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Find a Babysitting Job in Chestertown, MD

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25 Babysitting Jobs Found

  • $22–26/hr
  • Pasadena, MD • 21 miles away

Babysitter needed for four children, ages...

  • 4 children
  • Babysitting

Occasional

On an as-needed basis

Hi, we are looking for a babysitter for our four children, who are in elementary and middle school. The start date for this position is April 10th. The ideal candidate has a car and can safely transport the kids to activities or appointments. Responsibilities include overseeing homework, preparing... More

  • $16–22/hr
  • Rosedale, MD • 22 miles away

a Morning Sitter Needed (5:30–7:30 AM)...

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

Weekly

5:30am - 7:30am

Seeking a reliable morning sitter for my preschool-aged son on a biweekly schedule: Week A (Mon–Wed) and Week B (Friday only), 5:30–7:30 AM. Duties include supervising his morning routine and safely dropping him off at preschool by 7:30 AM. Must have a valid driver’s license, reliable... More

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

Seeking a babysitter for two toddlers...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

We're looking for a babysitter to help with two children, ages toddler and middle school. The role requires someone with experience in managing multiple kids at once. A driver’s license and personal vehicle are essential for local outings and activities. The job is flexible, starting around February... More

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

Babysitter needed for toddler, flexible...

  • 1 child
  • Babysitting
  • T

One-time

Start date: 03/19

8:00am - 5:00pm (flexible)

Hello sitters! We need a babysitter for our toddler starting on March 19th. The work hours are flexible, but will be from 8:00 AM to 5:00 PM. You will look after one child and ensure they have a safe and fun environment. Creatively engaging in play and activities is important. We have a large... More

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

Seeking a babysitter with a car for three...

  • 3 children
  • Babysitting
  • M
  • T
  • W
  • T
  • F

Weekly

5:30am - 3:30pm

We want a babysitter for three children aged toddler, preschool, and elementary. The job starts on February 16th and runs Monday to Friday from 5:30 AM to 3:00 PM. You will prepare meals, help with playtime activities, and assist with homework. The ideal candidate has experience with multiples and... More

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

Babysitter needed for two children, Sunday...

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

Weekly

5:30pm - 9:30pm (flexible)

Hello sitters! We want a dedicated individual to look after our two children, ages toddler and pre-school. The job starts on February 18th, with a flexible start date. You will work daily from 5:30 PM to 9:00 PM. Responsibilities include preparing meals, playing games, and assisting with bedtime... More

  • $18–25/hr
  • Pasadena, MD • 21 miles away

Babysitter needed for 1 preschool child;...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hi there! We’re looking for a babysitter for our preschool child. The start date is March 26th, but we're flexible. The job involves engaging our child in fun activities, preparing simple meals, and ensuring their safety and well-being. You should be comfortable around our large dog, a labrador... 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

  • $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

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