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 213 properties available
Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When was the last time you broke away from the day-to-day with those who matter most? Well, the time is now, and the Vacation Destination is Gray Pearl in the heart of Chincoteague Island. This beautiful Canal Front Home is located in prestigi
Hot HOT 16
Gray Pearl
House
$350 - $725 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 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
Hot HOT 7
Breezy Corner
House
$90 - $285 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 7 guests
Rented!
Z-2283 Brigantine
House
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
Hot HOT 13
Assateague Inn 208-S
Condominium
$45 - $202 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 2 guests
Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Little Red Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Str
Hot HOT 5
Little Red Cottage
House
$100 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Welcome to Dolly's Place 6!Tucked away in a peaceful setting just a short stroll from the Sea Shell Motel and the beach, the Cottages offer the perfect blend of comfort, convenience, and classic Eastern Shore charm. This property features 2 Cottages, both sitting behind Dolly’s House. All of this, and just minutes from one of the most pristine and
Hot HOT 13
Dolly's Place 6
Cottage
$125 - $232 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sunsets are proof that no matter what happens, every day can end beautifully - and there is no better place to take in one of our famous Chincoteague Sunsets than fabulous Waterfront Wonder (formerly Sunset Foals). With gorgeous Newly Refinished, but still Historic, Hardwood Floors, and other upgrades, Waterfront Wonder still oozes the quintessenti
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Waterfront Wonder
House Pet Friendly
$125 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Black Skimmers are known for their unique grace as they forage in flight - the same can be said for this one-of-a-kind Vacation Home on Chincoteague Island. There's nothing quite like this beautiful Home that combines the Modern Amenities you want and need, with Historic Touches of yesteryear that only a Home born in the 1940's can offer. Located i
Hot HOT 12
Black Skimmer
House Pet Friendly
$196 - $750 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Ava’s Beach Cottage - Relax, Rejuvenate, and Reconnect…..Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ava’s Beach Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern
Hot HOT 14
Ava's Beach Cottage
House Pet Friendly
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
‘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
Hot HOT 23
Off the Record
House Pet Friendly
$135 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous Pier Pressure 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 has something for everyone in the family. Located at the water’s edge dir
Hot HOT 8
Pier Pressure
House
$125 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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
Hot HOT 32
Water's Edge
Town House
$100 - $350 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 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.