119 Babysitting Jobs Available in Chestertown, MD
Wyndy lists 119 babysitting jobs in Chestertown, MD posted by local families. Chestertown sitters on Wyndy earn an average of $23 per hour, or $92 plus tips per job. Families post after-school, date night, infant care and weekend jobs. Every job is open to background-checked college students and graduates, and every sitter is insured while working.
Earn: $23/hr avg + 100% of tips
Feel safe: Insured on every job
Be flexible: Pick jobs that fit your schedule
Recently posted babysitting jobs in Chestertown
Two elementary school boys near 21624 require a part-time sitter
Part-time sitter needed for two elementary school boys. Duties include supervision and engaging activities. Must have experience and positive attitude. Must be reliable and able to ...
Seeking babysitter in Chestertown, MD for infant twin care
Seeking babysitter in Chestertown, MD for infant twin care. Must have experience with infants and be reliable. Duties include feeding, diaper changing, and providing a nurturing ...
Looking for a recurring sitter in Chestertown, MD for occasional Fridays, date nights, and pet sitting!
Recurring sitter needed for occasional Fridays, date nights, and pet sitting. Must be reliable and experienced.
Seeking a nanny/babysitter in Chestertown to aid during remote work
Seeking nanny/babysitter to assist with remote work. Must provide care and supervision in Chestertown location. Must have experience and be reliable.
Seeking live-in or live-out newborn nanny/babysitter in Chestertown, MD
Seeking newborn nanny/babysitter for live-in/live-out position. Must have experience with infants. Willingness to help with feeding, changing, and nurturing. Light housekeeping may ...
Two boys in Chestertown, MD need a part-time sitter
Part-time sitter needed for two boys in Chestertown, MD. Must be reliable and attentive. Experience with kids preferred. Must pass background check. CPR and First Aid certification ...
Seeking a sitter in Chestertown for occasional Fridays, date nights, and pet care!
Occasional sitter needed for Fridays and date nights, also pet care! Ideal candidate will be reliable and experienced.
After-school help within Chestertown
After-school program seeking individual to provide assistance and support to students in Chestertown. Must have experience working with youth and possess strong communication ...
Before & after school care wanted in Chestertown, MD, no specific date
Before & after school care wanted in Chestertown, MD. Seeking an experienced individual to provide care and supervision for children during non-school hours. Must have a passion ...
Babysitting Jobs in Chestertown, MD: FAQs
How much do babysitters make in Chestertown, MD?
Parents set the pay for each job. Wyndy babysitters earn an average of $92 plus tips per job and keep 100% of their tips. Pay varies by job and is shown on each listing before you apply.
How do I get babysitting jobs in Chestertown, MD as a college student?
Apply to become a Wyndy babysitter, consent to a background check and complete your profile. Applications are reviewed for quality and you get an initial response within 48 hours. Once approved, express interest in babysitting jobs in Chestertown, MD in the Wyndy app and families send you offers.
What are the requirements to become a Wyndy babysitter?
You must be 18 or older, be enrolled in an accredited college or university or hold an undergraduate degree, have at least one year of childcare experience, have a driver's license, a Social Security number and reliable transportation, and consent to a background check.
How do Wyndy babysitting jobs work?
- Express interest in the jobs you like. You will see single-time, recurring and part-time babysitting jobs.
- Parents review the interested babysitters and send offers to one or more of them.
- Accept the offers you want to work and get paid for each job.
Every Wyndy babysitter is covered by insurance while working.
Are Wyndy babysitting jobs flexible for students?
Yes. You only express interest in the jobs that fit your schedule, so you can work around your class schedule during the semester and pick up more jobs over school breaks.


