Chincoteague Waterfront Rentals

There’s nothing like being directly on the water! Select from our many waterfront vacation rentals on Chincoteague Island. Enjoy boating, fishing, crabbing, clamming, or just relaxing by the water.
Browse through our Waterfront House Rentals or Waterfront Condo Rentals.
Looking something a little different? Check out all of our Chincoteague Island vacation rentals for a complete selection.
109 properties available
Welcome to Ducks, Docks, and Flip Flops - what more could you want, right? This recently renovated and beyond adorable Waterfront Townhome is located on Marsh Island, directly across the Channel from Chincoteague Island. Offering amazing Channel Views and a Community Dock, it is the perfect Vacation Destination for a couples getaway or small family
Ducks, Docks, and Flip Flops
Town House
$89 - $325 / per night
2
bedrooms
1
bath
4
guests
Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the Refuge. Once you visit our beautiful Island, it stays with you forever. But life is so busy - it's hard to get away for a whole week every year, isn't it? Or maybe you're one who prefers to take many shorter trips over the course
Assateague Inn 207-S
Condominium
$45 - $220 / per night
1
bedroom
1
bath
4
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
Off the Record
House
$135 - $375 / per night
3
bedrooms
2
baths
6
guests
Stop for a moment and imagine your dream vacation - what would it be like? A spectacular Custom Home perched on the Assateague Channel with breathtaking Views? Or maybe a Dream Home in which everyone has a Master Bedroom with Waterfront Balcony and Private Master Bath? How about a warm and inviting Great Room where you can gather with those who mat
Stoney Point
House
$600 - $900 / per night
4
bedrooms
4
baths
8
guests
The tans may fade, but the Memories will last forever….Today’s world is so busy - meetings, soccer games, work, school, and repeat. When was the last time you grabbed those who matter most, and escaped the daily grind, just to BE together? Gaze at the water, take in the salty, sweet sea breeze - laugh, play, and tell stories - make precious Memorie
Shimmering Shores
House
$325 - $675 / per night
3
bedrooms
2
baths
7
guests
Sunset Bay 110 - Relax, Rejuvenate, Reconnect....Sunset Bay 110 is now DOG FRIENDLY with no additional pet fee! Must be pre-approved and max of 2.Welcome to Sunset Bay 110 - Hawk’s Nest - at fabulous Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge, a
Sunset Bay Villa 110 - Hawk's Nest
Condominium
$150 - $430 / per night
3
bedrooms
2
baths
8
guests
Sunset Bay 307 - Sometimes you just have to go with the Waves…..Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! 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 an
Sunset Bay Villa 307 - Picasso
Condominium
$125 - $336 / per night
3
bedrooms
2
baths
6
guests
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 is on the 1st Floor, and 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, a
The Pearl at Marsh Island
Condominium
$75 - $163 / per night
1
bedroom
1
bath
4
guests
Welcome to Assateague Inn 107 in the heart of Chincoteague Island at the The Assteague Inn. The Inn is a long time favorite of Beach Lovers, and sits less than 5 minutes from Assateague National Seashore, where our Wild Ponies roam free!What makes Assateague Inn 107 different from the other Suites at this beloved building? It’s the ONLY Suite that
Assateague Inn 107-A
Condominium
$60 - $266 / per night
1
bedroom
1
bath
4
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
Island Sunset
House
$125 - $459 / per night
3
bedrooms
2
baths
8
guests
Octopus’s Garden - “I’d like to be under the Sea ~ in an Octopus’s Garden in the shade!”When was the last time your Vacation took your breath away? If that is what you’ve been yearning for, clear your schedule - Paradise awaits you in beautiful Captain’s Cove Golf and Yacht Club! Octopus’s Garden is almost brand new, and beyond stunning. Tucked Can
Octopus's Garden
House
$125 - $383 / per night
4
bedrooms
3
baths
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
Calypso
House
$150 - $321 / per night
4
bedrooms
3
baths
8
guests
Tell us what you're looking for and someone will contact you with available options.
Copyright © 2026 • Seaside Vacations & Sales
All Rights Reserved.
