Sittercity home

Find a Babysitting Job in Winchester, MA

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

143 Babysitting Jobs Found

  • $20–25/hr
  • Somerville, MA • 4 miles away

Babysitter Needed for Elementary Child...

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

Weekly

2:30pm - 6:30pm

We're looking for a reliable babysitter to start on January 13, 2026.
The schedule is:
Tuesday: 2:30–6PM
Wednesday: 1–6PM
Thursday & Friday: 2:30–6PM
(Total: 16.5 hours per week)

Your responsibilities will include school pickup, engaging in playtime, helping with homework, and preparing meals.... More

  • $28–32/hr
  • North Weymouth, MA • 18 miles away

Occasional babysitter needed for infant

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We are looking for a responsible babysitter to care for our infant on January 3rd, 5-11pm. We would like you to come regularly beforehand to get to know our daughter and will likely need occasional help after January 3rd. You will be responsible for feeding, changing, and playing with our daughter.... More

  • $25–29/hr
  • Marblehead, MA • 15 miles away

Seeking Babysitter with a Car for Middle...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We want a reliable babysitter for our high school freshman This role starts on December 13, 2025, but the start date is flexible. You'll need to have a car to help with transportation as needed. Your main tasks include supervising, assisting with homework, and just being around to make sure he is... More

  • $15/hr
  • Dorchester Center, MA • 12 miles away

“Babysitter needed for one infant on the...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We’re looking for a babysitter for our infant. You will engage with our little one through playtime, feeding, and changing diapers. It's important to create a safe and nurturing environment. We need someone who can follow our established routines and keep our child entertained. Light housekeeping... More

  • $25–31/hr
  • West Roxbury, MA • 12 miles away

One-day care for a Toddler (18mo girl)

  • 1 child
  • Babysitting
  • W

One-time

Start date: 11/26

12:00am - 4:00am (flexible)

I am looking for help with our toddler, Irene, for daycare for a day on 11.26 half day because our regular daycare is going to be closed. We are flexible on start/end time but approximately: 8:30 AM-4:30 PM. You'll be engaging her with activities: drawing, reading books, playing (e.g. with blocks... More

  • $17–28/hr
  • Methuen, MA • 19 miles away

Seeking a Reliable Babysitter with a Car...

  • 2 children
  • Babysitting

Occasional

On an as-needed basis

Hi there! We need a reliable babysitter for our two children, ages elementary and middle school… Please email me so we can set up a time to chat and meet! There is no true start date, it we do want to have a babysitter lined up as we go out on occasion… thank you!

  • $16–24/hr
  • Haverhill, MA • 21 miles away

Need Babysitter for Toddler, Flexible...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

We’re looking for a reliable babysitter for our toddler. The job starts on December 11, 2025, but we can adjust the start date if needed. You must have a car to take our child to activities or the park. You will prepare simple meals, play fun games, and help with daily routines like naptime. The... More

  • $25–31/hr
  • West Roxbury, MA • 12 miles away

One-day care for a Toddler (18mo girl)

  • 1 child
  • Babysitting
  • W

One-time

Start date: 11/26

12:00am - 4:00am (flexible)

I am looking for help with our toddler, Irene, for daycare for a day on 11.26 (half day) because our regular daycare is going to be closed. We are flexible on start/end time but approximately: 8:30 AM-4:30 PM. You'll be engaging her with activities: drawing, reading books, playing (e.g. with blocks... More

  • $25–30/hr
  • West Roxbury, MA • 12 miles away

Babysitter for a day - 18mo old girl

  • 1 child
  • Babysitting
  • T

One-time

Start date: 11/25

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

Hello!

I am looking for help with our toddler, Irene, for daycare for a day on 11.25 and morning of 11.26 (edited/updated) because our regular daycare is going to be closed. We are flexible on start/end time but approximately: 8:30 AM-4:30 PM. You'll be engaging her with activities: drawing,... More

  • $25–29/hr
  • Boston, MA • 10 miles away

Seeking Spanish-Speaking Sitter for Infant...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hello sitters! I am looking for a reliable babysitter for my infant starting on January 12, 2026, with some flexibility on the start date.

You will spend time with my little one, ensuring their safety and happiness. You’ll handle feeding, changing diapers, and engaging them in safe activities.... More

  • $20–24/hr
  • Quincy, MA • 16 miles away

Looking for a babysitter for 10 year old...

  • 1 child
  • Babysitting
  • W

One-time

Start date: 12/03

4:30pm - 11:30pm (flexible)

Looking for a caring babysitter for my 10 year old daughter. She very sweet and inquisitive. Im looking for a sitter for Dec 3, 2025 at 4:30pm, with a flexible starting time and ends at 11:30 PM on the same day. You should be comfortable with having a cat around and able to create a safe, fun... More

  • $25–32/hr
  • Hingham, MA • 20 miles away

Nanny needed for 2.5yr old boy in South...

  • 1 child
  • Babysitting
  • M
  • W

Weekly

8:30am - 5:30pm (flexible)

Hello sitters! We are seeking a fun, loving and responsible nanny for our 2.5 year old son on Mondays and Wednesdays, starting likely around mid December 2025. The hours are from 8:30 AM to 5:30 PM. Would love if you were bilingual and spoke Portuguese or Spanish (English too). Nanny should have... More

  • $25–32/hr
  • Hingham, MA • 20 miles away

Seeking Babysitter for Preschool Child on...

  • 1 child
  • Babysitting
  • M
  • W

Weekly

8:30am - 5:30pm (flexible)

Hello sitters! We need help with one preschool child on Mondays and Wednesdays. The starting date is flexible, but we’d like to begin around December 8, 2025. You’ll arrive at 8:30 AM and leave by 5:30 PM. It’s important that you have a car for activities and outings. Your main tasks include making... More

  • $25–29/hr
  • Roxbury, MA • 12 miles away

Babysitter/school pick needed 2 Wednesdays...

  • 1 child
  • Babysitting

Occasional

On an as-needed basis

Hi, I'm looking for a babysitter for my four-year-old starting on December 3, 2025. You will need to pick him up from preschool, either by car, using the MBTA, or on foot, at 4:50 pm in Jamaica Plain, and bring him home, approximately 1.1 miles away/1 MBTA stop away in Roxbury. You will need to keep... More

  • $25–29/hr
  • Arlington, MA • 2 miles away

Support Three Children Ages Pre-School and...

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

Weekly

7:00am - 10:00am

Hi there! We’re looking for a reliable babysitter for three children aged preschool and elementary. The job starts on January fifth, 2026, and runs from 7:00 AM to 10:00 AM, Monday through Friday.

You need to have a car and previous experience with multiple children. Your duties include, dress the... More

Babysitting FAQ

Jump to Top

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

Register now