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 211 properties available
Calm Tide – Waterfront Serenity on Chincoteague Island!Welcome to Calm Tide, a peaceful waterfront escape on beautiful Chincoteague Island. Tucked on South Main Street, this charming townhome offers the perfect blend of privacy and scenery, with only one neighboring home and a shared pier that invites you to slow down and soak it all in.Wake to bre
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Town House
$165 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
May you always have a shell in your pocket, and sand in your shoes…..Sandy Bottoms - the name alone stirs up fond memories of family vacations from long ago. This wonderful 4 Bedroom home is ready to make your Vacation Dreams come true!With Classic Coastal Cape good looks, Sandy Bottoms is in the heart of the Island on Ridge Road - close to everywh
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Sandy Bottoms
House
$128 - $424 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 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
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House Pet Friendly
$175 - $800 / per night
Bedrooms 5 bedrooms
Bathrooms 2 baths
Guests 11 guests
There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the whole 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 Island to make Memories that you'll treasure forever
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Island Haven
Town House
$120 - $399 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Life’s a Beach - If you’re not barefoot, you’re overdressed….When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for just the right place - or just the right Experience, we should say - boy, do we have the place for you! K and S Paradise is nestled right in the heart of Chincoteague Islan
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House Pet Friendly
$106 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Meet Sunny Side Up - your bright and breezy Chincoteague Escape where every day starts on the sunny side! Tucked on Bunting Road, in the very heart of our Little Island by the Sea, this adorable end-unit townhome is equal parts cozy retreat and coastal adventure basecamp! Whether you’re sipping coffee on the porch, biking to see our famous Wild Pon
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Town House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
There’s a story behind every home—and “Your Song” tells a beautiful one. This Waterfront gem was named by the owner in memory of his late wife and her favorite song. Today, it welcomes guests with the same spirit of love, tranquility, and timeless beauty that inspired its name.Tucked on a quiet Canal in Captain’s Cove Golf and Yacht Club, you’ll ta
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House
$160 - $532 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Casa Del Canal - Captivating. Canalfront. Calling your name.....Looking for the perfect Eastern Shore Vacation Destination? Look no further than Casa Del Canal in gorgeous Captain's Cove - one of the best kept secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom/2 Bath Waterfront Home has something for everyone in the family. Located C
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House
$140 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 Bay Breeze in fabulous Captain’s Cove Golf and Ya
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House Pet Friendly
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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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Town House
$125 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Sky above, Sand below, Peace within….Life is short - and busy - OH, so busy. When was the last time you grabbed those who matter most and left it all behind, even if just for a few days?! If you’ve been longing for a Beach Break, we’ve got the perfect place for you, right here in the very heart of Chincoteague Island! Welcome to The Virginia Lee -
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The Virginia Lee
House
$99 - $345 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 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
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Sunset Bay Villa 110 - Hawk's Nest
Condominium Pet Friendly
$150 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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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