Chincoteague Rentals - Flex Stay Homes
Here at Seaside Vacations, we understand how busy life is, and that you can't always get away for a full week. That's what we LOVE about our Flex Stay Program ~ Arrive when you want, depart when you want, the world is your Oyster (it's a Chincoteague thing)! The homes in our Flex Stay Program have either a 2 or 3 night minimum all year long, not just the Off-Season! As always, we're standing by ready to help you find just the right home for your next Beach Break!
Browse these amazing Chincoteague Rentals with Flexible Stays so you can check-in on your schedule and not by a schedule set for you.
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81 properties available
Longing to get away from it all and leave the busy world behind - even for a just a little while? We cannot think of a better getaway than lovely Oystercatcher on Chincoteague Island. This beautiful Duplex that sleeps 6 more than comfortably is in the very heart of our special Island. Located on Ridge Road, only steps from famous Pony Swim Lane, yo
“Not all who wander are lost…..”Welcome to Lily Pad 2 in the very heart of Chincoteague Island! If you’ve been looking for the perfect place to “get lost”, yet still be close to everywhere you want to be, this is the place for you! Brand New Lily Pad 2 sits tucked down a quiet Lane, and is the sister-house to Lily Pad on Wayne Road, sitting almost
Shell Shack - High Tides and Good Vibes….When was the last time you took a Vacation that truly took your breath away?! If you have been looking for a true Vacation Experience - not just a place to lay your head at night - boy, do we have a wonderful surprise for you - welcome to Shell Shack!This incredible home is Brand New to our Seaside Family, a
“Rainbows and Mermaids are proof that imagination and beauty go hand in hand.”Welcome to The Mermaid Lounge on Chincoteague Island. An absolutely adorable and affordable Beach getaway tucked on the ever-popular East Side - close to everywhere you want to be!If you’re not familiar with the East Side, imagine driving down a quiet road that hugs the s
Wind Rose has some great updates including a New Outdoor Shower and Arcade1Up Pac-Man Legacy Machine with 12 different games! Now Dog Friendly with a $100 Pet Fee each!Wanderlust - "a strong desire or urge to wander or travel and explore the world." Have YOU experienced the beauty and wonder of Chincoteague Island yet? Beautiful Wind Rose is the p
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
Whispering Pines, salty breezes, and chirping Tree Frogs - ahhhh. Can't you just picture yourself here right now? Beach Pines is a delightful Vacation Home located on Piney Island, which the is the closest community to Assateague National Seashore on Chincoteague Island. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our countr
The best things in life are the people we love, the places we’ve been, and the memories we’ve made together….Feel like you’re going a million miles an hour every single day? We get it - life is so busy that it’s hard sometimes to just find time to BE together. But it’s so important to gather those who matter most and make it happen, and we’ve got
Sea Breeze - Life’s at ease with an Ocean Breeze…..Close your eyes and imagine breathing in that salty, sweet air - the sound of the Gulls, the Watermen harvesting Oysters - you’re beginning to relax, and you’re not even here yet! This is a feeling deep in your soul - this is Sea Breeze…..Located on Marsh Island, you'll have amazing Views of both B
Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague Lovers for years. Located less than 5 minutes from Assateague National Seashore, and allowing short stays all year long, it’s the perfect Vacation getaway for singles, couples, or small families. Assateague Inn 100-2R is actually
Bella Vista - Everything is better with a Water View…..Welcome to Sunset Bay 319 - Bella Vista - at fabulous Sunset Bay Villas on the Chincoteague Bay. Bella Vista, which is Italian for ‘beautiful View’, more than lives up to its name with stunning Direct Bayfront Views all around. These gorgeous condos sit directly on the Bay with spectacular View
Welcome to Waterfront Sunsets - Sunsets are proof that no matter what happens, every day can end beautifully…..This adorable Efficiency Condo will make you feel a million miles away from the real world. Located on Marsh Island, you'll have amazing Views of both Black Narrows Channel, the Causeway, and the Chincoteague Channel. Perfect for a Romanti
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