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!

"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. ❤️🌅🎶

09/06/2026

🎶🥁 Tonight's the night! 🥁🎶

We can't wait to see everyone at Robert Reed Waterfront Park this evening as we send off another incredible summer season with one final FREE family concert!

Get there early to grab a great spot and soak in the beautiful waterfront views (Can you imagine these views with the sunset right behind the stage?!) before C.A.I.S.O. takes the stage at 6 PM with their infectious blend of Calypso, Reggae, and Latin Jazz. 🌴🥁

Bring your lawn chairs or blankets, gather your family and friends, and don't forget your dancing shoes—this is always one of the most fun nights of the summer!

We'll see you at the park! 🌅💃🕺

🍕🌮🍔🦀 It’s lunchtime on Chincoteague… and the Seaside team has one VERY important decision to make:What are we eating tod...
09/03/2026

🍕🌮🍔🦀 It’s lunchtime on Chincoteague… and the Seaside team has one VERY important decision to make:

What are we eating today?! 🤔

Pizza? 🍕
Tacos? 🌮
Fresh local seafood? 🦀
A big, juicy burger? 🍔
Head to Island Foods and make our own lunch? 🥪
Or maybe we hit one of the island’s food trucks? 👀

With so many incredible places to grab a bite around Chincoteague, we honestly feel a little spoiled sometimes! 😋

So, help us settle the lunch debate! What’s one of YOUR favorite spots or go-to lunch orders on the island?

Drop your recommendations below! 👇 We may just let the comments decide where we’re headed today!

Summer may be winding down, but we’re not letting it go without one last party at Robert Reed Downtown Waterfront Park! ...
09/02/2026

Summer may be winding down, but we’re not letting it go without one last party at Robert Reed Downtown Waterfront Park! 🎉

Join Seaside Vacations and the Chincoteague Cultural Alliance this Sunday, September 6th at 6 PM, for our FINAL FREE CONCERT of the summer as C.A.I.S.O. returns to Chincoteague! 🙌

One of the hottest steel drum bands in the DC and Baltimore area, C.A.I.S.O. brings an incredible mix of Calypso, Reggae, and Latin Jazz influences that turns the park into an island party! 🌴🥁🎶

If you’ve joined us for C.A.I.S.O. before, you already know that this is one of the MOST FUN concerts of the year!

🪑 Bring a lawn chair or blanket
💃 Definitely bring your dancing shoes
🌅 Find a spot along the waterfront
🎶 And help us send summer off with a BANG!

There’s no better way to close out another amazing summer on Chincoteague than dancing with friends and family as the music plays and the sun goes down over the water. 💙

We'll see you in the park!

💫Testimonial Tuesday 💫Sometimes the best vacation rentals are the ones that make it easy to settle in, get comfortable, ...
09/01/2026

💫Testimonial Tuesday 💫

Sometimes the best vacation rentals are the ones that make it easy to settle in, get comfortable, and feel right at home! 🏡❤️

A big thank you to Orasa for choosing Seaside Vacations and Little Red Cottage for their island getaway! As a family that loves to cook, having a place where they could prepare and enjoy their favorite meals together was important, and Little Red delivered! There's nothing like sharing family recipes, including some fresh, local ingredients, and creating memories at your home away from home!

Thanks again for choosing to stay with us Orasa! We're so happy this home gave your family all of the comforts you needed, and we hope to have you all back soon!

https://www.seasidevacations.rentals/rentals/little-red-cottage

☀️🌊 ONE WEEK TO GO! 🌊☀️We’re just ONE WEEK away from the unofficial last weekend of summer! 🥹🏖️Labor Day is almost here,...
08/31/2026

☀️🌊 ONE WEEK TO GO! 🌊☀️

We’re just ONE WEEK away from the unofficial last weekend of summer! 🥹🏖️

Labor Day is almost here, which means there’s still time for one more weekend of salty air, sandy toes, and making memories in your favorite beach town before summer fades away.

🌊 Hit the waves one more time
☀️ Soak up every last bit of summer sunshine
🏖️ Spend the day with your toes in the sand
🛶 Get out on the water for one more adventure
🍤 Visit your favorite local restaurants
🌅 And end the day with a beautiful coastal sunset

Summer isn’t over JUST yet, so let’s make these last days count! Click the link below to check availability for the holiday weekend, or give our team a call at (757) 336-7070 and let our team find the perfect match for your family getaway!

https://www.seasidevacations.rentals/

One of your favorite Chincoteague homes is getting even better — Hudson House will officially be PET FRIENDLY in 2027! 🐶...
08/29/2026

One of your favorite Chincoteague homes is getting even better — Hudson House will officially be PET FRIENDLY in 2027! 🐶🎉

Hudson House has been a favorite for families for years, and now your furry family members can join in on the island adventures, too! 🐾🌊

There’s so much to love about this beautiful island getaway:

📍 Just steps from Historic Downtown Main Street & the Farmers Market
🛏️ 4 Bedrooms
🛁 3 Bathrooms
🌿 A relaxing screened-in porch
🔥 A backyard firepit perfect for gathering together after a day of island adventures

From mornings strolling downtown to evenings around the fire sharing stories, roasting marshmallows, and making memories, Hudson House has everything you need for an unforgettable Chincoteague getaway — and in 2027, no family member has to stay behind! 🐕💙

Click the link below to see more of Hudson House, or give our team a call at (757) 336-7070 so our team can help you start planning your next island getaway!

🏠: https://www.seasidevacations.rentals/rentals/hudson-house

08/28/2026

🌊☀️ FINALLY FRIDAY! ☀️🌊

The weekend is here, and Chincoteague is calling! 😎

With beautiful weather on tap, this is the kind of weekend made for getting outside and exploring everything our little island has to offer by land AND by water!

Summer may be winding down, but weekends like this remind us that some of the BEST days on Chincoteague are still ahead. 💙

So get outside, explore somewhere new, and make the most of your weekend in your happy place!

https://www.seasidevacations.rentals/

🎶 IF YOU'RE READING THIS, YOU'RE INVITED! 🎶Seaside Vacations is proud to co-sponsor another FREE family concert this Sat...
08/27/2026

🎶 IF YOU'RE READING THIS, YOU'RE INVITED! 🎶

Seaside Vacations is proud to co-sponsor another FREE family concert this Saturday, August 29th, featuring the Bobby BlackHat Band!

Get ready for an incredible blues experience that’ll have the entire crowd tapping their toes, moving to the music, and dancing the night away! 💃🕺

👨‍👩‍👧‍👦 Perfect for the young AND the young at heart, all you'll need to enjoy the concert is a lawn chair or blanket 🪑, your favorite refresher 🥤, and some shoes you'll be comfortable dancing in if the music moves you!

Grab the family, find your spot in the park, and join us for an evening of great music, beautiful waterfront views, and the kind of summer memories that make Chincoteague so special. 🥰

We’ll see you at Robert Reed Park this Saturday at 6 PM!

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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