Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

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

Welcome to beautiful Chincoteague Island, also known as Our Little Island by the Sea! 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
‘At the Water’s Edge’ - is there anywhere you’d rather be?! Welcome to this absolutely stunning Brand New Luxury Townhome on Marsh Island - just across the Channel from Chincoteague Island. As you take the exit for Marsh Island from the Causeway, you'll feel like you're pulling onto your own private island. With only a handful of homes here, you'l
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At the Waters Edge
Town House
$135 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
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
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Catch of the Day
Town House
$110 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 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
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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Lily Pad
House Pet Friendly
$85 - $294 / per night
Bedrooms 3 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
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Off the Record
House Pet Friendly
$135 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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
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Island Sage
House
$90 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague Lovers for years. Located less than 5 minutes from Assateague National Seashore, and allowing short stays all year long, it’s the perfect Vacation getaway for singles, couples, or small families. Assateague Inn 100-2R is actually
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Assateague Inn 100-2R
Condominium
$45 - $355 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
May you always have a shell in your pocket, and sand in your shoes…..Sandy Bottoms - the name alone stirs up fond memories of family vacations from long ago. This wonderful 4 Bedroom Home is brand new to the Seaside Vacations’ Family, and we couldn’t be happier - and it’s ready to make your Vacation Dreams come true!With Classic Coastal Cape good l
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Sandy Bottoms
House
$128 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 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 - $258 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 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
High Tides and Good Vibes…..Welcome to Tranquil Tides Retreat - a newly renovated and beyond adorable Waterfront Townhome located on Marsh Island, directly across the Channel from Chincoteague Island. Perfect for a small family or a couples getaway, you can take that beach break you’ve been longing for - without breaking the bank!As you take the ex
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Tranquil Tides Retreat
Town House
$125 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 4 guests
Sunset Bay 307 - Sometimes you just have to go with the Waves…..Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! 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 an
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Sunset Bay Villa 307 - Picasso
Condominium
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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