Seaside Vacations & Sales Chincoteague Island

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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 🌟Tasha and her family had an amazing stay at The Virginia Lee — clean, cozy, and well-maintained, ...
19/08/2025

🌟 Testimonial Tuesday 🌟

Tasha and her family had an amazing stay at The Virginia Lee — clean, cozy, and well-maintained, with a super easy booking process. 💙 We love hearing how our guests make lasting memories here on Chincoteague!

Ready to plan your own getaway? Book The Virginia Lee today ➡️ https://www.seasidevacations.rentals/rentals/the-virginia-lee

18/08/2025

🦀✨ Life is good… but Island Life is better! ✨🦀

Welcome to The Salty Crab, a gorgeous home right in the heart of Chincoteague Island. Just steps from the Farmers Market, Historic Main Street, and Robert Reed Park’s famous sunsets, this 3-bedroom, 2.5-bath retreat is the perfect mix of coastal charm and comfort. 🌊☀️

Relax on the covered decks, gather around the fire pit, or bring the family dog along for the adventure — this home was made for memory-making. 🏡💙

Ready to plan your stay? Book The Salty Crab here 👉 https://www.seasidevacations.rentals/rentals/the-salty-crab

17/08/2025

Sundays are for slowing down 🌊✨

Join us for a peaceful walk through Waterman’s Memorial — a place where the island’s history, heritage, and spirit live on- and it is oh so peaceful 🤍

🎸🎶 FREE Concert in Robert Reed Park – August 16th! 🎶🎸Get ready for an evening of blues, soul, and high-energy fun! Join ...
16/08/2025

🎸🎶 FREE Concert in Robert Reed Park – August 16th! 🎶🎸

Get ready for an evening of blues, soul, and high-energy fun! Join Seaside Vacations & Sales and the Chincoteague Cultural Alliance this Friday at 6 PM in Robert Reed Park for a FREE live show featuring the Bobby BlackHat Band — Virginia’s own master of blues, bringing harmonica magic and smooth vocals to the stage.

This is a family-friendly event, so grab a chair or blanket, settle in by the water, and let the music carry you away.

Don’t miss this night of great vibes and unforgettable tunes! 🎤✨



15/08/2025

Happy National Relaxation Day! 🌿✨

Today’s the perfect excuse to treat yourself, and there’s no better place to do just that than one of our favorite local sanctuaries: Why Knot Massage, tucked in the Village Mall just off Main Street.

Whether you’re craving deep-tissue relief 💆‍♂️, a soothing hot-stone massage, a calming foot detox 🦶, or the healing energy of Reiki and craniosacral therapy, Laurie and Shannon have your back- literally. They masterfully blend traditional techniques with a holistic touch that nurtures your mind, body, and spirit.

Step into their peaceful upstairs studio, let the salt-kissed breeze fade, and emerge completely renewed, ready to take on more island adventures.

Life at the beach is always better when it includes a little intentional calm. 🧘‍♀️

Plan your bliss today—or grab that much-needed escape right now. Your body (and your spirit) will thank you 🩵🌊



💗🎣 Day 1 of the 2025 Poor Girls Open is officially underway in Ocean City, MD — and while the action kicks off today, ou...
14/08/2025

💗🎣 Day 1 of the 2025 Poor Girls Open is officially underway in Ocean City, MD — and while the action kicks off today, our big excitement starts tomorrow when one of our own hits the water!

Elaine — one of our amazing owners, a breast cancer survivor, and proud angler — made her tournament debut last year and landed her very first white marlin. 🐟💪 This year, she’s back and ready to fish for a cause that’s reeled in over $1.8 million for the American Cancer Society.

From Chincoteague to OC, we’re cheering her on every step (and cast) of the way. Go get ‘em, Elaine — we can’t wait to see what you bring in! 🌊💕

14/08/2025

Save this spot for your next Chincoteague getaway! 🏖️🍩

Sandy Pony Donuts isn’t just a quick morning stop—it’s a whole vibe. From hot, fresh donuts to refreshing açaí bowls, they’ve got the goods to fuel your island adventures. ✨🍓

Save it now, thank us later.



🎉 Happy Birthday, Lynn! 🎉Today we’re celebrating someone who wears multiple hats here at Seaside! Not only is Lynn one o...
13/08/2025

🎉 Happy Birthday, Lynn! 🎉

Today we’re celebrating someone who wears multiple hats here at Seaside! Not only is Lynn one of our amazing Realtors, but she’s also our caring and dedicated HR Manager! 💼🏡

Lynn, your sweet, kind, and giving soul makes such a difference in everything you do, and we are SO lucky to have you as part of the Seaside family. 💙 You make our days brighter, our team stronger, and our workplace warmer.

Here’s to you on your special day — may it be filled with all the love and joy you bring to others every day! 🥳


✨ Testimonial Tuesday ✨Home away from home? That’s exactly what Jeneene R. found at Casa Playa! 🏡🌊 From top-notch commun...
12/08/2025

✨ Testimonial Tuesday ✨

Home away from home? That’s exactly what Jeneene R. found at Casa Playa! 🏡🌊 From top-notch communication to unforgettable 4th of July fireworks, this stay had it all, and we couldn't be happier to hear it!

📣 “The check-in and communication was awesome… We will definitely be returning!”

Thank you, Jeneene, for the kind words — we love helping families make memories that last a lifetime 💙



12/08/2025

🐚 Brand new and beautifully designed, Sandpiper Shanty is coastal comfort with a touch of luxury — a spacious retreat that’s as perfect for family gatherings as it is for a peaceful escape.

Step inside to beachy hues, high-end finishes, and spaces made for making memories — from the dreamy chef’s kitchen to the screened porch where you can feel the island breeze. Less than 10 minutes from Assateague National Seashore, you’ll be close to wild ponies, pristine beaches, and endless adventures.

🛏 Sleeps 10 in 4 stylish bedrooms (including a fun bunk room)
🐾 Pet friendly — 2 well-trained dogs welcome
🔥 Cozy fireplace for off-season stays
📍 3625 Ridge Road, Chincoteague Island
✨ Be one of the first to experience Sandpiper Shanty — book now!
👉 https://www.seasidevacations.rentals/rentals/sandpiper-shanty



Happy National Play in the Sand Day! 🏖️✨Whether you’re building the ultimate sandcastle, hunting for seashells, or just ...
11/08/2025

Happy National Play in the Sand Day! 🏖️✨

Whether you’re building the ultimate sandcastle, hunting for seashells, or just enjoying that warm sand between your toes… today is the perfect excuse to get outside and enjoy our beautiful beaches! 🌊

What are you doing in the sand today?👇



Address

4101 Main Street
VA
23336

Opening Hours

Monday 09:00 - 17:00
Tuesday 09:00 - 17:00
Wednesday 09:00 - 17:00
Thursday 09:00 - 17:00
Friday 09:00 - 17:00
Saturday 09:00 - 17:00
Sunday 09:00 - 16:00

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