Select from our many waterfront vacation rentals on Chincoteague Island and in Captains Cove. Enjoy boating, fishing, crabbing, clamming, or just relaxing by the water. The amenities that are included in your vacation rental will make your vacation not only the best vacation ever, but the most memorable one as well.
Browse through our Waterfront House Rentals, Waterfront Condo Rentals, Captain's Cove Golf & Yacht Club, or search all of our Chincoteague vacation rental here.
94 properties available
Welcome to The Pearl at Marsh Island - leave your troubles at the door, you won't be needing them here! This super charming and newly renovated 1 Bedroom/1 Bath Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel, the Causeway, and the Chincoteague Chann
The Pearl at Marsh Island
Condominium
$60 - $200 / per night
1
bedroom
1
bath
4
guests
Just give me the Sea, and a little Cottage just to be…..One of Chincoteague’s most beloved Vacation Homes, Shackeau East, is now part of our Seaside Vacations’ Family! Resting by the water’s edge in ever-popular Piney Island, this adorable Cottage has quite the following! Piney Island is the closest community to Assateague National Seashore, where
Shackeau East
Cottage
$105 - $325 / per night
1
bedroom
1
bath
4
guests
Island Days and Sunny Rays…..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, Marsh, 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 fi
Sunset Bay Villa 306 - Our Pleasure
Condominium
$125 - $525 / per night
3
bedrooms
2
baths
7
guests
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
Beachgrass Bungalow
House
$99 - $285 / per night
2
bedrooms
2
baths
6
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
Barefoot Breeze
House
$150 - $500 / per night
4
bedrooms
3
baths
8
guests
Serenity Now - It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by c
Serenity Now
House
$300 - $395 / per night
3
bedrooms
2
baths
6
guests
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague I
The Happy Crab
Town House
$120 - $395 / per night
3
bedrooms
2
baths
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
Waterfront Wonder
House
$112 - $535 / per night
3
bedrooms
2
baths
8
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
Sunset Bay Villa 220 - Vista Costiera
Condominium
$150 - $375 / per night
3
bedrooms
2
baths
8
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
The Porpoise of Life
House
$150 - $550 / per night
3
bedrooms
3
baths
6
guests
Wonderview 208 ~ Take the Journey to enjoy the View…..Life gets busy - work, kids, appointments, pets - it never seems to stop. This makes it more important than ever to take time to stop and smell the roses - or more appropriately, the salty, sweet sea breeze. If you can make the time, we most definitely have the place….Welcome to fabulous Wonderv
Wonderview 208
Condominium
$100 - $375 / per night
2
bedrooms
2
baths
4
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
Calypso
House
$150 - $375 / per night
4
bedrooms
3
baths
8
guests
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