Pet Friendly Rentals
Seaside Vacation Rentals provides families with a wide selection of Chincoteague rentals, some even that are Pet Friendly! Now you don't have to leave anyone behind on your next vacation; bring your family dog with you. The entire family can enjoy the Chincoteague shoreline, several pet friendly establishments, and a well-deserved vacation.
Each Chincoteague Island Vacation rental provides your family with quality amenities, spacious rooms, and prime location to all of Chincoteague's attractions, dining, and shopping, Choose from 2-4 bedroom rentals...all pet friendly.
Browse below and start planning your next Chincoteague vacation today!
66 properties available
Trees listen to the Breeze; and then rustle its voice so beautifully….Looking for a getaway that makes you feel a million miles from the real world? Just imagine kicking back under the shade of tall Pine Trees - swaying in the breeze, while you listen to the Tree Frogs sing - pure bliss. Whispering Pines is not just a place to lay your head at nigh
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
Beach More, Worry Less…..If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New Addition to our Seaside Family has it all - that quintessential Chincoteague Charm you love, the Modern Amenities you want and need, and a fabulous Mid-Island Location - close to everywhere you want to be!Shore to Please is tucked on
Welcome to Oasis on Main — a charming retreat nestled in the heart of Chincoteague Island. This beautifully updated home sits right on Historic Main Street, offering the perfect blend of island convenience and peaceful seclusion. Step out front to explore the shops, galleries, and restaurants, just a short stroll away, or slip out back to your own
There’s only one thing more precious than our time, and that is who we spend it on. Even in today’s world, it isn’t always easy to find true quality time with those who matter most. There are Zoom meetings and virtual lessons - the days are still demanding, and perhaps even more stressful than ever. Making that special time for nothing more than ‘t
“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
You work hard all year long. When the time is right, you’re looking for just the right place to slow down, and spend some hard earned quality time with the ones who matter most in your life. Well, look no further! We have the place you’ve been dreaming about! Lola B’s Bayside Bungalow is a cozy 2 Bedroom/2 Bath home tucked back in Ocean City’s ever
Sugar Shores - Your next Vacation can be both Salty and Sweet!When was the last time you had a Vacation that took your breath away? It’s the perfect combination of the right Destination, the right Vacation Home, and the perfect Location. Sugar Shores on beautiful Chincoteague Island is all of that and more, and only a few minutes from Assateague Na
Life takes you down many paths, but our favorite ones always lead to the Beach….There’s nothing like the smell of salt in the air and a warm breeze through your hair - the complete feeling of freedom that engulfs you the moment you know your Vacation is about to begin. And that’s what you’ll find at Bay Breeze in fabulous Captain’s Cove Golf and Ya
Welcome to Reel Nauti at Ocean Village! A fabulous 2nd floor condo tucked in a quiet community in West Ocean City, close to OCMD, Assateague, and everywhere you want to be. The community of Ocean Village is centered around a large pond with a gazebo and relaxing fountain, and the community offers Pickleball, Basketball, Tennis, a kids Playground, a
You work hard all year long, right?!. When the time is right, you’re looking for just the right place to slow down, and spend some hard earned, quality time with the ones who matter most in your life. Well, look no further. We have the place you’ve been dreaming of! Bayside Blue is an absolutely charming 3 Bedroom/2 Bath Bayfront Home tucked back i
The very definition of ‘Amistad’ is friendship - and that suits this beautiful home so well, as you’ll feel like you’re visiting a long, lost friend on our Little Island by the Sea. You’ll love making unforgettable family memories in this charming historic home that has graced Chincoteague Island with its presence since the early 1900’s. With the q
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