Chincoteague Rentals With Pools
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!
57 properties available
“The Ocean stirs the heart, inspires the imagination, and brings eternal Joy to the Soul.” ~ R. WylandWhen was the last time you experienced the pure Joy of time spent with those who matter most - away from all the distractions of our daily lives? Work, school, chores, homework - the hamster wheel seems to never stop spinning. It’s more important n
A Shore Joy
House
$200 - $700 / per night
4
bedrooms
2
baths
10
guests
Mmmmm., 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
Assateague Inn 104-S
Condominium
$45 - $348 / per night
1
bedroom
1
bath
4
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
Assateague Inn 111-2R
Condominium
$45 - $349 / per night
2
bedrooms
2
baths
4
guests
Casa Playa - Peace, Love, and Sandy Feet……Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Casa Playa is all about - kicking back, tak
Casa Playa
House
$100 - $275 / per night
3
bedrooms
2
baths
6
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
Off the Record
House
$135 - $325 / per night
3
bedrooms
2
baths
6
guests
Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague Lovers for years. Located less than 5 minutes from Assateague National Seashore, and allowing short stays all year long, it’s the perfect Vacation getaway for singles, couples, or small families. Assateague Inn 100-2R is actually
Assateague Inn 100-2R
Condominium
$45 - $391 / per night
2
bedrooms
2
baths
4
guests
Ahhh, Chincoteague Island—where the salty breeze of the marsh tickles your senses and wild ponies roam free, painting a picture straight out of a dream. Once you step foot on our little slice of paradise, it’s like leaving a piece of your heart behind. But let’s be real—life gets busy. Taking off for a full week every year? Not always easy. Maybe y
Assateague Inn 203-S
Condominium
$45 - $353 / per night
1
bedroom
1
bath
4
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
Sunset Bay Villa 216
Condominium
$150 - $375 / per night
3
bedrooms
2
baths
6
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
Octopus's Garden
House
$125 - $450 / per night
4
bedrooms
3
baths
8
guests
Welcome to Sunset Bay 109 at fabulous 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 Comm
Sunset Bay Villa 109
Condominium
$125 - $514 / per night
3
bedrooms
2
baths
8
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
Paradise
Town House
$145 - $549 / per night
3
bedrooms
2
baths
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
Assateague Inn 209-S
Condominium
$65 - $393 / per night
1
bedroom
1
bath
4
guests
Copyright © 2025 • Seaside Vacations Rentals
All Rights Reserved.