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 55 properties available
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 17
Assateague Inn 206-S
Condominium
$45 - $366 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Casa Del Canal - Captivating. Canalfront. Calling your name.....Looking for the perfect Eastern Shore Vacation Destination? Look no further than Casa Del Canal in gorgeous Captain's Cove - one of the best kept secrets on the Eastern Shore of Virginia. This stunning 3 Bedroom/2 Bath Waterfront Home has something for everyone in the family. Located C
Hot HOT 24
Casa Del Canal
House
$140 - $250 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Nothing soothes the soul like a day by the water…..If you love living at the water’s edge, we have the perfect Vacation Destination for you - with 360 degree gorgeous Water Views! Welcome to Anchors Away in Captain’s Cove Golf and Yacht Club! One of the Best Kept Secrets on the Eastern Shore of Virginia, Captain’s Cove is only 25 short minutes by c
Hot HOT 43
Anchors Away
House Pet Friendly
$54 - $800 / per night
Bedrooms 3 bedrooms
Bathrooms 3 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 15
Assateague Inn 207-S
Condominium
$45 - $366 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Coastal Crab in Captain’s Cove - Just another day in Paradise…..There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at beautiful Coastal Crab in Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly on the C
Hot HOT 25
Coastal Crab
House
$125 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
The Baywatch Bungalow - If you’re not barefoot, then you’re overdressed…..Beautiful Updates for 2023!!Close your eyes and feel the salty, sweet bay breeze wash over you. Breathe in the smell of Coppertone - hear the Gulls cry above. This is the very essence of The Baywatch Bungalow in beautiful Captain’s Cove Golf and Yacht Club - one of the Best K
Hot HOT 26
The Baywatch Bungalow
House
$125 - $295 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Assateague Inn 106 is like New for 2022! New Flooring, Cabinets, Renovated Bathroom, and Fresh Paint - it's gorgeous!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 aw
Hot HOT 36
Assateague Inn 106-S
Condominium
$45 - $366 / 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 18
Assateague Inn 211-S
Condominium
$45 - $366 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 26
Sunset Bay Villa 319 - Bella Vista
Condominium
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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
Hot HOT 70
Sunset Bay Villa 111
Condominium
$125 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
‘By the Bay’ - Is there anywhere you’d rather be?!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
Hot HOT 17
Sunset Bay Villa 313 - By the Bay
Condominium
$150 - $500 / per night
Bedrooms 3 bedrooms
Bathrooms 2 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 26
The Sweets Spot
House
$135 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests

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