Chincoteague Island Vacation Rentals
Browse over 100 Chincoteague 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. Check out what we can offer you today!
Seaside Vacations offers so many wonderful vacation home rentals from Chincoteague Island to the Mainland. Select from our large choice of Chincoteague Waterfront Vacation Rentals or Rentals with Pools.
160 properties available
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
We are big believers that every Home has a story.......a story rich in happiness and sadness, struggles and successes - that creates its very essence. The C-Ray Cottage has a story you will love.......This adorable Bayfront Waterman's Cottage exudes that quintessential Chincoteague Charm. The C-Ray Cottage is the former working office of C. Ray Jes
The Happy Crab - Where dreams are made of Sun and Sand…..There's only one thing more precious than our time, and that is who we spend it on. Life is busy - just getting the family together can be such a challenge in today's world, but nothing is more important than doing just that. Clear the calendar, grab those you love, and head to Chincoteague I
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Painted Pony Cottage, but the word Charming is the first to come to mind. This quintessential Chincoteague Cottage simply oozes it. The perfect blend of Yesteryear and Modern Amenities, there's no better home base for making Chinc
Sunny Shack - The Best Days are Beach Days..…..Welcome to Sunny Shack on wild and wonderful Chincoteague Island! This stunning Waterfront Dream Home is brand new to the Seaside Vacations’ Family, but has been a fan-favorite Vacation Rental for years!Ahhhh, South Main Street - if you aren’t familiar, South Main is home to some of THE most amazing Su
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
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 Brand New 2021 Construction, and beyond stunning.
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!The most treasured heirlooms are the sweet memories of Family......Blue Heron is located in Eagle's Sound Estates, only 10 minutes from wonderful Chincoteague Island, Home of the Famous Wild Ponies and Misty of Chincoteague, yet you will feel as if you are in your own private Paradise. T
“Life is a journey that is not measured in miles or years, but in Experiences.” ~ Jimmy BuffettClose 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 Lammers Largo in beautiful Captain’s Cove Golf and Yacht Club - one of the Best Kept Secrets on
Give me the Sea and a little Cottage just to be….The first time we saw ‘Crepe Myrtle Cottage’, we felt an inviting warmth pulling us in. Very difficult to describe, it’s the feeling of true Southern Charm, mixed with the appeal of modern amenities and chic decor. To us, it is the absolutely perfect combination of the quintessential Chincoteague Cot
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
The welcome mat is out at spectacular Ariel's Grotto - only minutes from Assateague National Seashore, home of the Famous Wild Ponies! This 3 Bedroom/2.5 Bath Home is simply stunning. Located on a very quiet street mid-island, this awesome Chincoteague Vacation Home is sure to make all of your Vacation Dreams come true!As you enter this Coastal Ca
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