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 214 properties available
Sometimes you just have to go with the waves…..Looking to catch a beach getaway at a family-friendly price? Then look no further than Fishhook Hideaway on Deep Hole Road - truly the catch-of-the-day! This adorable 2 Bedroom/2 Full Bath home is located in the heart of our little Island - just a short stroll from Maddox Boulevard, Steamers, and The I
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Fishhook Hideaway
Town House
$75 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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z-2325 Rudder Ct
z-2325 Rudder Ct
House
**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
Calypso - Dance to the Song of the Sea.....You know that feeling you get while relaxing on the beach and listening to steel drums play while the Sea Breeze blows through your hair? Enjoy this feeling every day at fabulous Calypso in Captain's Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 4 B
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Calypso
House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Have you always wanted to Vacation on Chincoteague Island, but couldn't bear the thought of 4 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 Sunrise Serenade at Sea Tag Lodge, formerly "Sea Tag # 24". These fabulous Condos are located directly on the Assateague Channel with some of t
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Sunrise Serenade
Condominium
$65 - $200 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Good Vibes happen on the Tides…..Welcome to High Tide Hideaway - Brand New Construction in July 2023! Tucked in the very heart of our Little Island by the Sea on Church Street, you’re close to everywhere you want to be. Downtown Main Street Shops and Restaurants are just a short stroll away, as is our famous Farmers Market! You’ll love wandering do
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House Pet Friendly
$150 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Welcome to Ocean East 1 on the Eastside of Chincoteague Island.  This lovely End-Unit Townhome has it all - a comfortable layout, sweeping Views of the Assateague Channel and Lighthouse, Water Access, and even welcomes your well-trained Family Dog!As you enter Ocean East 1, all eyes will be on your breathtaking Views - you can already feel yourself
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Town House Pet Friendly
$90 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to The Pearl at Marsh Island - leave your troubles at the door, you won't be needing them here! This super charming and newly renovated 1 Bedroom/1 Bath Condo is on the 1st Floor, and will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel, the Causeway, a
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Condominium Pet Friendly
$75 - $195 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... Welcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination t
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Whelks on Willow
House
$173 - $600 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Live your Life by a compass, not a clock….Work, school, traffic, homework, repeat - right?! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Breathe - you’re on Island Time now. And boy, do we hav
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Happy Hideaway
House
$85 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
“Life is a journey that is not measured in miles or years, but in Experiences.” ~ Jimmy BuffettClose your eyes and feel the salty, sweet bay breeze wash over you. Breathe in the smell of Coppertone - hear the Gulls cry above. This is the very essence of Lammers Largo in beautiful Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on
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House
$195 - $524 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 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
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House Pet Friendly
$125 - $275 / 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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