Chincoteague Rentals - Flex Stay Vacations
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 Island vacation rentals with Flexible Stays, so you can check-in on your schedule.
102 properties available
Ava’s Beach Cottage - Relax, Rejuvenate, and Reconnect…..Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe Ava’s Beach 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
Welcome to Chris' Cottage 1!Tucked away in a peaceful setting just a short stroll from the Sea Shell Motel and the beach, Chris’ Cottages offer the perfect blend of comfort, convenience, and classic Eastern Shore charm. This property features three identical cottage-style units, thoughtfully updated and designed for a relaxing coastal getaway. All
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
“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
If you’ve been longing for a totally different vacation experience, we cannot wait to introduce you to The Pearl at Wallops, tucked on 4.5 acres in beautiful Wallops Island, less than 15 minutes from Chincoteague Island and Assateague National Seashore, where our famous wild ponies roam free! What makes The Pearl at Wallops so special, you ask?This
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
Travel - It leaves you speechless, then turns you into a Storyteller…..When was the last time you took a Vacation that took your breath away? If you’ve been looking for that one-of-a-kind Vacation Experience, we’d love to introduce you to ‘House on the Dune’ in the prestigious Wildcat Community on Chincoteague Island. This stunning Custom Home is 1
Our Memories of the Ocean live on, long after our footprints are gone….Making Memories - isn’t that what it’s all about? Escaping from the daily grind, and reconnecting with those who matter most. Kids grow up fast, and life is so short - the Beach is calling - and we have the perfect homebase for your next Chincoteague Island adventure….Welcome to
Beachgrass Bungalow - High Tides and Good Vibes….The best things in Life are the people we love, the places we’ve been, and the memories we make along the way…..Life is busy - plain and simple. Work, meetings, schedules, lessons - pretty much chaos - all the time! This makes breaking away from the day to day more important than ever. Pack a bag, gr
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
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
The Teal on Eel Creek - Beach Days are the Best Days…..Just imagine relaxing on the Deck taking in that salty, sweet bay breeze - listening to the Tree Frogs sing - and watching Herons, Eagles, and Egrets fish for their morning meal in Eel Creek just behind the house…..This is living the shore life at The Teal on Eel (formerly Oyster Bay Hideaway)
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