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

Seaside Vacations & Sales Chincoteague Island

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Chincoteague, VA
Seaside Vacations & Sales Chincoteague Island

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🏆 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!

10/31/2026

🎃Another Trick or Treat Main Street is in the books, and what a SPOOKTACULAR evening it was! 👻

We LOVE seeing Historic Downtown Chincoteague come alive with so many ghosts, goblins, superheroes, princesses, and everything in between! Some of those costumes were seriously creative, and we were blown away by how much effort everyone put into them!

Our favorite part? Seeing SO MANY smiling faces stop by our Seaside Vacations office throughout the evening! 🧡 There’s nothing quite like seeing our community come together for a night full of fun, laughter, and Halloween magic!

🎃 HAPPY HALLOWEEN from all of us at Seaside Vacations & Sales! We hope everyone had a frighteningly good time, and remember… don’t eat ALL of your candy tonight! 😉🍫🍭

10/31/2026

Happy Halloween 🎃 💀👻!

Trick or Treating is in full swing at ! Come by and see us for some sweet treats!

👻

10/30/2026

Please join us in welcoming Sunset Bay Villa 116 to the Seaside Vacations family! 🌅❤️

Our Sunset Bay condos are some of our most popular properties, and we’re so excited to add another beautiful option for your next Chincoteague getaway!

This spacious 3-bedroom, 2-bathroom condo has everything you need for a relaxing island escape, including:

✨ Amazing sunset views
🏊 Seasonal outdoor pool
💪 Fitness center
🛏️ Plenty of space for the whole family
📍 A fantastic location just minutes from historic Downtown Main Street

You’ll also be close to some of the island’s favorite dining spots, including Bill’s Prime Seafood & Steaks, The Ropewalk, and Don’s Seafood making it perfect for grabbing a delicious meal after a day of exploring!

Ready to see more, click the link below to take a closer look at Sunset Bay Villa 116, or give our team a call at (757) 336-7070 for more information on rates and availability!

🔗: https://www.seasidevacations.rentals/rentals/sunset-bay-villa-116

10/29/2026

🥳 Big news for our Seaside Vacations & Sales family!

Please join us in congratulating Lynn on being named the new Vice President of the Eastern Shore Association of Realtors!!!! In other ESAR news, Lance, will continue to serve in his role as the Treasurer after past duties as the President and Vice President himself! And, Elaine, who has served on the Chincoteague Chamber of Commerce’s BOD for almost 10 years, plans to continue to do so for another 3 years.

We're SO proud of all of them for always dedicating their time, experience, and leadership to helping to strengthen this amazing area we call home. Their commitment reflects something that truly means the world to the Seaside team: making a positive impact on the Eastern Shore.

Congratulations Lynn, Lance, and Elaine! Thank you for always representing Team Seaside and always doing your part to make the Shore an even better place to live, work, and play!

10/28/2026

Sometimes, you just need a quick reset.
A little salt air. A moment to yourself.

Let the waves be louder than your To-Do List.

https://www.seasidevacations.rentals/

10/26/2026

Introducing Wonderview 108, also known as Channel Retreat!

Please join us in welcoming one of the latest additions to our Seaside Vacations family! Located on the east side of Chincoteague Island, this first-floor condo is a nature lover’s paradise.

Start your mornings on the waterfront balcony, watching eagles, herons, and egrets fish for their morning meal. Grab your binoculars, and you might even spot wild ponies grazing across the channel!

Guests can also fish and crab right from the backyard, then head inside to turn the day’s catch into a fresh seafood dinner! 🦀

Perfect for a small family getaway or an escape for two, this cozy condo is a welcoming place to unwind after a day of exploring the island.

Click the link to see more of Channel Retreat, or give our team a call at (757) 336-7070 for more information!

https://www.seasidevacations.rentals/rentals/wonderview-108-channel-retreat

10/24/2026

🎃🍂 Team Seaside is officially PUMPKIN TOUR READY! 🍂🎃

Thanks to the AMAZING creativity and hard work of our very own Beritt, we’re all set for this year’s Pumpkin Tour! 🎨👏

Be sure to stop by the trail on Hallie Whealton Smith Drive and check out her incredible work, and don’t forget to explore all of the other amazing pumpkin creations from local students and businesses throughout our community!

We love seeing our community come together for fun traditions like this, and we can’t wait to see everyone’s creativity on display!

10/23/2026

We’ll take the hit(s), you enjoy the savings! Come visit Chincoteague Island this Fall and Winter and take advantage of amazing off season rates!

The same amazing beach town you love, with more money in your pocket.

10/22/2026

🏡 Chincoteague Island homeowners, let’s talk!

Choosing the right team to care for your home is a BIG decision. At Seaside Vacations & Sales, we understand how much your investment means to you, and how important it is to know it’s being looked after with care and attention.

Our award-winning team would love to chat about how we can help maximize your rental revenue, care for your property, and ease the day-to-day responsibilities of managing a vacation rental. You deserve to enjoy the rewards of homeownership with confidence that a dedicated team is looking out for you and your home. ❤️

Whether you’re considering renting your property for the first time or are just exploring the possibility of a change, we’d love to hear about your goals, answer your questions, and share how Seaside can help. With the changing times and uncertainty in the vacation rental market, having a team dedicated to representing you and your property can make a world of difference.

The tides may change. Our commitment doesn't. ❤️

Let’s start a conversation about your home’s potential, and the peace of mind that comes with being part of the Seaside Family!

Interested in having a chat? Give our team a call at (757) 336-7070 or reach our owners at [email protected] or [email protected].

We can't wait to meet you! 😄

10/20/2026

It’s ! 🎣💙

A big THANK YOU to Vinton for choosing Seaside Vacations for his fishing trip to the island! There’s nothing quite like trading the everyday routine for some time on the water, and we’re so glad we could be part of your island getaway!

After a day spent casting lines, having a comfortable place to kick back and relax makes the trip even sweeter (especially when you have a screened in porch to soak in the island breezes on!) Thank you for making Seaside your home away from home, Vinton!

We hope your next fishing adventure brings you right back our way. Until then, tight lines! 🐟🌊

https://www.seasidevacations.rentals/rentals/les-bon-temps

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

https://www.seasidevacations.rentals/

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