
"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.
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Families in Winchester use UrbanSitter for date nights, after school help, and last-minute babysitting.
42 available tonight | Avg hourly rate: $24.47/hr
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Hi! My name is Yvonne, and I am a responsible, caring, and trustworthy nanny with hands-on experience caring for children of different ages. I currently work as a nanny and I’m looking to fill in extra days when I’m available. I am a mom of two children, which has given me a deep understanding of children’s needs, routines, and emotional care. I truly enjoy creating a safe, loving, and structured environment where kids feel comfortable and happy. I am flexible and always respectful of parents’ preferences and routines. I have my own car and reliable transportation. I’m also comfortable caring for pets, as I have a dog myself and love animals. My primary language is Spanish, and I have an intermediate level of English. I am always open to learning and improving my language skills. I take my work seriously and treat every family and child with care, patience, and respect. I would love the opportunity to support your family!
Hi! My name is Olivia and I'm currently a graduate student at Simmons University. I am offering child care and household services. I've worked as a teaching assistant in several elementary schools and have worked specifically with children with special needs. I worked as an assistant teacher in Howell NJ with children preschool-kindergarten and 1st-2nd grade for three summers. I also worked most recently as a teacher's assistant in Easton PA for 2nd grade students, tutoring in reading and math. I worked as a teacher in my local church's Sunday school for four years, working with kids between 3rd-5th grade. I love working with kids of all ages and engaging with them in whatever their interests may be! I can offer tutoring in math, history, reading/writing, art lessons, as well as beginner lessons in Latin and Russian. I love arts and crafts, playing sports (especially tennis and dance), and reading. I'm available for household services such as cleaning, running errands, and laundry.
I am in New York City for the summer in the middle of my MSW program at Simmons University. I have extensive experience working with children in a variety of capacities (school counselor, teacher assistant, afterschool assistant, ABA assistant therapist, school social work intern, babysitter) I am a somewhat recent graduate from Boston College with an Applied Psychology and Human Development B.A. I am currently pursuing my MSW at Simmons University and am looking to help families with occasional or part-time babysitting, pet sitting, or other services. If you would like to discuss more, I can forward my resume and/or references. I would love to hear from you :)
Hello! My name is Kathleen, I am a college student here in Boston offering childcare, household, and pet care services. I have a surplus of childcare experience between assistant teaching Dance classes since 2019, head coaching gymnastics for 3 years, and the past three summers I have been an overnight camp counselor. I have worked with kids from ages 4-15 between all three positions. I have a sufficient experience with house and pet sitting. Please feel free to reach out with any questions!
I am college student here at Fisher College looking to help out on my free time. I was a preschool teacher for 1-3 year olds during the summer and I loved working and teaching them. I also have a passion for animals and my whole life I have lived and grown up with dogs and cats. I have a dog named Maia and a cat named Beatrice so any help needed with pets are my expertise. I am very passionate about what I do and want to always provide the best support and help for any client or parents (pet parents too!).

As of October 2026
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.
272 sitters background checked in Winchester, MA
4.9 average star rating from total of 584 reviews in Winchester, MA

"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

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Sharing your friends list is optional, and allows us to connect you with sitters they book and recommend. Nothing will be shared or posted.
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