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
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
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Assateague Inn 207-S
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Assateague Inn 207-S
Condominium
$45 - $308 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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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Shore to Please
House Pet Friendly
$95 - $350 / per night
Bedrooms 5 bedrooms
Bathrooms 1 bath
Guests 10 guests
‘By the Bay’ - Is there anywhere you’d rather be?!Welcome to beautiful 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 over the water. Try your hand at
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Sunset Bay Villa 313 - By the Bay
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Sunset Bay Villa 313 - By the Bay
Condominium
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Mariner’s Light - a lovingly restored historic home that blends timeless Chincoteague charm with fresh, shabby-chic coastal style. Thoughtfully renovated from top to bottom, this adorable vacation retreat feels both nostalgic and beautifully new—where original character meets breezy modern comfort. Y’all are going to absolutely love this
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Mariner's Light
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Mariner's Light
House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 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
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Teague Time
House Pet Friendly
$85 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Saltwater Pony - Beach Mode activated!Have you been longing for a Beach Vacation that is truly easy-breezy? Clear your calendar and grab those who matter most, because we’ve got you covered with this gorgeous Custom Home in the very heart of Chincoteague Island! Saltwater Pony is tucked on Ridge Road - close to everywhere you want to be
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Saltwater Pony
House
$125 - $415 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 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
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Assateague Inn 205-S
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Assateague Inn 205-S 3
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Assateague Inn 205-S
Condominium
$45 - $308 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Welcome to beautiful 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 over the water. Try your hand at crabbing or fishing from the Community Dock - or w
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Sunset Bay Villa 209
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Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Mainstay on Chincoteague Island! True to its name, Mainstay is your steady anchor on Chincoteague Island—an inviting coastal retreat where comfort, calm, and island living come together, oh, so beautifully. This incredibly special home is tucked on North Main, just a hop, skip, and jump away from Assateague National Seashore, where our f
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Mainstay
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Mainstay
House
$200 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Were you dazzled by your last Vacation? If not, you clearly were not staying at breathtaking Paradise View in Richardson’s Landing! Tucked on a quiet cul-de-sac directly on the water’s edge, Paradise View isn’t simply a place to lay your head at night, it’s a true Vacation Experience - and one you will treasure forever!As you pull down the lane, Pa
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Paradise View
House
$375 - $700 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is
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Pony Paradise
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Pony Paradise
House Pet Friendly
$125 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Have you always wanted to vacation on Chincoteague Island, but couldn't bear the thought of 6 of you in a hotel room? Love the idea of a Vacation Home, but don't want to break the bank? Look no further than Newly Renovated ‘Beachy Place’ at Sea Tag Lodge, sitting directly on the Assateague Channel! The Sea Tag Lodge has been helping families make a
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Beachy Place
Condominium
$85 - $325 / per night
Bedrooms 2 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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