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
Island Days and Sunny Rays…..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, Marsh, 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 fi
Hot HOT 20
Sunset Bay Villa 306 - Our Pleasure
Condominium Pet Friendly
$125 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... Welcome to Whelks on Willow - a lovely Coastal Cape Cod tucked away on Willow Street - close to everywhere you want to be, yet a million miles away from the worries of the real world. Featuring a refreshing Private Pool, Whelks on Willow is truly a Vacation Destination t
Hot HOT 21
Whelks on Willow
House
$140 - $550 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Assateague Inn 107 in the heart of Chincoteague Island at the The Assteague Inn. The Inn is a long time favorite of Beach Lovers, and sits less than 5 minutes from Assateague National Seashore, where our Wild Ponies roam free!What makes Assateague Inn 107 different from the other Suites at this beloved building? It’s the ONLY Suite that
Hot HOT 21
Assateague Inn 107-A
Condominium
$65 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Relax, Rejuvenate, and Reconnect…..Welcome to ‘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, Wild Ponies,
Hot HOT 25
Shellfish Time
House Pet Friendly
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Of all the paths you take in life, make sure a few of them are sandy…..Welcome to ‘Paradise’ on dreamy Chincoteague Island - it’s not just a vacation home, it’s a feeling - relax, rejuvenate, and reconnect with those who matter most at this gorgeous Waterfront Townhome nestled directly on the Chincoteague Bay.Tucked away in the perfect location on
Hot HOT 14
Paradise
Town House
$145 - $549 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - a Water Lover’s 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
Hot HOT 39
Sunset Bay Villa 310 - Nauti Girl
Condominium Pet Friendly
$150 - $475 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
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 11
Serenity Now
House
$250 - $395 / 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 9
Assateague Inn 206-S
Condominium
$45 - $300 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Heron Creek - Relax, Rejuvenate, and Reconnect…..Life is busy - schedules, school, meetings, and games - it’s nonstop. When was the last time you spent time with those who matter most simply playing - relaxing - giggling - making memories sure to last a lifetime?If this is what you’ve been yearning for, just wait til we tell you about fabulous Hero
Hot HOT 22
Heron Creek
Town House Pet Friendly
$150 - $459 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Changes in Latitude, Changes in Attitude….Jimmy Buffet sure does know what he’s talking about, doesn’t he?! 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
Hot HOT 34
Sunset Bay Villa 309 - Changes in Latitude
Condominium Pet Friendly
$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 37
Sunset Bay Villa 216
Condominium
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Bliss by the Bay - If you’re wearing flip flops, you’re overdressed!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 Bliss by the Bay in beautiful Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly
Hot HOT 40
Bliss by the Bay
House
$125 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

Tell us what you're looking for and someone will contact you with available options.

I agree