Seaside Vacations & Sales Chincoteague Island

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Seaside Vacations & Sales Chincoteague Island 🏆 Best of Locals Choice 3 Years Running!
🏆 VRMA 2023 Vacation Rental Management Co. We Live here, we work here, we play here.

of the Year
🏆 VRMA 2024 Excellence Award for Community Impact
🏆 2025 VRMA Marketing Campaign of the Year

❤️Serving Chincoteague Island, Captain's Cove, & OCMD!❤️ Founded by Lance & Elaine Stitcher, SV is military family-owned & operated - We are YOUR Local Experts. We want to make this Vacation stress free for you - just sit back and enjoy the time with family and friends. Beach more, worry less.....

If you're a Homeowner, our Property Care, Technology, and Service is second to none. When you work with us, we aren’t just your property managers - you become a part of our Seaside family. If you've been dreaming of owning a little slice of our Paradise, we've got you covered there, as well! No one knows the Vacation Rental (2nd Home) Market better than we do - whether you're relocating or just looking for your own little getaway, our dedicated Local Team of Realtors has your back. Seaside Vacations & Sales - Let us help y'all Live the Shore Life!

🌟 Testimonial Tuesday 🌟Thank you, Peyton, for choosing to stay with us at The Pearl at Grand Bay! 🏡💙 We’re grateful you ...
10/13/2026

🌟 Testimonial Tuesday 🌟

Thank you, Peyton, for choosing to stay with us at The Pearl at Grand Bay! 🏡💙 We’re grateful you chose Seaside Vacations for your home away from home!

For anyone who loves spending their vacation outdoors, this home puts you in the perfect spot! With Memorial Park nearby, you can launch a kayak, cast a line, try your luck at crabbing, or enjoy some playground time with the kids. Looking for a little friendly competition? Head to the tennis or basketball courts and let the family vacation bragging rights begin! 🎣🛶🏀

After a day of fresh air and adventure, The Pearl at Grand Bay is ready to welcome you home to unwind and share your favorite moments.

Thanks again, Peyton—we hope to welcome you back for more island memories! ☀️

🔗: https://www.seasidevacations.rentals/rentals/the-pearl-at-grand-bay

🎉 Help us wish a very Happy Birthday to our Laundry Manager, Kevin! 🎂Kevin and his hardworking team are essential to kee...
10/12/2026

🎉 Help us wish a very Happy Birthday to our Laundry Manager, Kevin! 🎂

Kevin and his hardworking team are essential to keeping things running smoothly here at Seaside Vacations! He’s done an amazing job helping us refine our processes to ensure every guest arrives to fresh, clean linens—setting the stage for a comfortable, relaxing stay. It’s a big job behind the scenes, and we’re incredibly grateful for the care and dedication he brings to it. 🧺✨

But as much as we appreciate everything Kevin does, we appreciate the person he is even more. Always making time to stop in and say hello, Kevin brings a positive, upbeat energy that makes our days a little brighter. We’re lucky to have him as both a leader and a member of our Seaside family! 💙

Happy Birthday, Kevin! We hope your day is filled with the same happiness you bring to those around you. You deserve it!

What a day at the Oyster Festival! We’re still smiling thinking about all the fun we had. The food was amazing as always...
10/11/2026

What a day at the Oyster Festival! We’re still smiling thinking about all the fun we had. The food was amazing as always, but the best part of this festival will always be the people. Getting to catch up with our friends and family here in the community and meeting all the visitors who come to town to celebrate with us is what makes this event so special.

A huge thank you to everyone who stopped by, said hello, grabbed some goodies, and helped make this weekend one to remember. We’re already counting down the days until we get to do it all again at the Seafood Festival this spring!

10/10/2026

The gates are open! Happy Oyster Festival Day everyone! 🦪❤️

10/09/2026

🦪 Less than 24 hours until the seafood tents open at the Annual Oyster Festival!

Oyster season is officially here, and we can’t wait to celebrate with everyone! Stop by and see us at Seaside Vacations, right beside the band, where we’ll be handing out free goodies and celebrating the start of another oyster season alongside our amazing community.

Good seafood, good people, and a whole lot of Chincoteague spirit. We hope to see you all out there! 🦪🌊

🎃👻 A SPOOKTACULAR TIME AWAITS ON CHINCOTEAGUE ISLAND! 🍬🦇Looking for a new family Halloween tradition? We've got just the...
10/08/2026

🎃👻 A SPOOKTACULAR TIME AWAITS ON CHINCOTEAGUE ISLAND! 🍬🦇

Looking for a new family Halloween tradition? We've got just the thing! 🎃

Make your way to Chincoteague Island for Trick or Treat Main Street, a frightfully fun evening filled with Halloween magic for the entire family! 🧙‍♀️✨

Watch as our charming island downtown transforms into a Halloween wonderland, with local shops opening their doors to welcome little ghosts, goblins, superheroes, and princesses for a night of tricks, treats, and unforgettable memories! 🍭🍫

Come for the candy, stay for the memories, and discover just how BOO-tiful Chincoteague Island can be this time of year! 🧡🖤

https://www.seasidevacations.rentals/

⭐️ TESTIMONIAL TUESDAY ⭐️Imagine this…You wake up, make breakfast for the family, and head out for a day of Chincoteague...
10/06/2026

⭐️ TESTIMONIAL TUESDAY ⭐️

Imagine this…

You wake up, make breakfast for the family, and head out for a day of Chincoteague adventures. ☀️ Maybe it’s a day on the beach, a boat tour around the island, or simply exploring everything our little slice of paradise has to offer.

Then, you come back “home,” prepare a fresh seafood feast, and end the day soaking in your waterfront hot tub as the sky lights up with a breathtaking Chincoteague sunset. 🌅🦀

And once the sun disappears? Sit back, relax, and enjoy a little stargazing before calling it a night. ✨

Sounds pretty perfect, right? That’s exactly the kind of experience waiting for you at Shell Shack! 🏡💙

🔗: https://www.seasidevacations.rentals/rentals/shell-shack

🤠TEAM SEASIDE IS TAKING ON NASHVILLE!🤠Some of our team is currently in Music City for the annual Vacation Rental Managem...
10/05/2026

🤠TEAM SEASIDE IS TAKING ON NASHVILLE!🤠

Some of our team is currently in Music City for the annual Vacation Rental Management Association Conference!

Over the next few days, we’ll be diving into hands-on education, learning from others throughout the vacation rental industry, exploring new ideas, and bringing home knowledge that will help us continue to improve the Seaside experience for our guests, homeowners, and community.

No matter how far we've come, we believe there's always room to learn, grow, and get better. That's why we're committed to making sure our team has the knowledge, resources, and tools necessary to continue taking the quality of our service to the next level.

Because when our team gets better, everyone we serve benefits!

POV: You booked a beach weekend, but Mother Nature did too. 🌧️ During last week's Nor'Easter we shared some of our favor...
10/03/2026

POV: You booked a beach weekend, but Mother Nature did too. 🌧️

During last week's Nor'Easter we shared some of our favorite things to do when the weather doesn't cooperate, but now we want to know what YOUR favorite things to do are! Did we miss anything fun that your family loves to do on rainy days?

Let us know in the comments below, and help fellow visitors find plans for this rainy weekend!

🎉🌊  ! 🌊🎉We’ve FINALLY made it to everyone’s favorite day of the week! 🙌As the work week winds down, we hope you find a l...
10/02/2026

🎉🌊 ! 🌊🎉

We’ve FINALLY made it to everyone’s favorite day of the week! 🙌

As the work week winds down, we hope you find a little time to relax, have some fun, and enjoy a well-deserved break this weekend. Whether that means sleeping in, spending time with family, grabbing dinner at your favorite spot, or simply doing absolutely nothing, we support it!

And hey… while we’ve still got some beautiful weather hanging around, there’s always time to squeeze in one more long weekend at the beach before the chilly weather arrives! 👀🏖️

Pack a bag. Head to the coast. Make a few more memories before the big winter chill. Remember last winter?! 🥶

🔗: https://www.seasidevacations.rentals/

Address

4101 Main Street
Chincoteague, VA
23336

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 9am - 5pm
Sunday 9am - 4pm

Telephone

+17573367070

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