Chincoteague House Rentals

Chincoteague Island Home Rentals

Take the vacation you and your family deserve! Enjoy the open, less-crowded, and beautiful surroundings of Chincoteague Island, VA. No vacation is complete without the perfect place to stay. Check out the large selection of Chincoteague Home Rentals. Select from waterfront homes, pet-friendly houses, and houses with pool access.

A Chincoteague House Rental provides more than just a cozy place to rest your head. Each home is packed with amenities, such as FREE WiFi, furnishing, close proximity to all attractions, shopping, and dining on Chincoteague.

Browse our selection below and start planning the vacation you and your family deserve! You can also browse all of our Chincoteague Rentals here.


Properties Available 115 properties available
Fabulous Updates for 2022!!"We cannot control the wind, but we can direct the sail" - Life is busy. It gets more and more difficult to find that cherished time with family and friends. This is the sole purpose of Smooth Sailing on Chincoteague Island. It is a retreat. A destination. A place to rejuvenate and reconnect with those who matter the most
Hot HOT 16
Smooth Sailing
House
$135 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Collect Memories, not things…..Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moments together that used to be easy to find, are hard to come by these days. This is why we must MAKE them happen! So, clear the calendar and grab those who matter most - we’ve got the Vacation of a lifetime for you right here on Chinco
Hot HOT 31
Teal Cottage
House
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Were you dazzled by your last Vacation? If not, you clearly weren’t staying at absolutely stunning and Brand New ‘Gallops Point’ 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 has something for everyone in the family. Located at the water’s edge o
Hot HOT 52
Gallops Point
House Pet Friendly
$175 - $625 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you've been longing for - tucked away on a quiet lane in the heart of our tiny Island. George's Retreat is in the perfect location, just off of Maddox Boulevard, aka the Beach Road - you can walk or ride your bike to many, Restaurants
Hot HOT 18
Georges Retreat
House
$75 - $240 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Life takes you down many paths, but our favorite ones always lead to the Beach….There’s nothing like the smell of salt in the air and a warm breeze through your hair - the complete feeling of freedom that engulfs you the moment you know your Vacation is about to begin. And that’s what you’ll find at Dockside Dreams in fabulous Captain’s Cove Golf a
Hot HOT 20
Dockside Dreams
House Pet Friendly
$115 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Relax, Rejuvenate, and Reconnect…..Welcome to Brand New ‘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, Wi
Hot HOT 45
Shellfish Time
House Pet Friendly
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Looking for somewhere truly special to spend your Chincoteague Island Family Vacation this year? Look no further, as special doesn't even begin to describe the tranquility and beauty of waterfront Family Tides. This adorable home is located directly on Lewis Creek's deep water, so by all means, bring the boat, kayaks, jet skis, or water toy of choi
Hot HOT 23
Family Tides
House
$135 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Octopus’s Garden - “I’d like to be under the Sea ~ in an Octopus’s Garden in the shade!”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! Octopus’s Garden is Brand New 2021 Construction, and beyond stunning.
Hot HOT 16
Octopus's Garden
House
$125 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Flex Stay Home - Captain's Cove doesn't allow Arrivals or Departures on Sundays. A day spent at the Beach is never a wasted day…..Ready for a Vacation that will thrill everyone in your family? You’ve found ‘The Sweets Spot’ right here in Captain’s Cove, for sure! Captain’s Cove Golf and Yacht Club is one of the Best Kept Secrets on the Eastern Shor
Hot HOT 28
The Sweets Spot
House
$135 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
The welcome mat is out at spectacular Ariel's Grotto -  only minutes from Assateague National Seashore, home of the Famous Wild Ponies! This 3 Bedroom/2.5 Bath Home is simply stunning. Located on a very quiet street mid-island, this awesome Chincoteague Vacation Home is sure to make all of your Vacation Dreams come true!As you enter this Coastal Ca
Hot HOT 35
Ariels Grotto
House
$90 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Little Red Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Str
Hot HOT 28
Little Red Cottage
House
$100 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Serenity Now -  It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by c
Hot HOT 14
Serenity Now
House
$250 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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