Chincoteague 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
171 properties available
Reach for the Stars on your next Chincoteague Island Vacation…..Welcome to whimsical Starbright Cottage on beautiful Chincoteague Island! This adorable 4 Bedroom home is not only in an amazing mid-Island location, it welcomes your whole family - including your friendly Dog! Starbright Cottage has the allure of a bygone era, combined with the modern
Bliss by the Bay - If you’re wearing flip flops, you’re overdressed!There’s nothing like the smell of salt in the air and a warm breeze through your hair - and that’s just what you’ll find at Bliss by the Bay in beautiful Captain’s Cove Golf and Yacht Club. One of the best kept secrets on the Eastern Shore of Virginia, Captain’s Cove sits directly
Happy Pines has some great updates for 2024 including New Floors throughout and updated Bathrooms!As you turn onto Pine Creek Drive, you will feel the hustle and bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Be
Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….”Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Little Red Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Str
Ready to have a ‘Shell of a Time’ on your next trip to our Little Island by the Sea?! You will absolutely fall in love with this beautiful Cottage on Chincoteague Island - tucked on a quiet street, but close to everywhere you want to be! Shell of a Time has all that you love about a quintessential Chincoteague Cottage, plus the Modern Amenities you
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
Travel - the only thing you pay for that makes you richer. But, you don't have to break the bank to have the Vacation of your Dreams on Chincoteague Island - welcome to fabulous Island Retreat! This adorable Duplex sleeps 7 in comfort and style, has amazing Water Views, AND welcomes your family's dog!Island Retreat is in the perfect location, just
Lily Pad has had some BIG updates this year - New Flooring in the Kitchen, New Furnishings, New Washer and Dryer, and the addition of a Dishwasher!Lily Pad on beautiful Chincoteague Island is the perfect place to make your Vacation Dreams come true. This adorable and affordable Vacation Home is located on the ever-popular East Side, tucked on a qui
Serenity Now - It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by c
Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ocean Pearl Cottage, but the words comfy, cozy, and charming come to mind. This quintessential Chincoteague Cottage is just a short stroll from Main Street Restaurants, Shops, and Robert Reed Waterfront Park - home to THE most ama
Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is
**Captain's Rest is now Flex-Stay ALL year long!**We travel not to escape Life, but so that Life doesn't escape us. It's so hard to find time to break away from the daily grind and spend time with those who matter most - but, we all know there's nothing more important. Make time to make Memories, because we've got the place for you! Welcome to Capt
Tell us what you're looking for and someone will contact you with available options.