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 216 properties available
Heron Creek - Relax, Rejuvenate, and Reconnect…..Life is busy - schedules, school, meetings, and games - it’s nonstop. When was the last time you spent time with those who matter most simply playing - relaxing - giggling - making memories sure to last a lifetime?If this is what you’ve been yearning for, just wait til we tell you about fabulous Hero
Hot HOT 12
Heron Creek
Town House Pet Friendly
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Lighthouse Overlook - Every day should be a Beach Day…..Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Lighthouse Overlook was made
Lighthouse Overlook
House
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Have you ever asked yourself what the purpose of life is? Here at Seaside, we believe it’s all about spending time with those that matter most, and making memories you’ll cherish forever. And if you can make the time, we’ve got the most amazing home to tell you about…..Welcome to The Porpoise of Life in the very heart of Chincoteague Island. This
Hot HOT 5
The Porpoise of Life
House
$150 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!The most treasured heirlooms are the sweet memories of Family......Blue Heron is located in Eagle's Sound Estates, only 10 minutes from wonderful Chincoteague Island, Home of the Famous Wild Ponies and Misty of Chincoteague, yet you will feel as if you are in your own private Paradise. T
Hot HOT 7
Blue Heron
House
$175 - $325 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Whispering Pines, salty breezes, and chirping Tree Frogs - ahhhh. Can't you just picture yourself here right now? Beach Pines is a delightful Vacation Home located on Piney Island, which the is the closest community to Assateague National Seashore on Chincoteague Island. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our countr
Hot HOT 9
Beach Pines
House
$115 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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
Hot HOT 8
Beachgrass Bungalow
House Pet Friendly
$99 - $325 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Life is a collection of Moments….Longing for a new Experience - a different kind of Beach Getaway? Let us introduce you to a truly ‘Hidden Gem’ in Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia!Captain’s Cove is only 25 short minutes by boat or car from Chincoteague Island and Assateague National
Hot HOT 8
Hidden Gem
House
$145 - $328 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Relax, Rejuvenate, and Reconnect…..Welcome to ‘Shellfish Time’ on the beautiful Eastern Shore of Virginia! If you have been looking for a “different” kind of Vacation - a totally new Experience, yet not too far from Home, boy, do we have the place for you! Get ready for an awesome Adventure at this fabulous Brand New Home - the Beach, Wild Ponies,
Hot HOT 5
Shellfish Time
House Pet Friendly
$125 - $281 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Coastal Crab in Captain’s Cove - Just another day in Paradise…..There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at beautiful Coastal Crab in Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly on the C
Hot HOT 19
Coastal Crab
House
$150 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Hot HOT 6
z-7234 Oak Ridge Place
Town House
Memories at the Beach last a lifetime…..Hoping to land the big one this year for your Chincoteague Island Vacation? Look no further than adorable “Catch of the Day” on super quiet and peaceful Tim Lane, just off Deep Hole Road, in the very heart of Chincoteague Island!This delightful Duplex sits tucked at the end of the Lane, surrounded by peaceful
New Flex Stay! New Flex Stay!
New Flex Stay!
Catch of the Day
Town House
$110 - $274 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 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
Hot HOT 12
No Problem
Town House
$89 - $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.