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 217 properties available
‘Off the Record’, we have to tell you - you are in for quite a treat!Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous ‘Off the Record’ in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom Waterfront Dream Home ha
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House Pet Friendly
$135 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sitting Waterfront on Eel Creek, you'll enjoy lovely Views!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
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Assateague Inn 213-2R
Condominium
$45 - $247 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Life’s at ease with a bay breeze…..Do you yearn to be so close to the water that you can take in that salty, sweet sea breeze while you sleep? Imagine fishing and crabbing only steps from your house - or having your Boat docked just behind the house - all the joys of living at the Water’s Edge.Welcome to Water’s Edge in the heart of Chincoteague Is
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Town House
$100 - $350 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Assateague Inn 106 is newly renovated with New Flooring, Cabinets, Renovated Bathroom, and Fresh Paint - it's gorgeous!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
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Condominium
$45 - $247 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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
House
$275 - $675 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Just give me the Sea, and a little Cottage just to be…..One of Chincoteague’s most beloved Vacation Homes, Shackeau East, is now part of our Seaside Vacations’ Family! Resting by the water’s edge in ever-popular Piney Island, this adorable Cottage has quite the following! Piney Island is the closest community to Assateague National Seashore, where
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House
$125 - $325 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Lily Pad has had some BIG updates including a Fenced In Back Yard for your furbabies, New Flooring in the Kitchen, New Furnishings, New Washer and Dryer, the addition of a Dishwasher!Lily Pad on beautiful Chincoteague Island is the perfect place to make your Vacation Dreams come true. This adorable and affordable Vacation Home is located on the eve
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House Pet Friendly
$85 - $265 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
**Captain's Rest is now Flex-Stay ALL year long!**We travel not to escape Life, but so that Life doesn't escape us. It's so hard to find time to break away from the daily grind and spend time with those who matter most - but, we all know there's nothing more important. Make time to make Memories, because we've got the place for you! Welcome to Capt
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Captains Rest
Town House
$150 - $575 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 7 guests
Life is simple….just add water!The way we live today is crazy - we’re always in a hurry! Work, school, meetings, repeat. It’s so hard to find the time to gather those who mean the most to simply BE together. This is where “Stacked Deck” comes in - this home was made for making family memories together!This spectacular Waterfront Home is Brand New a
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Stacked Deck
House
$175 - $600 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 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 - $563 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Deja Blue - there is no color quite like this…..You know that feeling when you see the Ocean and all your worries just wash away? That’s the feeling you get as soon as you walk through the French Doors at Deja Blue on Chincoteague Island. This adorable Cottage oozes that quintessential Chincoteague Charm you love, plus has the Modern Amenities you
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House
$90 - $225 / per night
Bedrooms 2 bedrooms
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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Condominium Pet Friendly
$125 - $524 / 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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