Seaside Vacations & Sales Chincoteague Island

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 les

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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!

The weekend is almost here, and Chincoteague Island is the place to be! 🌞🏖️If you're visiting this weekend, there's no s...
08/06/2026

The weekend is almost here, and Chincoteague Island is the place to be! 🌞🏖️

If you're visiting this weekend, there's no shortage of ways to make the most of these beautiful summer days:

🗼 Climb the iconic Assateague Lighthouse for breathtaking views
🚀 Explore NASA's FREE STEM Spotlight Series
🦥 Make your way to Christ United Methodist Church to experience Coastal Wilds' Mobile Zoo
🏴‍☠️ Discover the island's fascinating history on a Pirate, Legend & Lore Tour
🎶 Grab a lawn chair and enjoy a FREE concert at Robert Reed Park on Saturday evening!

As we soak in these last weeks of summer, there's never been a better time to experience everything Chincoteague Island has to offer. The crowds are slowing thinning out, so whether you're looking for adventure, history, music, or simply to relax, unforgettable memories are waiting around every corner.

Who's ready for an island weekend?! 🌊☀️

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

✨Testimonial Tuesday✨THIS is why we do what we do, y'all!There is nothing more rewarding than welcoming first-time visit...
08/04/2026

✨Testimonial Tuesday✨

THIS is why we do what we do, y'all!

There is nothing more rewarding than welcoming first-time visitors to Chincoteague Island and hearing that they completely fell in love with it. We feel incredibly lucky to call this little island home, and sharing its beauty, charm, and traditions with others is something we're truly passionate about. ❤️

Every glowing review reminds us why we love what we do. Thank you ALL for trusting Seaside Vacations to be a part of your family's memories year after year.

08/03/2026

What an amazing Pony Swim Week! 🐴❤️

To everyone who stayed with us, visited the island, and helped celebrate another incredible year of this cherished tradition—thank you! We already can't wait to do it all again. 🫶

Want to be sure you secure the PERFECT vacation rental for your trip into town for next year? Reservations for the 2027 Pony Swim are now open! Secure your stay with just a 35% deposit, and your remaining balance isn't due until 30 days before your arrival. Pay a little each month or wait and pay it all at once before the 102nd Pony Swim—the choice is yours!

Visit SeasideVacations.Rentals or give our team a call at (757) 336-7070 and let our team help you start planning your dream vacation today!

🎶 Pony Swim Week may be over... but the fun on Chincoteague is far from finished! 🌅Join us TONIGHT at Robert Reed Park f...
08/01/2026

🎶 Pony Swim Week may be over... but the fun on Chincoteague is far from finished! 🌅

Join us TONIGHT at Robert Reed Park for a FREE Family Concert featuring Backroad! Co-sponsored by the Chincoteague Cultural Alliance (CCA) and Seaside Vacations, this is the perfect way to wrap up an incredible week on the island.

Enjoy an evening filled with:🎵 Amazing live music🌅 Breathtaking sunset views over the water💃 Plenty of toe-tapping, dancing, and family fun!

The concert begins at 7:00 PM, so grab your blankets or lawn chairs, bring your family and friends, and come spend a beautiful summer evening with us.

We'll see you at Robert Reed Park! 🎸☀️

07/31/2026

The most beautiful morning possible for the 2026 Swim Back to conclude Pony Swim week! Thanks again to Bottom's Up Tiki Tours for having us aboard with a front row seat!

Reminder that you can start booking your 2027 Pony Swim trip with Seaside Vacations TOMORROW, August 1st, 2026! If you're ready to cross Pony Swim off your bucket list, or are ready for another one, it's never too early to start planning!

Until next year, y'all! 🐴❤️

That’s all, folks! 🌅🐴🌊2026 Pony Swim Week was a wonderful success! The Swim Back has concluded, and thanks to Bottom's U...
07/31/2026

That’s all, folks! 🌅🐴🌊

2026 Pony Swim Week was a wonderful success! The Swim Back has concluded, and thanks to Bottom's Up Tiki Tours we had a front row seat to the most beautiful morning of the week! Huge thanks to Capt. Erik for having us aboard and knowing exactly how to get a great view both during the swim back, and once the ponies had crossed over!

The ponies who will remain with the herd are safely back on Assateague, and Chincoteague’s biggest week of the year is officially drawing to a close.

Our heartfelt thanks go to everyone who makes this treasured tradition so successful, beautiful, and stress-free—the dedicated volunteers and organizers, Saltwater Cowboys and Cowgirls, carnival workers, first responders, community partners, and the many others working behind the scenes.

It truly takes an island, and we’re incredibly grateful for every person who helped make this unforgettable week possible.

Remember that we can begin accepting reservations for the 2027 Pony Swim TOMORROW, AUGUST 1ST!!! If you're ready to rebook for next year, or are ready to cross Pony Swim off your bucket list, it's NEVER too early to start planning! 🐴

Until next year! 🐴❤️

07/31/2026

It’s time for the Swim Back as another incredible Pony Swim week comes to a close!

How wonderfully fitting is it that today is the International Day of Friendship?! 🐴❤️After today’s Pony Auction (that ra...
07/30/2026

How wonderfully fitting is it that today is the International Day of Friendship?! 🐴❤️

After today’s Pony Auction (that raised over $630,000 for our Volunteer Fire Department,) dozens of families are heading home with a brand new friend-or, better yet, the newest member of their families!

Here’s to the special bonds that are beginning today and all of the love, adventures, and unforgettable memories to come. Congratulations to every pony and their new family!

07/30/2026

Today, dreams will come true! 🥰

Happy Auction Day! 🐴❤️

07/29/2026

The 101st Annual Pony Swim was a picture perfect morning on Chincoteague Island!

Seaside’s very own Collin the C**t made his return to the island after some years away in Blacksburg, and he LOVED the new perspective and seeing his old friends and family!

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

Website

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