
"Recommendations from friends are a must when it comes to a sitter for my kids. UrbanSitter has expanded our network of babysitters, and it has given us peace of mind."
Matt K., dad of two

Browse background checked babysitters near you in Winchester. Compare local reviews, rates, and experience to find the right fit.
Looking for jobs? Apply here.
Families in Winchester use UrbanSitter for date nights, after school help, and last-minute babysitting.
All babysitters shown here are background checked every year. Learn more.
Hi families! I'm Aniyah, and I'm currently looking for part-time babysitting position. I'm a certified babysitter with First Aid, CPR, and BLS Certifications, and I truly enjoy working with children - whether that's helping with homework, planning fun activities, or keeping routines smooth and stress-free for parents. I also handle Lighthouse cleanup and meal preparation. I'm responsible, patient, and big on safety and communication. My availability is Monday, Wednesday, and Thursday from 12-6, and I'm open to recurring or Occasional positions or speaking about different times. Please feel free to reach out if you're looking for a sitter and have any questions. Thank you 😊!
Hello, I am Maliyah. I am 20 years old. I just moved to massachusetts in early November of 2025. I am originally from new york. I worked as a teaching assistant back in New york. I also am the eldest siblings with the age gap being over 10 years. I’d say i have lots of experience with different ages between 2-15. I am excited to start working with you.
I’ve worked as a pre-k teacher for the past 4 1/2 years, frequently babysit and used to have 2 nannying jobs. I’m pretty decent with special needs kids and have worked with them before. I have been CORI checked, have no criminal background and am CPR, First aid and teacher certified. I’m playful and creative with children and encourage learning, boundaries, playing pretend, creativeness, and just fun all around! I am experienced, ambitious, organized, a good listener, / great rule/boundary follower, and kind, respectful, accommodating, outgoing and energetic. I’ve mainly only watched children but have also watched pets before. I have no experience watching seniors but am willing to learn and do it. I’ve also never house-sat but am again, willing to and am very responsible and great at cleaning and taking care of things and keeping it in check. I have a background with psychology and social work from college so I’m very good at reading children’s heads and understanding their personalities. I am also very protective of them because of my schooling in social work so I know how to watch and take care of them. I am currently going to college for nursing and am doing multiple interviews for more teaching positions at other schools because I recently got laid off because there was too many staff members.
Hi! I’m Adelaide, a senior majoring in Biochemistry and Molecular Biology at Belmont University. Originally from Quincy, IL, I grew up as the oldest of four sisters, and caring for them has always been a big part of my life. Alongside babysitting for other families, I’ve developed a strong background in childcare and responsibility from a young age. In addition to my family experience, I worked as a caregiver for two years during my sophomore and junior years, gaining hands-on experience caring for individuals across a wide age range. This work has deepened my understanding and appreciation of compassionate, attentive care for people of all backgrounds and needs.
Hi! My name is Malika, I am a Biology student at Northeastern University. I have been babysitting and looking after pets since I was 15/16. I have been with twins, toddlers, several dogs and have loved spending time with them! I am very enthusiastic and am also up for running errands and keeping homes clean and tidy.
Every babysitter's profile is individually reviewed by UrbanSitter's Trust & Safety team after clearing an annual background check. Rely on reviews from local families to help you find your best fit.

"Recommendations from friends are a must when it comes to a sitter for my kids. UrbanSitter has expanded our network of babysitters, and it has given us peace of mind."
Matt K., dad of two

"UrbanSitter has supported my needs for reliable and joyful sitters. Whether it be for work, recreation or last-minute emergencies, we've made wonderful relationships with local sitters who have become a part of our family!"
Natalie O., mom of five

"UrbanSitter is my go-to for quality sitters! I can book weeks ahead of time or easily find a same-day sitter when in a bind. I even hired a part-time nanny during a daycare transition. Customer service is helpful and babysitters respond in a timely manner."
Laura F., mom of two

Create a free account to view full profiles and more.
To sign up with Facebook, we need permission to use your email address.
Sharing your friends list is optional, and allows us to connect you with sitters they book and recommend. Nothing will be shared or posted.

Create a free account to view full profiles and more.
To sign up with Facebook, we need permission to use your email address.
Sharing your friends list is optional, and allows us to connect you with sitters they book and recommend. Nothing will be shared or posted.
In addition to background checks, sitters are evaluated by real people to meet our gold standard for Trust & Safety.
Need a sitter today? Last-minute babysitter requests receive a response in under two minutes in most cities.
See babysitters recommended by local families, including parents in your school, neighborhood, and parent groups.
Compare reviews, response times, repeat families, and profile details so you can hire with confidence.