Pet Friendly Rentals

Pet Friendly Vacation Rentals

Seaside Vacation Rentals provides families with a wide selection of Chincoteague rentals, some even that are Pet Friendly! Now you don't have to leave anyone behind on your next vacation; bring your family dog with you. The entire family can enjoy the Chincoteague shoreline, several pet friendly establishments, and a well-deserved vacation.

Each Chincoteague Island Vacation rental provides your family with quality amenities, spacious rooms, and prime location to all of Chincoteague's attractions, dining, and shopping, Choose from 2-4 bedroom rentals...all pet friendly.

Browse below and start planning your next Chincoteague vacation today!


Properties Available 69 properties available
Beach More, Worry Less…..If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New Addition to our Seaside Family has it all - that quintessential Chincoteague Charm you love, the Modern Amenities you want and need, and a fabulous Mid-Island Location - close to everywhere you want to be!Shore to Please is tucked on
Hot HOT 31
Shore to Please
House Pet Friendly
$95 - $350 / per night
Bedrooms 5 bedrooms
Bathrooms 1 bath
Guests 10 guests
Reach for the Stars on your next Chincoteague Island Vacation…..Welcome to whimsical Starbright Cottage on beautiful Chincoteague Island! This adorable 4 Bedroom home is not only in an amazing mid-Island location, it welcomes your whole family - including your friendly Dog, with NO ADDITIONAL FEE! Starbright Cottage has the allure of a bygone era,
Hot HOT 17
Starbright Cottage
House Pet Friendly
$125 - $400 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 9 guests
You work hard all year long. Now is the time to slow down, and spend some hard earned, quality time with the ones who matter most in your life. Well, look no further, we have the place you’ve been dreaming about! 116 Pine Forest Drive is an absolutely stunning, newly constructed 5 Bedroom, 4 Bath home tucked back in Ocean Pines South community, wit
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116 Pine Forest Drive
House Pet Friendly
$175 - $934 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
The Sea, once it casts its spell, holds one in its net of wonder forever……When was the last time you had a Vacation that truly took your breath away? An OCMD Vacation where you could bring the whole family together - even the family dog! We’d like to introduce you to ‘Sea Salt’ ~ an absolutely stunning Townhome only steps from the Beach, the Bay, a
Hot HOT 46
Sea Salt
Condominium Pet Friendly
$169 - $1,300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Trees listen to the Breeze; and then rustle its voice so beautifully….Looking for a getaway that makes you feel a million miles from the real world? Just imagine kicking back under the shade of tall Pine Trees - swaying in the breeze, while you listen to the Tree Frogs sing - pure bliss. Whispering Pines is not just a place to lay your head at nigh
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Whispering Pines
Town House Pet Friendly
$145 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Nestled in the serene community of Ocean Pines, 60 White Tail Circle, a spacious two-story home that offers an ideallic blend of comfort, and convenience, promising an unforgettable getaway for the family longing for a relaxing escape. From the moment you arrive, you'll be greeted by the tranquil ambiance of this fabulous community with Coastal adv
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60 White Sail Circle
House Pet Friendly
$129 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Life’s a Beach - If you’re not barefoot, you’re overdressed….When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for just the right place - or just the right Experience, we should say - boy, do we have the place for you! K and S Paradise is nestled right in the heart of Chincoteague Islan
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K and S Paradise
House Pet Friendly
$100 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Surf Crest 101 - Let the waves kiss your feet, and the sand be your seat!Have you been yearning for a little sun and sand? Perhaps a Beach Break that won’t break the bank? If you can make the time, we certainly have the place! Surf Crest 101 is a delightful Newly Remodeled Condo in the very heart of OCMD. With a great Downtown Location, you are clo
Hot HOT 30
Surf Crest 101
Condominium Pet Friendly
$100 - $650 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Travel - the only thing you pay for that makes you richer. But, you don't have to break the bank to have the Vacation of your Dreams on Chincoteague Island - welcome to fabulous Island Retreat! This adorable Duplex sleeps 7 in comfort and style, has amazing Water Views, AND welcomes your family's dog!Island Retreat is in the perfect location, just
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Island Retreat
Town House Pet Friendly
$70 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Tucked back in the quiet North Ocean City neighborhood of Caine Woods is a simply decadent home we call Twin Tree. This much loved 4 Bedroom, 3 Bath home with a Loft and Garage is exactly the perfect space for the family, or families, looking to experience Ocean City, the Beach and all our great town has to offer, while still being able to settle i
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Twin Tree
House Pet Friendly
$226 - $1,100 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 14 guests
Memories made together last a lifetime…..Welcome to Oyster Bay Oasis in ever-popular Oyster Bay I on Chincoteague Island - the perfect home base for your family’s next adventure! Only 5 minutes from Assateague National Seashore, where our Wild Ponies roam free, this adorable home has all the quintessential Chincoteague Charm you love, plus the mod
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Oyster Bay Oasis
House Pet Friendly
$99 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 6 guests
Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 18, located in the very heart of Chincoteague Island. This lovely Townhome is convenient to everywhere you want to be on our beautiful Island, yet a quiet and peaceful Retreat at the day's end. And, there's no need to leave Fido ou
Hot HOT 66
Eastwinds 18
Town House Pet Friendly
$70 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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