Chincoteague Island Vacation Rentals

Chincoteague Island vacation rental homes on Virginia’s Eastern Shore — Seaside Vacations & Sales

Welcome to beautiful Chincoteague Island! Are you ready for a vacation away from the big city and crowded beach resorts? Search through over 170 Chincoteague Island vacation rentals that offer no high-rises, boardwalks, or traffic jams to interfere with your relaxation. For over 15 years, Seaside Vacations & Sales has offered beautiful house rentals and condo rentals that fit any family size or group gathering, all at the lowest rates on the island.

Seaside Vacations offers a variety of options for your upcoming stay, so you never have to settle. Select from waterfront rentals, rentals with pools, and pet-friendly rentals—because even your furry family members deserve a vacation. We also offer rentals in popular communities like Captain's Cove Golf & Yacht Club, Marsh Island, Piney Island, Pointer Lane, Sunset Bay Villas, and The Assateague Inn.

Come experience the charm and natural beauty of Chincoteague Island, including beloved traditions like the world-famous Pony Swim.

Properties Available 210 properties available
“Travel not to escape Life, but so Life doesn't escape you.” ~ UnknownWelcome to The Feathered Nest - a tranquil retreat in the very heart of Chincoteague Island. This spectacular home is Brand New Construction in 2025, and will absolutely make your jaw drop! Tucked on a super quiet Lane off the beaten path, you’ll feel a million miles away from th
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The Feathered Nest
House
$175 - $547 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
"Temenos is a Greek word used to designate a special place - a place of unique beauty - where you can go to separate yourself, to serve as a Retreat, a place for quiet Reflection, a place to recover your sacred center when the world is overwhelming." These words from the thoughtful Owners of this beautiful Home say it all - and encompass what we fe
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Island Temenos
House
$90 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 1 bath
Guests 8 guests
Kick back and soak up the good vibes at Sundance! This bright and breezy getaway is made for sun seekers, beach lovers, and anyone ready to unwind in pure comfort and style here on Chincoteague Island! Less than 10 minutes from Chincoteague National Wildlife Refuge and Assateague National Seashore - where our Famous Wild Ponies roam free - it’s the
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Sundance
House
$125 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Deja Blue - there is no color quite like this…..You know that feeling when you see the Ocean and all your worries just wash away? That’s the feeling you get as soon as you walk through the French Doors at Deja Blue on Chincoteague Island. This adorable Cottage oozes that quintessential Chincoteague Charm you love, plus has the Modern Amenities you
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Deja Blue
House
$90 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
“Time has a wonderful way of showing us what really matters…..” ~ UnknownTime flies, as they say - you blink and the kids are off to college. This is why it’s so important to make time to just BE together now - to break away from the day to day and play together, laugh together, make unbelievable memories that will last a lifetime. Welcome to Cedar
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Cedar Haven
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Cedar Haven
House
$99 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Looking for a different kind of Beach Vacation? Dad likes to Golf, Mom and the kids want the Beach, and you need a little space for the whole gang - how do you please everyone, you ask? We’ve got the answer right here at Fairway Stay in beautiful Captain’s Cove Golf and Yacht Club!One of the Best Kept Secrets on the Eastern Shore of Virginia, Capta
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Fairway Stay
House
$125 - $300 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Everyday should be a Beach Day…..When was the last time you had a Vacation that truly took your breath away? Life is so busy - work, school, non-stop commitments, or so it seems. If you’ve been yearning for a getaway that will relax, refresh, and rejuvenate you, clear the calendar, because we have the perfect place for you!Welcome to Duck Harbor at
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Duck Harbor at Waters Edge
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Duck Harbor at Waters Edge
Town House
$125 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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
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Shimmering Shores
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Shimmering Shores
House
$325 - $675 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Live your Life by a compass, not a clock….Work, school, traffic, homework, repeat - right?! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Breathe - you’re on Island Time now. And boy, do we hav
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Happy Hideaway
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Happy Hideaway
House
$85 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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
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The Baywatch Bungalow
House Pet Friendly
$125 - $295 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Of all the paths you take in life, make sure a few of them are sandy…..Welcome to ‘Paradise’ on dreamy Chincoteague Island - it’s not just a vacation home, it’s a feeling - relax, rejuvenate, and reconnect with those who matter most at this gorgeous Waterfront Townhome nestled directly on the Chincoteague Bay.Tucked away in the perfect location on
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Paradise
Town House
$145 - $520 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Island days, Island ways, surf, sun, and happy days…..We believe that finding the “perfect” Vacation Home is so much more than merely finding a place to lay your head at night. We are all about “Experiences” ~ and a stay at Nunzs Cove is just that ~ a blissful Experience that will be treasured by your family for years to come.As you pull down the
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Nunzs Cove
House
$175 - $425 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 7 guests

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Frequently Asked Questions about Chincoteague Island

What is Chincoteague Island known for?

Chincoteague Island is Virginia's only resort island, famous for its wild Chincoteague ponies, the annual Pony Swim, and its gateway access to the Chincoteague National Wildlife Refuge on Assateague Island.

Where is Chincoteague Island located?

Chincoteague Island is located on Virginia's Eastern Shore, easily accessible from major Mid-Atlantic cities. It sits approximately 3.5 hours from Washington D.C., 3 hours from Philadelphia, and 2 hours from Richmond. The island is connected to the mainland by a causeway on Route 175.

When is the best time to visit Chincoteague Island?

Peak season runs from Memorial Day through Labor Day, when warm weather, beach access, and full island activities are available. Spring (March–May) and fall (September–October) offer smaller crowds, lower rental rates, and excellent wildlife viewing. The famous Chincoteague Pony Swim takes place annually on the last Wednesday and Thursday of July — one of the most popular events of the year.

Can I see the wild ponies on Chincoteague Island?

Absolutely — the wild Chincoteague ponies are one of the island's most beloved attractions. They roam freely on Assateague Island within the National Wildlife Refuge, and visitors can spot them along the Wildlife Loop, from boat tours, and during the world-famous Pony Swim each July. The refuge recommends staying at least 40 feet from the ponies at all times.

Is there a fee to access Chincoteague National Wildlife Refuge?

Yes, there is a day use fee to enter the Wildlife Refuge and access the beach at Assateague Island National Seashore.

Are there pet-friendly vacation rentals on Chincoteague Island?

Yes — Seaside Vacations offers a selection of pet-friendly Chincoteague rentals for guests who want to bring their four-legged family members along. Browse our pet-friendly rentals to find the perfect fit for your group.

Is the beach at Assateague Island still open in 2026?

Yes — the recreational beach at Chincoteague National Wildlife Refuge remains open throughout the 2026 season.

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