Chincoteague Rentals With Pools

Chincoteague Rentals with Pool Access

Browse Chincoteague Rentals with Pool Access

Need a rental with more options than just the open water of the VA shore? Check out these Chincoteague Island Rentals with pools. With over 30 vacation homes and condos with pools or pool access, you are sure to have plenty of swim time and water fun. Each Chincoteague vacation rental provides several amenities to ensure a fun-filled vacation and a great location to the major attractions, shops, and dining.

Chincoteague Island has lots to do for your vacation. After a day at the beach, followed by lounging in your vacation rental's pool, maybe be a little adventure is what you need. Check out Maui Jacks Water Park & other fun activities on our Entertainment and Activities page!


Properties Available 59 properties available
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 14
The Sweets Spot
House
$135 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 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 17
Gallops Point
House Pet Friendly
$160 - $625 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 over the course
Hot HOT 18
Assateague Inn 204-S
Condominium
$45 - $334 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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 over the course
Hot HOT 9
Assateague Inn 206-S
Condominium
$45 - $338 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 almost brand new, and beyond stunning. Tucked Can
Hot HOT 24
Octopus's Garden
House
$125 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 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
Hot HOT 22
Off the Record
House Pet Friendly
$135 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Cove’s Point - Of all the paths you take in life, make sure a few of them are sandy…….When was the last time you had a vacation that took your breath away? If this is what you’ve been craving, Cove’s Point is the place for you. Located in gorgeous Captain’s Cove Golf and Yacht Club - one of the best kept secrets on the Eastern Shore of Virginia, yo
Hot HOT 19
Coves Point
House
$135 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Bella Vista - Everything is better with a Water View…..Welcome to Sunset Bay 319 - Bella Vista - at fabulous Sunset Bay Villas on the Chincoteague Bay. Bella Vista, which is Italian for ‘beautiful View’, more than lives up to its name with stunning Direct Bayfront Views all around. These gorgeous condos sit directly on the Bay with spectacular View
Hot HOT 17
Sunset Bay Villa 319 - Bella Vista
Condominium
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Black Skimmers are known for their unique grace as they forage in flight - the same can be said for this one-of-a-kind Vacation Home on Chincoteague Island. There's nothing quite like this beautiful Home that combines the Modern Amenities you want and need, with Historic Touches of yesteryear that only a Home born in the 1940's can offer. Located i
Hot HOT 17
Black Skimmer
House Pet Friendly
$175 - $700 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
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 over the course
Hot HOT 16
Assateague Inn 208-S
Condominium
$45 - $313 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
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 over the course
Hot HOT 14
Assateague Inn 209-S
Condominium
$65 - $378 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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
Hot HOT 19
Casa Del Sol
House
$200 - $625 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests

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