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
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
Hot HOT 27
Octopus's Garden
House
$125 - $412 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 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 8
Shellfish Time
House Pet Friendly
$125 - $246 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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 18
Sunset Bay Villa 216
Condominium
$150 - $375 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Dolly's Place 6!Tucked away in a peaceful setting just a short stroll from the Sea Shell Motel and the beach, the Cottages offer the perfect blend of comfort, convenience, and classic Eastern Shore charm. This property features 2 Cottages, both sitting behind Dolly’s House. All of this, and just minutes from one of the most pristine and
Hot HOT 16
Dolly's Place 6
Cottage
$125 - $225 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 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
Hot HOT 61
Sunset Bay Villa 209
Condominium Pet Friendly
$125 - $525 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 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 11
Dolly's House #4
House
$150 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 1 bath
Guests 8 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 - $213 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Life takes you down many paths, but our favorite ones always lead to the Beach….There’s nothing like the smell of salt in the air and a warm breeze through your hair - the complete feeling of freedom that engulfs you the moment you know your Vacation is about to begin. And that’s what you’ll find at Bay Breeze in fabulous Captain’s Cove Golf and Ya
Hot HOT 39
Bay Breeze
House Pet Friendly
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
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 11
Bay Pony
Town House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Black Skimmers are known for their unique grace as they forage in flight - the same can be said for this one-of-a-kind Vacation Home on Chincoteague Island. There's nothing quite like this beautiful Home that combines the Modern Amenities you want and need, with Historic Touches of yesteryear that only a Home born in the 1940's can offer. Located i
Hot HOT 35
Black Skimmer
House Pet Friendly
$198 - $750 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 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 11
Assateague Inn 205-S
Condominium
$45 - $218 / 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 9
Assateague Inn 204-S
Condominium
$45 - $206 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests

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

I agree