Chesapeake Cottage Assisted Living - welcoming exterior with porch and landscaping in Snow Hill, Maryland
Family-Owned Senior Care on Maryland's Eastern Shore

A Home, Not a Facility

Where every resident is known by name, cared for like family, and treated with the dignity they deserve.

Family-Owned & Operated
24/7 Personalized Care
Starting at $4,000/mo
Licensed in Maryland

Built by a Family, for Your Family

The Underwood Family

In 2016, we purchased Chesapeake Cottage and redesigned it from the ground up — creating the kind of warm, personal senior care home we'd want for our own family. Every detail was curated with our residents in mind.

Meet Our Family →

What Families Are Saying

"Trust me, this is the place if you're looking! I was blown away by the quality of care and kindness by the staff."

— Rose Darline Dorcius

"A loving home for their residents. Always caring, professional and accepting. I couldn't have picked a better place for my Aunt."

— Crystal Judd

"The kindest group of folks I have met. Their small family atmosphere is perfect. Seth truly cares about both residents and their family."

— Mary Rufenacht

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Everything Your Loved One Needs, All Under One Roof

Personal Care & Daily Assistance

Compassionate help with bathing, dressing, grooming, and everyday tasks -- always with dignity and respect.

Medication Management

Careful, accurate medication administration and monitoring by trained staff, every single day.

Home-Cooked Meals & Nutrition

Nutritious, delicious meals prepared fresh daily in our home kitchen, with dietary needs always accommodated.

Activities & Social Engagement

Meaningful daily activities, outings, and social programs tailored to each resident's interests and abilities.

Dementia & Memory Support

Specialized, patient care for residents with Alzheimer's and other forms of dementia in a safe, familiar setting.

24/7 Supervision & Safety

Round-the-clock staffing so you can rest easy knowing your loved one is always safe and never alone.

Why Families Choose Chesapeake Cottage

Small by Design

Only a handful of residents means more one-on-one attention, deeper connections, and care that's truly personal.

A Real Home, Not a Facility

A kitchen, a living room, rocking chairs on the porch. No long hallways or room numbers — just a warm, comfortable home.

Your Family Becomes Our Family

Same caregivers every day who know your loved one by name — their stories, their preferences, and what makes them smile.

Hands-On Owner Involvement

We're not a corporation — Seth and Brittany are personally involved in the care of every resident and always just a phone call away.

Home-Cooked Meals, Always

Real food made fresh in our kitchen — not institutional cafeteria trays. Dietary needs always accommodated.

Peaceful Country Setting

Located on a quiet road in Snow Hill, surrounded by nature — a safe, calm environment away from the noise of the city.

Transparent, All-Inclusive Pricing

One monthly rate covers everything — meals, medication management, personal care, activities, and more. No surprise fees.

We Help You Navigate Paying for Care

Private pay, VA benefits, long-term care insurance, Medicaid — we'll help your family explore every option available.

See If Chesapeake Cottage Is Right for Your Family