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Find a Babysitting Job in Chestertown, MD

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14 Babysitting Jobs Found

  • $24–26/hr
  • Annapolis, MD • 25 miles away

Seeking a babysitter starting January 26th...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hi! We're looking for a babysitter for our preschool child. The sitter needs to speak Spanish to help with communication and learning.

The job starts on January 26th and will include daily activities like playing games, reading stories, and preparing simple meals. You’ll also help with light... More

  • $14–25/hr
  • Severna Park, MD • 25 miles away

Seeking Dependable Babysitter for Two...

  • 2 children
  • Babysitting
  • S

One-time

Start date: 01/24

12:00am - 9:00am (flexible)

We need a reliable babysitter for two children, an elementary age child and a toddler. The job starts on January 24, 2026, at 7:30 AM. The start time is flexible, but the shift ends by 4:30 PM. You must have your own car and be comfortable with pets. Your responsibilities include supervising play,... More

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

Need a Reliable Babysitter with a Car for...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hello, we are looking for a babysitter to help with our toddler starting on January 17, 2026. Your main tasks will include playing, feeding, and keeping our child safe. You should have a car to help with outings and activities. We want someone who can engage with our child, follow their routine, and... More

  • $21–25/hr
  • Annapolis, MD • 21 miles away

Engaging Babysitter Needed for Active...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hello sitters! We are looking for a reliable babysitter for our toddler. This role is flexible, with a start date around February 2, 2026.

You will engage our child in fun activities, keep them safe, and help with daily routines like meals and nap times. It's important to have experience with... More

  • $19–22/hr
  • Bel Air, MD • 24 miles away

Seeking Friendly Babysitter for Elementary...

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

Weekly

6:00am - 9:00am (flexible)

Hello sitters! We’re looking for a babysitter for one child in elementary school. This position requires special needs experience. The schedule starts on December 15, 2025, but we can adjust the start date. The hours are from 6:00 AM to 8:30 AM, Tuesday through Friday. You will help with morning... More

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

Reliable Babysitter Needed for Two...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

We’re looking for a reliable babysitter to watch our two elementary school-aged children beginning on January 5, 2026. This role includes picking them up from school, preparing meals, and helping with homework.

You need a car to transport them to extracurricular activities. We want someone who can... More

  • $13–25/hr
  • Severna Park, MD • 25 miles away

Seeking Reliable Babysitter for Three...

  • 3 children
  • Babysitting

Occasional

On an as-needed basis

We are looking for a responsible babysitter to care for our three children, including a pre-schooler, a toddler, and an infant, starting on January 9, 2026, at 4:00 PM. The schedule is flexible. The ideal candidate will ensure a safe and engaging environment, manage activities, prepare meals, and... More

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

Seeking Reliable Babysitter with Car for...

  • 1 child
  • Babysitting
  • F
  • S

Weekly

1:00pm - 8:00pm

Could you help us by watching our toddler? We need a babysitter to start on January 17, 2026, every Friday and Saturday, from 1:00 PM to 8:00 PM.

You'll engage our child in speech therapy, reading and to prepare snacks, and ensure their safety. We want someone who can create a playful and safe... More

  • $15–20/hr
  • Perry Hall, MD • 22 miles away

Looking for a fun babysitter for my...

  • 1 child
  • Babysitting
  • T
  • W
  • T

Weekly

10:00am - 1:00pm

Hello! We’re looking for a babysitter for our toddler. The job starts on January 5, 2026, and takes place every Tuesday, Wednesday, and Thursday from 10:00 AM to 1:00 PM. Your main tasks include supervising playtime, and engaging in activities that support development. We need someone attentive,... More

  • $10–23/hr
  • Baltimore, MD • 22 miles away

Seeking Caring Babysitter for Two...

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

Weekly

12:00am - 8:00am (flexible)

We need a reliable babysitter for two children aged toddler and elementary. The job starts on December 31, 2025, at 3:25 PM, with some flexibility on the start date. Regular hours include Fridays, Saturdays, Thursdays, and Sundays from 1:00 PM to 9:00 PM. Your tasks will include supervising play,... More

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

Babysitter Needed for Two Elementary...

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

Weekly

2:30pm - 6:30pm (flexible)

Hi! We are looking for a babysitter for our two elementary-aged children. The job runs from 2:30 PM to 6:00 PM, Monday through Friday. We need someone to get the boys from the bus stop. You will help with homework, take to some sports/ activities, and prepare snacks. Flexibility with the start date... More

  • $21–25/hr
  • Severna Park, MD • 25 miles away

Looking for an after school sitter for...

  • 3 children
  • Babysitting
  • W
  • T

Weekly

2:00pm - 6:00pm (flexible)

We are looking for a fun, reliable, energetic sitter for our three kids. The job would include getting our 6 year old twins off the bus and walking them home. Other duties include snack preparation and homework help. Our 13 year old gets home at 4:20 and mainly takes care of herself.

We also... More

  • $10–25/hr
  • Nottingham, MD • 23 miles away

Babysitter Needed for 1 Toddler, Flexible...

  • 1 child
  • Babysitting
  • M
  • T
  • W

Weekly

12:00am - 2:00am (flexible)

3 days per week
• 2 hours per day

We are looking for a reliable and caring nanny to help with picking up our child from a daycare located near our home. The role is part-time and suitable for someone who lives nearby and enjoys working with children.

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