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

Find childcare providers in Chestertown:
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...
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...
Child care centers in Chestertown, MD
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...
601 High St Chestertown, MD
213 Fey Rd Chestertown, MD
22242 Bay Shore Rd Chestertown, MD
Chestertown, MD Chestertown, MD
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
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
- Elli F.
- Kelly D.
- Sally C.
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.