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!
61 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
The Sweets Spot
House
$135 - $350 / per night
4
bedrooms
3
baths
8
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
Anchors Away
House
$79 - $760 / per night
3
bedrooms
3
baths
6
guests
Sunset Bay 110 - Relax, Rejuvenate, Reconnect....Sunset Bay 110 is now DOG FRIENDLY with a $100 Pet Fee *PER PET*! Must be pre-approved and max of 2.Welcome to Sunset Bay 110 - Hawk’s Nest - 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
Sunset Bay Villa 110 - Hawk's Nest
Condominium
$150 - $425 / per night
3
bedrooms
2
baths
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
Off the Record
House
$135 - $325 / per night
3
bedrooms
2
baths
6
guests
Relax, Rejuvenate, and Reconnect…..Welcome to Brand New ‘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, Wi
Shellfish Time
House
$125 - $300 / 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 103-S
Condominium
$45 - $319 / per night
1
bedroom
1
bath
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
Assateague Inn 100-2R
Condominium
$45 - $356 / per night
2
bedrooms
2
baths
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
Assateague Inn 205-S
Condominium
$45 - $319 / per night
1
bedroom
1
bath
4
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 - $525 / per night
3
bedrooms
2
baths
8
guests
Sunset Bay 307 - Sometimes you just have to go with the Waves…..Welcome to Sunset Bay 307 - Picasso - at fabulous Sunset Bay Villas on the Chincoteague Bay - truly a work of Art! 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 an
Sunset Bay Villa 307 - Picasso
Condominium
$125 - $375 / per night
3
bedrooms
2
baths
6
guests
The Baywatch Bungalow - If you’re not barefoot, then you’re overdressed…..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 Kept Secrets on the Eastern S
The Baywatch Bungalow
House
$125 - $295 / per night
3
bedrooms
2
baths
6
guests
Assateague Inn 102 had a facelift in 2022, and is beachy and beautiful - check it out!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,
Assateague Inn 102-S
Studio
$45 - $340 / per night
1
bedroom
1
bath
4
guests
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