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 176 properties available
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
Carriage House - Relax, Rejuvenate, and Reconnect……The best things in Life are the people you love, the places you go, and the Memories you make! If you’ve been looking for that special place to make incredible Vacation Memories, you’re going to fall in love with beautiful Carriage House in Oyster Bay II! AND, your family dog is welcome with no add
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Carriage House
House Pet Friendly
$195 - $575 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 12 guests
Welcome to Go with the Flow — your laid-back waterfront escape on Marsh Island, just across the channel from Chincoteague Island. Here, days move at the pace of the tide, with salty breezes, glowing sunsets, and front-row seats to island life. Whether you’re sipping coffee on the deck or watching boats drift by, this is a place where you can truly
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Go with the Flow
Town House
$89 - $325 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Beachgrass Bungalow - High Tides and Good Vibes….The best things in Life are the people we love, the places we’ve been, and the memories we make along the way…..Life is busy - plain and simple. Work, meetings, schedules, lessons - pretty much chaos - all the time! This makes breaking away from the day to day more important than ever. Pack a bag, gr
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Beachgrass Bungalow
House Pet Friendly
$99 - $325 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, you'll be tucked away in a quiet location in the heart of our Island, yet close to everywhere you want to be. The Attractions of Historic Main Street with so many quaint Shops and Restaurants, Robert Reed Waterfront Park, and the
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Breezy Corner
House
$90 - $285 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 7 guests
The Teal on Eel Creek - Beach Days are the Best Days…..Just imagine relaxing on the Deck taking in that salty, sweet bay breeze - listening to the Tree Frogs sing - and watching Herons, Eagles, and Egrets fish for their morning meal in Eel Creek just behind the house…..This is living the shore life at The Teal on Eel (formerly Oyster Bay Hideaway)
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The Teal on Eel Creek
Town House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
New Screened Porch, Expanded Sunroom, New Front Deck, and Electric Vehicle Charger! "Les Bon Temps" loosely translates to "Let the good times roll" - can you think of a better phrase to kick off your Chincoteague Island Vacation this year? Tucked away on the East Side, this quintessential Chincoteague Cottage is beyond charming.  Located only steps
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Les Bon Temps
House
$55 - $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
$195 - $675 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Give me the Sea, and a little Cottage just to be…..Welcome to ‘Making Memories on Mumford’ - an adorable new addition to our Seaside Vacations’ Family! This cozy home is not just a place to lay your head each night - it’s like a visit with old friends - so warm, welcoming, and comfortable. Tucked in the heart of our Little Island by the Sea, you’ll
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Making Memories on Mumford
House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the 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 I
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The Happy Crab
Town House
$120 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Traveling - it leaves you speechless, then turns you into a storyteller…..And oh, the stories that newly renovated ‘Lookout on Main’ has in store for you! This one-of-a-kind Dream Home is located on South Main Street, directly facing THE most amazing Chincoteague Sunsets you could imagine. And you want waterfront, you say? It doesn’t get much more
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Lookout on Main
House
$250 - $885 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Assateague Inn 102 has been completely renovated for 2025, and is beachy and beautiful - check it out!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
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Assateague Inn 102-S
Condominium
$85 - $275 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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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