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Find a Babysitting Job in Chestertown, MD

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20 Babysitting Jobs Found

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

Babysitter needed for one preschool child...

  • 1 child
  • Babysitting
  • S

One-time

Start date: 02/14

6:30pm - 11:30pm

We want a reliable babysitter for our preschool child. This role includes supervising playtime, preparing snacks, and engaging in educational activities. The job starts on February 14th, with a schedule from 6:30 PM to 12:00 AM.

You will ensure safety and comfort, handle bedtime routines, and... More

  • $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

  • $14–16/hr
  • Middle River, MD • 18 miles away

Looking for a reliable babysitter for a...

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

Weekly

9:00am - 5:00pm (flexible)

Looking for a caring babysitter for one toddler, starting February 1, 2026, with flexible start date. Schedule includes Monday through Friday from 9:00 AM to 5:00 PM. Responsibilities include supervising play, preparing snacks, and engaging in age-appropriate activities. Must have prior experience... More

  • $15–24/hr
  • Annapolis, MD • 25 miles away

Babysitter needed for toddle comfortable...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We're looking for a reliable babysitter to help us with our toddler. The start date is February 6th, but we can be flexible. The sitter ideally speaks Spanish and be comfortable around our large dogs, who don;t need any care. Your main tasks include supervising playtime, preparing simple meals, and... More

  • $20–26/hr
  • Middle River, MD • 18 miles away

Needed: Babysitter for 2 Kids, Starts...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

Hi! We’re looking for a babysitter for our two children, ages toddler and elementary. The start date is February 4th.

The ideal person has experience with multiple children and a car for transportation needs. Responsibilities include supervising playtime, preparing snacks, and helping with... More

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

Occasional Babysitter needed for one three...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hello sitters! We're looking for someone to occasionally babysit our three year old daughter The role involves engaging our child in fun activities, ensuring their safety, and maintaining a positive atmosphere at home. You'll be comfortable around our pets, which include a large cockapoo and a cat.... More

  • $19–23/hr
  • Kenton, DE • 25 miles away

Seeking reliable sitter with a car for two...

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

Weekly

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

We're looking for a reliable babysitter for our two children, ages infant and toddler. The schedule starts on February 10th and is flexible, with hours from 8:00 AM to 4:30 PM, Monday through Friday. Your responsibilities include supervising playtime, preparing snacks and meals, and helping with nap... More

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