Seaside Vacations & Sales Chincoteague Island

Seaside Vacations & Sales Chincoteague Island 🏆Voted Best of Locals Choice 2022, 2023, & 2024!
🏆VRMA's 2023 Vacation Rental Management Co. We Live here, we work here, we play here.

of the Year
🏆VRMA's 2024 Excellence Award for Community Impact
🏆Vintory's Market Leader Award!

❤️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 ⭐"Even nicer than pictured" — now that's what we love to hear! 😍Jennifer and her family had the sw...
06/24/2025

⭐ Testimonial Tuesday ⭐

"Even nicer than pictured" — now that's what we love to hear! 😍
Jennifer and her family had the sweetest stay at Pony Paradise, complete with great beachy decor, prompt communication, and even a few pony visits across the street 🐴

We’re so glad you had a wonderful experience — and we’d love to welcome you back anytime!

📍 Pony Paradise
📆 Book your own stay: https://www.seasidevacations.rentals/rentals/pony-paradise



🥳Happy Work Anniversary to Bre & Lester! Today, the Seaside family is celebrating not one, but TWO amazing members of ou...
06/23/2025

🥳Happy Work Anniversary to Bre & Lester!

Today, the Seaside family is celebrating not one, but TWO amazing members of our family who've made a lasting impact here at Seaside Vacations!

Today marks Bre's 5th year with Seaside in our Operations department! Bre's commitment to excellence have been instrumental in keeping things run smoothly, and we've LOVED seeing her grow into her new role with us! We're so lucky to have her!

Lester is celebrating two years as a member of our Laundry team! His hard work, attention to detail, and reliability help ensure that ALL of our guests have everything they need for a comfortable stay, and if you've met Lester, you know his personality and positivity are contagious!

THANK YOU Bre and Lester for your all of the incredible work you do every single day. Seaside wouldn't be the same without you!


🎥✨ We’re back with a brand new episode of Live Like A Local! ✨🎥In episode 6, we had the pleasure of sitting down with Br...
06/23/2025

🎥✨ We’re back with a brand new episode of Live Like A Local! ✨🎥

In episode 6, we had the pleasure of sitting down with Britney, one of the amazing owners of Adams Auto Repair, right here on Chincoteague Island! 🛠️🚗

In this heartfelt and inspiring episode, Britney shares:
👫 What it’s like to run a business with her spouse
🏝️ What raising a family on the island means to her
🍽️ And their favorite places to eat, relax, and enjoy the magic of Chincoteague

Whether you’re a local, a longtime visitor, or dreaming of your first trip — you won’t want to miss this peek into island life through Britney’s eyes.

📺 Watch Episode 6 of Live Like A Local at the link below, and be sure to subscribe to follow along as we share more stories from locals across the island!

🔗: https://youtu.be/C3D_tHXdi6Y

06/23/2025

Another Sunday sunset… and another reminder that we live in the most magical place on earth. 🌅✨

Chincoteague, you never fail to take our breath away. 💛



06/21/2025

You never know what’s gonna happen on this crazy island! Surfer Dude’s Grandson made a visit to the Seaside office today! 🏄🏼🌴

That’s right — one of the most iconic bloodlines in Chincoteague Pony history stopped by to say hello 🐴✨ He’s just as charming as his granddad, and we were thrilled to have him hoofin’ around the office for a bit.

Only on Chincoteague, right?



06/21/2025

Have you ever heard of a McDonald’s…
with wild ponies in the parking lot? 🐴🍟

Only on Chincoteague Island.
Right on Maddox Boulevard, just on your way to the beach — you’ll spot visitors and guests feeding ponies and making a new friend ♥️

It doesn’t get more Chincoteague than that!!

Thanks to the Refuge Inn for housing these ponies for so many years and making memories for generations!



06/20/2025

☀️ It’s the first day of summer! ☀️

We couldn’t be more excited for sunshine, good vibes, and the start of an unforgettable season 🌊

Even better — this is Bobbi’s Seaside video debut, and she absolutely killed it! 😎🎥

Haven’t booked your summer stay yet? There’s still time! Explore our Chincoteague rentals at https://www.seasidevacations.rentals/chincoteague/rentals 🏡



🌟 Happy Juneteenth! 🌟Today, we want to take a moment to honor freedom, resilience, and the ongoing journey toward equity...
06/19/2025

🌟 Happy Juneteenth! 🌟

Today, we want to take a moment to honor freedom, resilience, and the ongoing journey toward equity and justice. Juneteenth is a reminder to us all of the power of community, the strength in unity, and the importance of remembering our shared history.

At Seaside Vacations & Sales, we’re proud to celebrate this day of reflection, joy, and cultural significance. May we all continue to learn, grow, and stand together in support of a brighter, more inclusive future.

https://www.seasidevacations.rentals/chincoteague/rentals



🚨 WE'RE HIRING in Pocomoke, MD! 🚨Seaside Vacations & Sales is growing — and we want YOU on our team! 🏖️👕 Now hiring: Exp...
06/18/2025

🚨 WE'RE HIRING in Pocomoke, MD! 🚨
Seaside Vacations & Sales is growing — and we want YOU on our team! 🏖️

👕 Now hiring: Experienced Laundry Folders - Night Shift & Weekend Shift
📦 Also hiring: Laundry Truck Driver (Clean driving record required)

✅ Hotel or commercial laundry experience preferred for Folders
✅ Driver must be reliable & able to lift up to 50 lbs
✅ Serving our properties in Chincoteague & Ocean City, MD
✅ Work at our professional laundry facility in Pocomoke, MD

💼 Competitive pay
⏰ Flexible shifts
🙌 Friendly, fast-paced work environment

📩 APPLY TODAY
DM us or email us at [email protected]
Join our team and help deliver 5-star vacation experiences! 🌟

🌊✨ Big News from Assateague Inn 208! ✨🌊Looking for the perfect quick escape to Chincoteague Island? Say hello to the new...
06/18/2025

🌊✨ Big News from Assateague Inn 208! ✨🌊

Looking for the perfect quick escape to Chincoteague Island? Say hello to the newly updated Assateague Inn 208 — a cozy one-bedroom suite that’s just right for your next getaway! 🏖️🛏️

The owners have been busy all off-season making incredible upgrades — and we’re beyond excited to finally share them with you! From refreshed interiors to thoughtful touches throughout, this space is made for relaxing after a day of island adventures. 🐚☀️

PLUS… the brand new pool deck is almost ready, just in time for summer! 🏊

Whether you’re planning a spontaneous weekend or a sunny week away, NOW is the time to book your stay and experience the best of island life. Hit the link below to see more of the updates and rates, or give our team a call at (757) 336-7070! ☎️

https://www.seasidevacations.rentals/rentals/assateague-inn-208s

🌞 Happy National Picnic Day! 🧺What better way to celebrate than with a picnic by the beach — and lucky for you, Chincote...
06/18/2025

🌞 Happy National Picnic Day! 🧺

What better way to celebrate than with a picnic by the beach — and lucky for you, Chincoteague has plenty of new food spots perfect for just that!

From sandwiches and seafood to savory bites you can grab and go, we’ve rounded up all the fresh flavors new to the island this summer.

🍽️ Check out our latest blog post to see what’s cooking:
👉 https://www.seasidevacations.rentals/blog/fresh-flavors---new-food-spots-to-try-on-chincoteague-island-this-summer



🚨 Just Released: Coastal Retreat is now OPEN for the week of July 5th — and this one’s a gem! 🚤This waterfront stunner s...
06/17/2025

🚨 Just Released: Coastal Retreat is now OPEN for the week of July 5th — and this one’s a gem! 🚤

This waterfront stunner sleeps 8 and has 3 bedrooms plus a loft, a private floating dock, and views that will take your breath away. It’s full of charm, sunshine, and space to truly unwind. 🌅

Even better? Your pup can come along — no extra fee! 🐶💙

Located right on the Assateague Channel, it’s the perfect launch point for a boat day, a seafood night, or just soaking in that salty breeze from the deck.

Don’t miss your chance to spend Independence Week at Coastal Retreat —
👉 https://www.seasidevacations.rentals/rentals/coastal-retreat



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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We Live Here, We Work Here, We Play Here!

Seaside Vacations is a full service Vacation Rental & Property Management Company located on beautiful Chincoteague Island on the ESVA. As Fully Licensed Real Estate Professionals, we can help you with any and ALL of your Real Estate Needs!

We, Lance and Elaine Stitcher, founded Seaside Vacations with the belief that there is a better way to vacation in Chincoteague Island, Virginia and Ocean City, Maryland. As a working family with two teenage boys and two beach Boxers, we understand how difficult it can be to get away and how precious that time together is. Our personal service, attention to detail, and providing a good product consistently are the building blocks of our great Vacation Relationships, whether they be with Partners or Guests. We want to make this vacation stress free for you - just sit back and enjoy the time with family and friends.

Together, we combine our love of the beach, the ocean and time with family to bring you a fantastically easy beach vacation. After our Guests needs are met, you’ll likely find us with our family boating, fishing and clamming on the local waters, or enjoying the occasional round of golf. You’ll often find us working on our Floating Office, “Escapade”at the Harbor in Robert Reed Park ~ stop by and say hello! We live here, We work here, We play here - Let us show you all the Eastern Shore has to offer - can’t wait to meet y’all! ~ Lance & Elaine Stitcher