Sittercity home

Find a Babysitting Job in Chestertown, MD

Search for jobs, message families, and build a career you love—all for free

18 Babysitting Jobs Found

  • $23–29/hr
  • Annapolis, MD • 25 miles away

Help Needed to Supervise and Engage One...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We want a friendly babysitter for our preschool child. This position involves supervising playtime and ensuring safety both indoors and outdoors. You will prepare simple snacks and help with basic learning activities. The job starts on December 22, 2025, but we can adjust the start date if needed.... More

  • $19–22/hr
  • Baltimore, MD • 22 miles away

Driver for school drop off, high school...

  • 1 child
  • Babysitting
  • M
  • T
  • W
  • T
  • F

Weekly

7:00am - 8:00am

Hi! We need someone to provide morning transportation for our teen daughter starting December 5, 2025. You will work Monday through Friday (school year schedule), arriving between 7:00-7:15 AM and dropping off at school approximately 20 min away from our home, the pickup location. Both locations are... More

  • $10–20/hr
  • Edgewood, MD • 18 miles away

Looking for a sitter for 2 toddlers 4-6 PM

  • 2 children
  • Babysitting
  • M
  • T
  • W
  • T
  • F

Weekly

12:00am - 2:00am

Hi! We need someone to watch our two young children, a 1year 9months old and a 3 year old, from December 3, 2025, Monday through Friday, from 4:00 PM to 6:00 PM. Your responsibilities include supervising playtime, preparing snacks, and helping with activities that keep them engaged. You must have a... More

  • $21–22/hr
  • Middle River, MD • 18 miles away

Seeking Reliable Babysitter with Car for...

  • 1 child
  • Babysitting
  • M
  • T
  • T

Weekly

7:30am - 9:30am

Hi! I'm looking for a babysitter to watch my elementary school child on Mondays, Tuesdays, and Thursdays from 7:30 AM to 9:00 AM, starting December 8, 2025. The role involves preparing breakfast, helping with morning routines, and ensuring safety on the way to school. A reliable car is a must for a... More

  • $20–24/hr
  • Perry Point, MD • 24 miles away

Experienced Babysitter Needed for Two...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

I’m looking for a fun and caring babysitter for my two preschool boys starting December 1, 2025, at 9:30 AM until 3 PM. They’re active and curious, so I need someone who can keep up with them, engage them in games and activities, and help guide them when needed.

I’ll be working from home in... More

  • $15–25/hr
  • Baltimore, MD • 22 miles away

Seeking Responsible Babysitter with car

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hello! We want a babysitter for our preschool-aged child. The job starts on December 1, 2025.

You will play with our child, help with meals, and keep things tidy. Reading stories and encouraging creativity are important parts of the day.

You need to have a car for outings and to transport our... More

  • $20–24/hr
  • Baltimore, MD • 23 miles away

Babysitter Needed for One Elementary Child...

  • 1 child
  • Babysitting
  • S
  • T
  • F
  • S

Weekly

7:00am - 9:00am (flexible)

We are looking for a reliable babysitter for our elementary-aged child. The start date is flexible, with shifts from 7:00 AM to 8:30 AM on Saturdays, Sundays, Thursdays, and Fridays beginning January 1, 2026. The sitter must have their own car and be comfortable with pets. Your primary... More

  • $20–24/hr
  • Baltimore, MD • 23 miles away

Seeking Experienced Sitter with Car for...

  • 3 children
  • Babysitting

Occasional

On an as-needed basis

We are seeking a responsible babysitter to care for three children, including two preschoolers and an infant. The sitter should have experience with multiples and must have their own car for transportation. The job will start on November 17, 2025, but the start date is flexible. Your primary duties... More

  • $18–20/hr
  • Dundalk, MD • 20 miles away

Babysitter Needed for Toddler Starting...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hello, we need a babysitter for our toddler starting November 17, 2025. You will look after one child during our time away. Your tasks include engaging in playtime, preparing snacks, and ensuring safety during activities. It is important to have a car for transporting our child to fun outings or... More

  • $20–24/hr
  • Nottingham, MD • 23 miles away

Flexible Babysitter Needed for Two...

  • 2 children
  • Babysitting
  • T
  • W
  • F

Weekly

12:00am - 3:00am (flexible)

We need a reliable babysitter for two children, a preschooler and an infant. The schedule starts on November 17, 2025, at 10:30 PM, with flexibility. Regular care will be needed on Tuesdays, Wednesdays, and Fridays from 3:30 PM to 6:00 PM. The sitter must have their own car to transport the children... More

  • $21–25/hr
  • Baltimore, MD • 24 miles away

Babysitter needed for infant babygirl?Car...

  • 1 child
  • Babysitting
  • M
  • T
  • W
  • T
  • F

Weekly

6:00am - 5:00pm

Hello Future Nanny to our adorable babygirl. My Husband and I are looking for a nanny to care for our 9 month daughter Khelani'Marie. Our daughter is definitely a baby who needs her sitters undivided attention. So the job starts when your hired and we need a sitter who can care for our daughter from... More

  • $21–25/hr
  • Arnold, MD • 22 miles away

Reliable sitter needed for two infants on...

  • 2 children
  • Babysitting
  • S

Weekly

8:30am - 5:30pm

Hi! We’re looking for a babysitter for two young children, including an infant. The position starts on November 13, 2025, and will take place every Saturday from 8:30 AM to 5:30 PM.

Your main tasks will include supervising playtime, feeding, changing diapers, and putting the infant down for naps.... More

  • $16–22/hr
  • Dundalk, MD • 20 miles away

Babysitter Needed for 2 Kids, Flexible...

  • 2 children
  • Babysitting
  • T
  • W
  • T
  • F
  • S

Weekly

2:30pm - 11:30pm (flexible)

We want a responsible babysitter to support our family. The position starts on December ninth, 2025, with flexible scheduling. The hours are from 2:30 PM to 11:00 PM, Tuesday through Saturday. You will watch over two children, one toddler and one in middle school. Reliable transportation is... More

  • $20–24/hr
  • Bel Air, MD • 24 miles away

Seeking Babysitter for Preschool Child,...

  • 1 child
  • Babysitting
  • M
  • T
  • W
  • T
  • F

Weekly

12:00am - 6:00am (flexible)

Hello! We need a reliable babysitter for our preschool child. The job starts on November 10, 2025, from 12:00 PM to 5:30 PM, Monday through Friday. You must have a car to transport our child if needed. Your tasks include supervising activities, preparing snacks and meals, and playing games. It’s... More

Babysitting FAQ

Jump to Top

Today only! Save up to 50% on a
Sittercity Premium membership.

Register now