Virginia's Eastern Shore

OConnor Coastal

Home Management

Where nature, comfort,
and island life come together.

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Our Property

Pearl in the Pines

A coastal retreat on Chincoteague Island — book directly with us and skip the platform fees.

Chincoteague Island, Virginia

Pearl in the Pines

A charming coastal retreat nestled in the shade of tall pines in the private community of Oyster Bay — literally at nature's front door.

3 Bedrooms
2 Bathrooms
Up to 6 Guests
Kayaks & Bikes Included Washer & Dryer Screened Porch Fire Pit EV Charger Community Boat Launch Pet Friendly Linens Included
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Pearl in the Pines

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Pearl in the Pines · Chincoteague Island, Virginia

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Kevin and Sarah OConnor

Your Hosts

Hello, We're
Kevin & Sarah

Outdoor enthusiasts, devoted parents, and Eastern Shore transplants — we moved to the Delmarva Peninsula to share our home and our deep love of nature with you.

Kevin brings an engineer's eye for detail and over 30 years of local knowledge to every stay. Sarah spent her career as an epidemiologist before stepping away to raise their family — she brings that same dedication to cleanliness, care, and guest well-being to every stay we host. Together, our adventures and travels shape every visit to Pearl in the Pines.

Get in Touch

Local Knowledge

30+ years exploring Chincoteague Island

Fun Fact — Kevin

Has rock climbed El Capitan in Yosemite

Fun Fact — Sarah

Was a pole vaulter on her track team

Based In

Salisbury, Maryland

We Always

Share everything we know about the island

We're Obsessed With

Finding peace amidst life's journey

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Let's Plan
Your Stay

Skip the platform fees and book directly with us. Fill out the form and we'll get back to you promptly with confirmation and rates.

📬 We typically respond within a few hours. Once we confirm availability, we'll send you everything you need to finalize your booking.

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