Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

Browse over 150 Chincoteague Island Rentals, all at the Best Rates

Welcome to beautiful Chincoteague Island! Are you ready for a vacation away from the big city and crowded beach resorts? A Chincoteague Vacation Rental means that there are no high-rises, boardwalks, or traffic jams to interfere with your relaxation. We offer beautiful rentals to fit any family size or group gathering, all at the lowest rates around. Come see the wonder of Chincoteague Island, include famous events such as the Pony Swim!

Seaside Vacations offers so many wonderful vacation house rentals from Chincoteague Island to the Mainland. Select from our large choice of Chincoteague Waterfront Vacation Rentals or Rentals with Pools.



Properties Available 180 properties available
Ahhh, Chincoteague Island—the salty marsh breeze, the iconic wild ponies, and that magical feeling you can’t quite put into words. Once you’ve been here, it’s like the Island calls you back again and again. Sometimes life gets busy, and not everyone has the time to sneak away for a whole week. Maybe you’re more of a Weekend Warrior type, grabbing t
Hot HOT 19
Assateague Inn 109-S
Condominium
$45 - $338 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sunset Bay 110 - Relax, Rejuvenate, Reconnect....Sunset Bay 110 is now DOG FRIENDLY with a $100 Pet Fee *PER PET*! Must be pre-approved and max of 2.Welcome to Sunset Bay 110 - Hawk’s Nest - at fabulous Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on the Bay with stunning Views of the Bay, Drawbridge
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Sunset Bay Villa 110 - Hawk's Nest
Condominium Pet Friendly
$150 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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
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Blue Heron
House
$175 - $300 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 9 guests
Welcome to Casa Del Sol - “Live in the Sunshine, swim the Sea, drink the Wild Air….”When was the last time your Vacation took your breath away? If that is what you’ve been yearning for, clear your schedule - Paradise awaits you in beautiful Captain’s Cove Golf and Yacht Club!Casa Del Sol is Brand New Construction in 2024, and beyond stunning. Tucke
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Casa Del Sol
House
$200 - $625 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 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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Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Island Sage on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This cozy Vacation Home is just that - a HOME, not just a place to lay your head at night. Located in popular Piney Island, which happens to be the closest community to Assateague National Seashore, you will lo
Hot HOT 13
Island Sage
House
$90 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
This lovely Home is the perfect Vacation Destination for your next Beach Getaway. Located on Lewis Creek, you'll enjoy stunning Views of Lewis Creek and the Chincoteague Bay - simply magical in every way. Lewis Creek is a Nature Lover's Dream - teeming with life. Watch Herons and Egrets fish for their morning meal from the Screened Porch or your up
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Channel View Cottage
House
$200 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
Give me the Sea and a little Cottage just to be….The first time we saw ‘Crepe Myrtle Cottage’, we felt an inviting warmth pulling us in. Very difficult to describe, it’s the feeling of true Southern Charm, mixed with the appeal of modern amenities and chic decor. To us, it is the absolutely perfect combination of the quintessential Chincoteague Cot
Hot HOT 15
Crepe Myrtle Cottage
House
$90 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Ahhh, Chincoteague Island—where the salty marsh breeze greets you, and wild ponies roam Assateague as if they’re welcoming you home. One trip here, and it’s love at first sight—it’s the kind of place that sticks with you forever. But let’s face it, life’s a whirlwind, and carving out a whole week to escape isn’t always in the cards. Maybe you’re mo
Hot HOT 11
Assateague Inn 110-S
Condominium
$45 - $334 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Sky above, Sand below, Peace within….Life is short - and busy - OH, so busy. When was the last time you grabbed those who matter most and left it all behind, even if just for a few days?! If you’ve been longing for a Beach Break, we’ve got the perfect place for you, right here in the very heart of Chincoteague Island! Welcome to The Virginia Lee -
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The Virginia Lee
House Pet Friendly
$99 - $315 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Salty air breezes and the sweet serenity of pond-front living await you at The Pearl at Grand Bay. This Newly Remodeled End Unit Townhome has it all - magnificent Water Views, and a stunning interior. Located on the ever-popular East Side, you can have the Chincoteague Vacation you’ve been dreaming of at a very family-friendly price tag - and even
Hot HOT 14
The Pearl at Grand Bay
Town House Pet Friendly
$99 - $300 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
GORGEOUS updates!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
Hot HOT 17
Assateague Inn 105-S
Condominium
$45 - $338 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

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