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.
109 properties available
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 Ducks, Docks, and Flip Flops - what more could you want, right? This recently renovated and beyond adorable Waterfront Townhome is located on Marsh Island, directly across the Channel from Chincoteague Island. Offering amazing Channel Views and a Community Dock, it is the perfect Vacation Destination for a couples getaway or small family
Have you always wanted to vacation on Chincoteague Island, but couldn't bear the thought of 6 of you in a hotel room? Love the idea of a Vacation Home, but don't want to break the bank? Welcome to Dancing Waters at Sea Tag Lodge, sitting directly on the Assateague Channel! The Sea Tag Lodge has been helping families make amazing memories for decade
Welcome to Bradford House - proof that great things can indeed come in small packages! Y’all, a stay at Bradford House feels like a stay with old friends. There’s a warmth and coziness about it that hits you as soon as you walk in - it just feels like home. Tucked in a great location on School Street, you’ll feel a million miles away from the real
Wonderview 208 ~ Take the Journey to enjoy the View…..Life gets busy - work, kids, appointments, pets - it never seems to stop. This makes it more important than ever to take time to stop and smell the roses - or more appropriately, the salty, sweet sea breeze. If you can make the time, we most definitely have the place….Welcome to fabulous Wonderv
Welcome to Island Bay Dreams in the very heart of Chincoteague Island! This absolutely adorable 4 Bedroom Townhome truly has it all, and is less than 10 minutes away from Assateague National Seashore, where our famous Wild Ponies roam free!You know when you walk into a home and instantly feel your worries vanish? That’s exactly the vibe we get from
Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sitting Waterfront on Eel Creek, you'll enjoy lovely Views!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
Welcome to Go with the Flow — your laid-back waterfront escape on Marsh Island, just across the channel from Chincoteague Island. Here, days move at the pace of the tide, with salty breezes, glowing sunsets, and front-row seats to island life. Whether you’re sipping coffee on the deck or watching boats drift by, this is a place where you can truly
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
Memories are timeless treasures of the heart….When was the last time you took a Vacation that truly touched your heart and took your breath away? They aren’t easy to find, but when you do, you never forget the special moments and the memories that were made. Belle Vue is THIS kind of Vacation - an Experience that you will never forget, not just a p
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
Welcome to Chris' Cottage 2!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
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