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

s.....

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!

09/14/2026

Sometimes, the best way to start the day is to let the waves set the pace. 🌊

✨ NEW TO SEASIDE: SUNKISSED SHORES 🌅🏡Say hello to Sunkissed Shores, one of the newest additions to the Seaside Vacations...
09/12/2026

✨ NEW TO SEASIDE: SUNKISSED SHORES 🌅🏡

Say hello to Sunkissed Shores, one of the newest additions to the Seaside Vacations family, and trust us, this one is something special! 😍

Located directly on the Chincoteague Bay in the prestigious Wildcat community, Sunkissed Shores combines luxury, waterfront living, and FUN to create an island getaway the entire family will love.

🌅 Breathtaking Bay Views — The sunsets here have to be seen to be believed!

🎣 Private Pier — Spend your mornings fishing, launch the kayaks for an afternoon adventure, or simply sit back and enjoy life on the water.

🛏️ 4 Bedrooms + 4 Full Baths — Every bedroom has its own full bathroom, giving everyone plenty of space and privacy.

🕹️ An Entertainment Area Made for Family Fun — Head upstairs and take your pick from more than 2,500 classic arcade games, Giant Connect 4, chess, and a massive flat-screen TV. Rainy days have officially met their match!

🦀 Enclosed All-Weather Gazebo — Unwind with a drink, take in the waterfront atmosphere, or gather the whole family around the table for an Eastern Shore seafood feast!

Whether your perfect Chincoteague vacation means kayaking across the bay, fishing from your own pier, challenging the kids to an arcade tournament, sharing steamed crabs with the family, or watching the sun disappear over the water, Sunkissed Shores gives you the perfect place to do it all. ❤️

Click the link below to see more of this stunning new addition to the Seaside family, or give our team a call at (757) 336-7070 for more information on rates and availability!

🏠: https://www.seasidevacations.rentals/rentals/sunkissed-shores

🇺🇸 Chincoteague Remembers. Chincoteague Honors. Chincoteague Will Never Forget.This Patriot Day, we pause to remember th...
09/11/2026

🇺🇸 Chincoteague Remembers. Chincoteague Honors. Chincoteague Will Never Forget.

This Patriot Day, we pause to remember the thousands of lives lost on September 11, 2001, and the countless families whose lives were forever changed.

We honor the courage of the first responders who ran toward danger, the bravery of everyday civilians who stepped forward to help others, and the men and women who have served and sacrificed in the years since.

25 years later, we continue to remember the lives lost, the heroes who emerged, and the strength and unity our nation showed in the face of unimaginable tragedy.

Today, and always, Chincoteague remembers. 🇺🇸

For years, Seaside Vacations has worked to stay involved in advocacy throughout the vacation rental industry because we ...
09/10/2026

For years, Seaside Vacations has worked to stay involved in advocacy throughout the vacation rental industry because we knew conversations like those happening on Chincoteague today would eventually come.

Following the Town Council’s recent hearing regarding short-term rentals, one of our owners, Lance, had the opportunity to speak with WBOC about issues that could have a lasting impact on property owners, visitors, local businesses, and our community as a whole.

We believe there should be a short-term rental ordinance in place. We also believe it’s incredibly important that it’s done the right way.

That means doing the research. Listening to the people who will be affected both directly and indirectly. Looking at real data. Understanding how proposed changes could impact our local economy, property owners, residents, businesses, and generations of families who return to Chincoteague year after year. Most importantly, it means carefully considering the long-term effects before decisions are made that could reshape the future of our island.

To our property owners: We want you to know that we are ALWAYS working to represent you. Your homes are more than vacation rentals — they’re hard-earned investments, and often times homes that you plan to retire to sooner rather than later. We take seriously our responsibility to advocate for fair, thoughtful policies that protect both your property and its future.

To our guests: We’re advocating for you, too! We want families to continue experiencing Chincoteague the way they have for generations — staying together, creating memories together, and returning to the island they love without new occupancy restrictions potentially forcing larger families and groups to book multiple properties just to enjoy their vacation together.

And to our community: We believe thoughtful regulation and a thriving vacation rental industry can coexist. Our goal has never been to avoid regulation. It’s to make sure the policies put in place are researched, balanced, enforceable, and created with input from everyone whose lives and livelihoods they may affect.

We love this island. We live here. We work here. We raise our families here. And we’ll continue showing up, listening, researching, and advocating for solutions that protect what makes Chincoteague special while helping ensure its future remains bright. ❤️

09/09/2026

Why pay more when you don’t have to?!

When you book your next beach getaway directly with Seaside Vacations, you can save HUNDREDS of dollars compared to booking through Airbnb or VRBO — meaning more money in your pocket and more to spend enjoying the island! 🌊☀️

Skip the extra fees. Book direct. Vacation More.

Your vacation starts with the right booking.

https://www.seasidevacations.rentals/

Testimonial Tuesday! Thanks so much Kevin for choosing to stay with Seaside Vacations for your visit to the island! We'r...
09/08/2026

Testimonial Tuesday!

Thanks so much Kevin for choosing to stay with Seaside Vacations for your visit to the island! We're so glad to hear you enjoyed your experience booking with us. Stress free vacations are our ultimate goal, and we're always happy to hear when we've delivered!

We can't wait to have you back on Chincoteague!

https://www.seasidevacations.rentals/rentals/whispering-pines

🇺🇸 Happy Labor Day from Chincoteague Island! 🇺🇸Today, we're celebrating the hardworking people who make everything we do...
09/07/2026

🇺🇸 Happy Labor Day from Chincoteague Island! 🇺🇸

Today, we're celebrating the hardworking people who make everything we do possible—from our incredible Seaside Vacations team and local business owners to everyone taking a well-earned day to relax with the people they love most.

Whether you're spending the day exploring the island, enjoying fresh local seafood, spotting wildlife on Assateague, paddling the waterways, or simply unwinding by the water, we hope your Labor Day is filled with sunshine, laughter, and unforgettable moments.

Thank you for choosing Chincoteague to make your memories. We hope you have a safe, happy, and relaxing Labor Day! ❤️🤍💙

"This is the happiest place on Earth"Yes. Yes, it is. 🥰🏝️Thanks so much to everyone who came out tonight for the final M...
09/07/2026

"This is the happiest place on Earth"

Yes. Yes, it is. 🥰🏝️

Thanks so much to everyone who came out tonight for the final Music at the Dock concert of the 2026 season! The entire evening was perfect from the performance to the sunset that took place as the band was beginning to wind down. 🎶🥁🌅

We love being a part of these special events that bring the community and visitors together, and are already looking forward to next year!

Until then! ❤️

09/07/2026

🎶 What a way to close out the summer! 🎶

A heartfelt thank you to everyone who joined us at Robert Reed Waterfront Park this evening for an unforgettable performance by C.A.I.S.O.!

From the incredible crowd and the band's fun, high-energy performance to the breathtaking sunset that painted the sky as the music began to wind down, it was one of those evenings that reminds us just how special Chincoteague truly is. Moments like these are what summer is all about.

To everyone who came out to enjoy the Music at the Dock concert series throughout the summer—thank you. Whether you attended one concert or every single one, your smiles, dancing, and support helped make this another amazing season.

A special thank you to the Chincoteague Cultural Alliance, the talented musicians who shared their gifts with our community, and everyone who helped make these evenings possible.

We're already counting down the days until we can do it all again next summer. Until then, thank you for making another season of Music at the Dock one to remember. ❤️🌅🎶

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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