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Find Trusted Child Care Providers Near Me in Chestertown, MD

We have 24 child care providers in Chestertown, MD! Compare and hire the best child care to fit your needs.

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Find childcare providers in Chestertown:

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Sara S.'s Photo

Sara S.

Creative And Experienced Sitter

Chestertown, MD

5.0(1)
from
$20/hr
4 years experience·
Hired by 3 families in your area
Light cleaning
carpooling
craft assistance
swimming supervision
grocery shopping
+ 1 more
I have 4 years of sitter experience with ages ranging between 4 months and 10 years, and daycare experience at the infant age level. With a loving and creative personality, I am sure to create a unique, safe, and fun environment for the family I work with. As the oldest of six siblings, caring for others and kids especially is a...

Elli F. says "Sara nannied for my infant daughter for 6 months and she was fantastic!! If you need a babysitter/nanny look no further. She is super knowledgeable about...

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Shelby F.'s Photo

About Me!

Chestertown, MD

5.0(1)
from
$20/hr
5 years experience
I have been working with children since 12 years old, starting with watching relatives and family friends, and eventually working for a service. I am currently in school at Washington College, studying to be a teacher. I have experience with children ages 6 months to 14 years old, however my favorite ages are under 1 and...

Kelly D. says "Shelby was absolutely amazing with our Cane Corso. He is incredibly sweet and loves people; however, he looks intimidating. There is always a bit of...

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Victoria A.'s Photo

Fun Babysitter Or Petsitter!

Chestertown, MD

from
$15/hr
3 years experience·
Hired by 1 families in your area
Grocery shopping
light cleaning
swimming supervision
I have 5 years of experience working as a camp counselor/life guard/swim teacher. I can help with Light Housekeeping and Grocery Shopping. I am studying environmental science and education at school and I love working with kids! I'd be happy to help with homework, play outside, go for walks or hikes, and do arts and crafts...
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Brooke F.'s Photo

Chestertown, MD

from
$15/hr
4 years experience·
Hired by 1 families in your area
Light cleaning
carpooling
craft assistance
swimming supervision
grocery shopping
+ 1 more
Hi parents/guardians! I am a well-experienced babysitter/nanny that is hoping to expand myself in my college town. I am a senior at East Carolina University pursuing a degree in marketing. I am available for a long-term position as a nanny and also as an occasional babysitter. I commonly complete light house-keeping while...
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Tiffany D.'s Photo

Awesome Personality, Trustworthy And Loyal!

Chestertown, MD

from
$20/hr
3 years experience
Meal prep
carpooling
grocery shopping
light cleaning
travel
I am a mother of two driven boys, one 20 attending Penn State and the other 17 still attending high school. I also am a substitute teacher, I have a passion for assisting in the development of our youth. I also worked in the medical field for many years serving and assisting sick patients. I obtain joy and fulfillment in serving...
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Veronica A.'s Photo

Fun & Safe Sitter!!

Chestertown, MD

from
$25/hr
3 years experience
Meal prep
carpooling
craft assistance
light cleaning
travel
Hello, my name is Veronica! I've been a nanny for three years and have had experience with ages of 3 months to 11 years old. I love making crafts and doing adventurous activities with the kids! I also do light housekeeping, homework help, and anything the family might need help with!
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Hannah B.'s Photo

Chestertown, MD

from
$20/hr
4 years experience
Light cleaning
carpooling
craft assistance
swimming supervision
grocery shopping
+ 1 more
I have over four years of experience providing attentive and dependable childcare. I enjoy creating a safe, supportive, and engaging environment for children, and I bring patience, kindness, and enthusiasm into my work every day. I am happy to assist with travel needs, age-appropriate crafts, and daily routines, always with the...
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Jennifer S.'s Photo

Nanny/ Caregiver/ Housekeeper

Chestertown, MD

from
$15/hr
10 years experience
Carpooling
craft assistance
swimming supervision
I am a loving, kind, patient and fun nanny. I have provided care for children from 3 to 12 years old. I am happy to provide transportation, assist with homework, housekeeping and pet care. Also, for the past 10 years I have been working for two agencies and privately as a Caregiver. During the past 17 years as a Park Ranger. I...
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Anna Maria B.'s Photo

Chestertown, MD

from
$15/hr
10 years experience·
Hired by 2 families in your area
Carpooling
travel
I'm a Caregiver for children and Seniors. I can assist you with your love one... I can be contacted at Four One Zero, Nine Zero Three, Eight Two Three Three. Thank you
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Maggie A.'s Photo

Fun Young Girl Who Loves Kids

Chestertown, MD

from
$17/hr
10 years experience
Grocery shopping
light cleaning
meal prep
Hello!! I am Maggie. I am 28 years old and love children. I have been watching children since I was 14 years old. I was a teacher for two years. I am looking for a part time nanny job where I can bring my 2-month-old son.
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Taylor H.'s Photo

Chestertown, MD

from
$18/hr
4 years experience
Bringing joy to children and peace of mind to families is my passion. For the past four years, I've had the pleasure of caring for children between the ages of 0 and 11. I'm comfortable caring for up to two children at a time. My experience in previous babysitting roles motivated me to continue making a positive impact on young...
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Susan S.'s Photo

Chestertown, MD

from
$15/hr
5 years experience
Light cleaning
swimming supervision
I'm a grandmotherly type of nanny, offering care for your infant child. I'm a semi-retired pianist who has taken time off from my accompanying jobs to care for infants throughout the years. I offer a patient, creative, and friendly approach to childcare. I have a college degree and am comfortable caring for one child at a time....
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Lauren S.'s Photo

Chestertown, MD

from
$20/hr
20 years experience
Meal prep
carpooling
grocery shopping
travel
light cleaning
+ 1 more
As a childcare provider with two decades of experience, I'm dedicated to nurturing children's growth and enriching their lives. My patient and friendly nature creates a welcoming environment for children to thrive. I value clear communication with parents, providing daily written reports and ensuring their preferred...
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Lucy S.'s Photo

Chestertown, MD

from
$15/hr
4 years experience
Meal prep
carpooling
grocery shopping
travel
light cleaning
+ 1 more
Bringing joy and nurturing care to children is my passion. With four years of experience, I offer families a reliable childcare option. My background includes some college coursework, along with First Aid Training and CPR Training. I'm patient, calm, friendly, and approachable. I provide regular updates through written reports,...
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Aliyah J.'s Photo

Chestertown, MD

from
$18/hr
4 years experience
Carpooling
grocery shopping
light cleaning
Bringing joy and nurturing care to children is my passion. For the past four years, I've dedicated myself to fostering the growth and development of children aged newborn to 11. My background in Early Childhood Education, along with First Aid and CPR Training, equips me to provide a safe and enriching environment. I am a...
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Child care centers in Chestertown, MD

Little Blessing Day Care

932 WASHINGTON AVE CHESTERTOWN, MD

5.0(3)

State license verified

starting at
$1/mo
Preschool
Day Care
Child care

Sally C. says "The teachers are knowledgeable, caring and understanding. When I pick up my daughter she does not wish to go home with me, which would make most moms sad...

See info
Preschool
Kindergarten
Child care
The Carrot Top Childcare and Learning Center provides an affordable childcare program in Chestertown, Maryland. They encourage the children's holistic growth through play-based and child-centered activities. They also aim to develop the children's social skills, emotional growth, and physical coordination. The Carrot Top...
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Academy Child Development Center

213 Fey Rd Chestertown, MD

Preschool
Kindergarten
Child care
Academy Child Development Center located in Chestertown MD offers a comprehensive early childhood program in a warm, caring, and friendly environment. It provides appropriate learning activities that stimulate growth among children. The center promotes balanced learning to make sure that children will develop emotionally,...
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Fairlee Manor Recreation & Education Center

22242 Bay Shore Rd Chestertown, MD

Camp Fairlee in the Fairlee Manor Recreation & Education Center in Chestertown, Maryland offers accessible camping experiences for children from six years old to adults. Camp Fairlee offers all the mainstream camp experiences to children and adults with various physical disabilities and cognitive impairments.Activities are...
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Kent School

Chestertown, MD Chestertown, MD

Preschool
Child care
Kent School is an independent school serving boys and girls from pre-kindergarten to 8th grade. Kent School's mission is to guide the students in realizing their potential for academic, artistic, athletic, and moral excellence. The school is family-oriented, supportive, and has a student-centered environment. They foster the...
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Showing 1 - 20 of 24

  • 24 child care providers are listed on Care.com

  • The average post rate is $17.87/hr as of January 2026

  • The average star rating for rated child care providers is 5.0

Recent child care reviews from local parents in Chestertown, MD

Child Care Providers in Chestertown, MD are rated 5.0 out of 5 stars based on 5 reviews of the 24 listed child care providers

Sara S.

Sara nannied for my infant daughter for 6 months and she was fantastic!! If you need a babysitter/nanny look no further. She is super...

- Elli F.

Shelby F.

Shelby was absolutely amazing with our Cane Corso. He is incredibly sweet and loves people; however, he looks intimidating. There is...

- Kelly D.

Little Blessing Day Care

The teachers are knowledgeable, caring and understanding. When I pick up my daughter she does not wish to go home with me, which would make...

- Sally C.

Common questions about child care in Chestertown, MD

Child care costs in Chestertown, MD can vary widely based on the type of care your family needs, your child’s age, and the schedule you’re looking for. Hourly rates often differ for nannies, babysitters, and other child care providers, with higher costs typically associated with infant care, multiple children, or full-time support. Many families start by estimating their budget with the Care.com child care cost calculator and then explore how rates compare across care types by reviewing average child care costs to better understand what to expect.

Families in Chestertown, MD can choose from several child care options based on their schedule, budget, and the level of consistency they need. Many families work with nannies who provide regular, in-home care and support daily routines, while others rely on babysitters for part-time, after-school, or occasional care. Some households may also consider live-in nannies, which can be a good fit for families who need extended coverage or more flexible hours. Additional options may include caregivers who help with school pick-ups, homework, meals, or bedtime routines. Understanding the full range of possibilities can make it easier to find the right fit, and a complete list of child care options can help families compare care types and responsibilities.

Finding reliable child care in Chestertown, MD often starts with clearly defining your family’s needs, such as schedule, budget, and the type of care that works best for your children. Many families compare caregiver experience, availability, and reviews from other parents before scheduling interviews or trial days. It can also help to divide the search and evaluation process between caregivers or partners, especially when juggling busy schedules, and some families take a more organized approach to finding child care together. Taking time to ask thoughtful questions, check references, and discuss expectations upfront can help ensure a dependable and long-term care match.

When choosing a child care provider in Chestertown, MD, it’s important to look for experience with your child’s age group, a caregiving style that aligns with your family’s values, and clear communication habits. Many families also consider reliability, flexibility with schedules, and how comfortable the provider is handling daily routines like meals, naps, and activities. Reviewing references, reading feedback from other families, and having open conversations about expectations can help you assess trust and fit. A provider who is attentive, consistent, and responsive can make a meaningful difference in your child’s day-to-day care.

When interviewing a child care provider in Chestertown, MD, focus on questions that help you understand how they would care for your child in real-life situations. Many families ask about experience with specific age groups, how a provider handles discipline, routines, and unexpected challenges, and what a typical day of care looks like. It’s also helpful to discuss communication preferences, reliability, and comfort with responsibilities like meals or transportation. Asking thoughtful babysitter interview questions and following proven tips for interviewing nannies can help you feel more confident as you compare candidates and move toward a hiring decision.

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