Chincoteague Vacation Rentals

Chincoteague Island Vacation Rentals

Browse over 150 Chincoteague Island Rentals, all at the Best Rates

Welcome to beautiful Chincoteague Island! Are you ready for a vacation away from the big city and crowded beach resorts? A Chincoteague Vacation Rental means that there are no high-rises, boardwalks, or traffic jams to interfere with your relaxation. We offer beautiful rentals to fit any family size or group gathering, all at the lowest rates around. Come see the wonder of Chincoteague Island, include famous events such as the Pony Swim!

Seaside Vacations offers so many wonderful vacation house rentals from Chincoteague Island to the Mainland. Select from our large choice of Chincoteague Waterfront Vacation Rentals or Rentals with Pools.


Popular Chincoteague Island Rentals

House Rentals | Condo Rentals | Waterfront Rentals | Rentals with Pools | Pet Friendly Rentals | Communities


Properties Available 175 properties available
Beach More, Worry Less…..If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New Addition to our Seaside Family has it all - that quintessential Chincoteague Charm you love, the Modern Amenities you want and need, and a fabulous Mid-Island Location - close to everywhere you want to be!Shore to Please is tucked on
Hot HOT 21
Shore to Please
House Pet Friendly
$95 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 1 bath
Guests 10 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 19
Heron Creek
Town House Pet Friendly
$150 - $425 / 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 19
Sunset Bay Villa 309 - Changes in Latitude
Condominium Pet Friendly
$150 - $495 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Marsh Madness - Because saltwater is simply good for the soul…..**Marsh Madness now sleeps 12 and is Dog Friendly with a $100 Pet Fee per dog! AND, has a fully enclosed fence in the backyard!Break away from the daily grind at Marsh Madness - leave your troubles at the door, you won't be needing them here! This incredibly unique Waterfront Home trul
Hot HOT 50
Marsh Madness
House Pet Friendly
$175 - $700 / per night
Bedrooms 5 bedrooms
Bathrooms 2 baths
Guests 11 guests
Take a Vacation that makes you forget to check your cell phone….Looking to leave the real world behind - just for a few days? Grab those who matter most, and clear your calendar - Caribbean Ketch is waiting for you! This charming home is located in the ever-popular Piney Island, which happens to be the closest community to Assateague National Seash
Hot HOT 7
Caribbean Ketch
House
$125 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
*Assateague Inn 211 has had some great updates for 2024 including new Flooring and a totally new bathroom including shower with grab bars, some new furnishings, and new art! 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 w
Hot HOT 20
Assateague Inn 211-S
Condominium
$45 - $348 / per night
Bedrooms 1 bedroom
Bathrooms 1 bath
Guests 4 guests
Calypso - Dance to the Song of the Sea.....You know that feeling you get while relaxing on the beach and listening to steel drums play while the Sea Breeze blows through your hair? Enjoy this feeling every day at fabulous Calypso in Captain's Cove Golf and Yacht Club - one of the Best Kept Secrets on the Eastern Shore of Virginia. This stunning 4 B
Hot HOT 22
Calypso
House
$150 - $375 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Looking for an incredible Chincoteague Island Vacation Experience? You just found it at Sea Treasure - a beautiful Duplex that sleeps 6 more than comfortably in the very heart of our special Island. Located on Ridge Road, right next to famous Pony Swim Lane, you can relax on your Screened Porch and take in amazing Views of Assateague Island and our
Hot HOT 15
Sea Treasure
Town House
$85 - $250 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
Welcome to Albion and the best Chincoteague Island Vacation you have ever had! This phenomenal, one-of-a-kind dream home is located on Willow Street, right in the heart of the island, and near everywhere you want to be. Lush, tropical landscaping will welcome you as you pull into the custom circular driveway, with parking for 3 cars. This spectacul
Hot HOT 12
Albion
House
$126 - $450 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
So, you'd like to be only minutes from the Beach, close to Shopping and Dining, able to walk to the park that has THE best Sunsets anywhere, and stay in an affordable, yet awesome Vacation Home? You may think that is a tall order for us to fill, but it's not! Welcome to Victoria Cottage on Church Street - This truly delightful 3 Bedroom/ 2.5 Bath V
Hot HOT 12
Victorian Cottage
House
$85 - $265 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Life is good, but Island Life is better!Looking for a Beach Break that will take your breath away, yet not break the bank? Welcome to The Teague House on peaceful and serene Marsh Island! This Newly Renovated Townhome in Captain’s Quarters Townhomes has it all, and is just a stone’s throw from our beautiful Little Island by the Sea!As you take the
Hot HOT 26
The Teague House
Town House
$89 - $275 / per night
Bedrooms 2 bedrooms
Bathrooms 1 bath
Guests 6 guests
GREAT UPDATES FOR 2023!! Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 18, located in the very heart of Chincoteague Island. This lovely Townhome is convenient to everywhere you want to be on our beautiful Island, yet a quiet and peaceful Retreat at the day's end. And, there's
Hot HOT 19
Eastwinds 18
Town House Pet Friendly
$70 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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