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 175 properties available
Beach More, Worry Less…..If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New Addition to our Seaside Family has it all - that quintessential Chincoteague Charm you love, the Modern Amenities you want and need, and a fabulous Mid-Island Location - close to everywhere you want to be!Shore to Please is tucked on
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House Pet Friendly
$100 - $350 / per night
Bedrooms 5 bedrooms
Bathrooms 1 bath
Guests 10 guests
**Teague Time has a Brand New Fenced Yard for your Furbaby!**The best things in Life are the people we love, the places we've been, and the Memories we've made along the way. Welcome to Teague Time on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This beyond-adorable Vacation Cotta
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Teague Time
House Pet Friendly
$85 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Albion and the best Chincoteague Island Vacation you have ever had! This phenomenal, one-of-a-kind dream home is located on Willow Street, right in the heart of the island, and near everywhere you want to be. Lush, tropical landscaping will welcome you as you pull into the custom circular driveway, with parking for 3 cars. This spectacul
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House
$126 - $500 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
The welcome mat is out at spectacular Ariel's Grotto -  only minutes from Assateague National Seashore, home of the Famous Wild Ponies! This 3 Bedroom/2.5 Bath Home is simply stunning. Located on a very quiet street mid-island, this awesome Chincoteague Vacation Home is sure to make all of your Vacation Dreams come true!As you enter this Coastal Ca
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Ariels Grotto
House
$115 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Bishop House - a wonderful family home rich in the history and traditions of our wonderful Little Island by the Sea! Tucked on a spacious corner lot on Church Street, Bishop House truly is close to everywhere you want to be, yet still feels a million miles away from the real world. From this home base, you’re only a few steps away from o
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House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
We are big believers that every Home has a story.......a story rich in happiness and sadness, struggles and successes - that creates its very essence. The C-Ray Cottage has a story you will love.......This adorable Bayfront Waterman's Cottage exudes that quintessential Chincoteague Charm. The C-Ray Cottage is the former working office of C. Ray Jes
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The C-Ray Cottage
House
$150 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
We travel not to escape Life, but for Life not to escape us…..When was the last time you slowed down - took time to watch the birds dance over the water, or just listen to the breeze rustle the trees? Life is crazy - we know! We’re rushing to work, the kids are rushing to school - and the family pup just wants to tag along for all of it. What you n
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House Pet Friendly
$125 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to A Seagull’s Perch - Sunset Bay 320 - where salt in the air brings peace to the soul….Ahhh, 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 ov
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Sunset Bay Villa 320 - A Seagull's Perch
Condominium
$125 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Life is good, but Island Life is better!Looking for a Beach Break that will take your breath away, yet not break the bank? Welcome to No Problem on peaceful and serene Marsh Island! This Newly Renovated Townhome in Captain’s Quarters Townhomes has it all, and is just a stone’s throw from our beautiful Little Island by the Sea!As you take the exit f
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Town House
$89 - $325 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Bella's Beach Retreat - Assateague Inn 211 -has had some great updates including new Flooring and a totally new bathroom including shower with grab bars, some new furnishings, and new art! 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 Isl
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Bella's Beach Retreat - Assateague Inn 211
Condominium
$45 - $250 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
The best things in life are the people you love, the places you go, and the memories you make along the way…..Welcome to Misty Moon on beautiful Chincoteague Island - or as we like to call it, our Little Island by the Sea. Y’all, just wait until you see this adorable home, which has been lovingly restored and gorgeously decorated! Tucked back on a
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Misty Moon
House
$99 - $325 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Step into Lavinder House, a charming Victorian waterfront retreat on North Main Street in the heart of Chincoteague Island—where coastal calm meets storybook character. If you like unique historic homes that tell a story, this is the place for you! Local lore (and long-time island history) connects Lavinder House to actress Linda Lavin, of the hit
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Lavinder House
House
$250 - $725 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 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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