Chincoteague Rentals With Pools

Chincoteague Rentals with Pool Access

Browse Rentals with Pool Access

Need a rental with more options than just the open water of the Virginia 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 Island vacation rental provides several amenities to ensure a fun-filled vacation and great locations near 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 64 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 10
Assateague Inn 207-S
Condominium
$45 - $251 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 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 24
Sunset Bay Villa 309 - Changes in Latitude
Condominium Pet Friendly
$150 - $425 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Stunning Updates!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
Hot HOT 18
Assateague Inn 111-2R
Condominium
$45 - $251 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Ready for a Vacation that will take your breath away?! We’ve got the perfect place for you - welcome to fabulous Pier Pressure 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 dir
Hot HOT 19
Pier Pressure
House
$125 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 13
Casa Del Sol
House
$200 - $550 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sitting Waterfront on Eel Creek, you'll enjoy lovely Views!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
Hot HOT 10
Assateague Inn 213-2R
Condominium
$45 - $233 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Welcome to Fletcher House #8 on Willow Street! The Fletcher House Cottages have been helping families make amazing Chincoteague Memories for decades! Once part of the The Sea Shell Motel, these cottages are now part of our Seaside Vacations’ Family! And, Fletcher House Guests have access to the Outdoor Pool at the Sea Shell Motel nearby!This adorab
Hot HOT 5
Fletcher House #8
Cottage
$102 - $474 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Isn't it time for a new romance.....with Life?! A visit to fabulous Bay Pony is certainly the place to begin. This phenomenal End-Unit Townhome is located in a wonderful little community, Silver Sails. One of the most unique and wonderful features of this Neighborhood is that it has a spectacular seasonal Community Swimming Pool for you to enjoy af
Hot HOT 17
Bay Pony
Town House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Make all of your Chincoteague Vacation Dreams come true in this adorable 3 Bedroom, 1 1/2 Bath Historic Home in the heart of Chincoteague Island. Tucked on Willow Street, you’ll be just a hop, skip, and jump away from our Beach - Assateague National Seashore - where our famous Wild Ponies roam free, as well as the shops and restaurants of our Histo
Hot HOT 10
Dolly's House #4
House
$150 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 8 guests
Our Memories of the Ocean live on, long after our footprints are gone….Making Memories - isn’t that what it’s all about? Escaping from the daily grind, and reconnecting with those who matter most. Kids grow up fast, and life is so short - the Beach is calling - and we have the perfect homebase for your next Chincoteague Island adventure….Welcome to
Hot HOT 9
MoManna Retreat
Town House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Life is a collection of Moments….Longing for a new Experience - a different kind of Beach Getaway? Let us introduce you to a truly ‘Hidden Gem’ 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 boat or car from Chincoteague Island and Assateague National
Hot HOT 14
Hidden Gem
House
$145 - $329 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 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 16
Heron Creek
Town House Pet Friendly
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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