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 174 properties available
Sunny Shack - The Best Days are Beach Days..…..Welcome to Sunny Shack on wild and wonderful Chincoteague Island! This stunning Waterfront Dream Home is brand new to the Seaside Vacations’ Family, but has been a fan-favorite Vacation Rental for years!Ahhhh, South Main Street - if you aren’t familiar, South Main is home to some of THE most amazing Su
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Town House
$145 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Lighthouse Overlook - Every day should be a Beach Day…..Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Lighthouse Overlook was made
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House
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Looking for somewhere truly special to spend your Chincoteague Island Family Vacation this year? Look no further, as special doesn't even begin to describe the tranquility and beauty of waterfront Family Tides. This adorable home is located directly on Lewis Creek's deep water, so by all means, bring the boat, kayaks, jet skis, or water toy of choi
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House
$135 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Pony Swim Crossing - Chincoteague Island is calling…..“To sit in silence at the shore, watch the waves and hear the surf, is to appreciate the very breath and heartbeat of the earth.” ~ UnknownIsn’t it time to break away from the daily grind? The stress, the traffic, and oh, “schedules” - aren’t we all just a little too “scheduled” in life? Grab th
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Town House
$99 - $450 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 5 guests
Sunset Breeze - if you’re not wearing flip flops, you’re overdressed…..At the Beach, Life is different - Time doesn’t move hour to hour, but mood to moment. We live by the currents, plan by the tides, and follow the sun til it sets…..And there is no better place to do this than at beautiful Sunset Breeze right here on Chincoteague Island! Sitting W
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House
$125 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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
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Condominium
$65 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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
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Town House
$89 - $325 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
“Live in the sunshine, swim in the sea, drink the wild air.” ~ Ralph Waldo EmersonThere’s something about a day at the Beach - the warm sun on your face, the salty, sweet sea breeze, the sound of the Laughing Gulls - not to mention our Famous Wild Ponies - pure heaven! When was the last time you escaped the day to day, just to relax, rejuvenate, an
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House
$165 - $575 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Channel View Charmer - Every moment has the potential to be amazing….**Now Dog Friendly!** Channel View Charmer is totally Renovated for 2023 - you're going to love it!Looking for the perfect beach getaway for your family? Channel View Charmer will charm it’s way into your heart forever! This adorable Water View Home has to be in one of the best lo
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House Pet Friendly
$90 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 8 guests
Expanded Deck and Boardwalk!You know that favorite song that just stays with you - the one you long to hear again and again? This is the feeling you will get while staying at Rhythm and Blues on beautiful Chincoteague Island. Tucked away on the East Side, this Charming Chalet will steal your heart. Located only steps from the Public Boat Launch and
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House
$105 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 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
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House
$600 - $900 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Memories at the Beach last a lifetime…..Hoping to land the big one this year for your Chincoteague Island Vacation? Look no further than adorable “Catch of the Day” on super quiet and peaceful Tim Lane, just off Deep Hole Road, in the very heart of Chincoteague Island!This delightful Duplex sits tucked at the end of the Lane, surrounded by peaceful
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Town House
$110 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 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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