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Find a Babysitting Job in Chestertown, MD

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25 Babysitting Jobs Found

  • $21–22/hr
  • Glen Burnie, MD • 24 miles away

Needing a babysitter for two children for...

  • 2 children
  • Babysitting
  • S
  • M

One-time

Start date: 02/15 - 02/16

9:00pm - 1:00am (flexible)

Hello Sitters,

We are looking for a reliable sitter to help care for our two children—our daughter Adrianna (4) and our son Eli (8). Eli is level 2 autistic as well. They are both very lovable, easygoing, and fairly independent kids.

We do have two pets in our home. They do not require help while... More

  • $22–26/hr
  • Baltimore, MD • 22 miles away

Babysitter needed for one elementary...

  • 1 child
  • Babysitting
  • S

Weekly

4:30pm - 7:30pm

Hello sitters! We’re looking for a reliable babysitter for our elementary-aged child. The role starts on February 15th and runs every Sunday from 4:30 PM to 7:30 PM.

Responsibilities include supervising playtime, helping with homework, and preparing a simple meal or snack. You’ll engage our child... More

  • $22–26/hr
  • Annapolis, MD • 25 miles away

Babysitter needed for one preschool child ...

  • 1 child
  • Babysitting
  • T

One-time

Start date: 03/12

12:30pm - 5:30pm

Hi, we are looking for a babysitter to support our child from March 12th. The hours are from 12:30 PM to 5:00 PM. The child does not have special needs but enjoys sensory activities.

You will supervise our preschool child, engage them in fun activities, and possibly feed him snacks. Your experience... More

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

Seeking Caring Babysitter for Toddler on...

  • 1 child
  • Babysitting
  • F

One-time

Start date: 05/01

5:30pm - 10:30pm (flexible)

We are looking for a responsible and caring babysitter to watch our toddler on May 1, 2026, from 5:30 PM to 10:30 PM, with a flexible start time. Your main duties will include ensuring the child's safety, engaging in age-appropriate activities, preparing light snacks, and following the child’s... More

  • $19–26/hr
  • Baltimore, MD • 22 miles away

Babysitter needed for 3YO boy on February...

  • 1 child
  • Babysitting
  • S

One-time

Start date: 02/14

4:30pm - 11:30pm

Hi! We need a babysitter for our preschool-aged child starting February 14th. The hours are from 4:30 PM to 11:30 PM. You will supervise and engage our child with fun activities, including games and reading.

Cooking a simple meal is part of the job. You will also handle bedtime routines and ensure... More

  • $18–28/hr
  • Bel Air, MD • 24 miles away

Looking for a reliable babysitter for a...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We need a babysitter for our toddler starting on or after February 10, 2026. The schedule is flexible. You will be responsible for providing care, engaging in activities, and ensuring a safe environment. The sitter must have their own car for transportation. Experience with toddlers is preferred.

  • $22–26/hr
  • Middle River, MD • 18 miles away

Babysitter needed for three kids, starting...

  • 3 children
  • Babysitting

Occasional

On an as-needed basis

Hi there! We’re looking for a babysitter for our three children, aged infant, preschool, and elementary. The job starts on February 13th, but we can adjust the start date if needed. Your main tasks include watching the kids, preparing meals, and helping with homework. Playtime and activity planning... More

  • $18–23/hr
  • Bel Air, MD • 24 miles away

Looking for a regular sitter for 5 kids,...

  • 5+ children
  • Babysitting
  • M
  • T
  • W
  • T

Weekly

5:00am - 3:00pm

We are looking for a reliable babysitter for our five children, ages 3-14. This position is primarily caring for 3 year old while older kids are in school. Care is needed starting on March 2nd, Monday through Thursday. March-April hours will be 6 am to about 3 pm 2-3 days per week, after that hours... More

  • $22–26/hr
  • Middle River, MD • 18 miles away

Babysitter needed for 2 infant and toddler...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

Hi there! We need a reliable babysitter for our two children, an infant and a toddler. The job starts on February 6th. It’s important that you’re comfortable around our large dog, a cane corso, who does not require care. You should have a car to help with any needed activities. You’ll engage with... More

  • $22–28/hr
  • Annapolis, MD • 25 miles away

Sitter needed to transport 2nd grader from...

  • 1 child
  • Babysitting
  • M
  • T

Weekly

2:30pm - 3:30pm

Hello! We’re looking for a sitter to help with our child in elementary school. This position involves picking her up from school at 2:30 PM on Mondays and Thursdays, transporting her to an after school program which is only 10 mins from the school. Everything is located in Annapolis. Only pick up... More

  • $10–19/hr
  • Glen Burnie, MD • 24 miles away

Seeking babysitter with a car for 2 young...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

We want a babysitter for two children, ages preschool and toddler Quinlynn 3 and Chosen 1. The job starts on March 7th. You need experience with multiple children and your own car for transportation and emergency . You'll plan fun activities, prepare meals, and help with basic routines. Keeping the... More

  • $10–15/hr
  • Baltimore, MD • 23 miles away

Weekday School Transportation Needed...

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

Weekly

7:30am - 8:30am (flexible)

I am seeking a dependable, punctual person to transport my two children to and from school each weekday.

Mornings: Arrive at my home at 7:30 AM and drop the children at their designated schools.
Afternoons: Pick up the children by 5:15 PM (earlier if needed for traffic) and return them home.

Each... More

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