
"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: $24.51/hr
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Hi my name is Ashley, I am a 1st Dental Student living in Boston. I am offering childcare and pet sitting services. I have been CPR certified for over 5 years. I love babysitting! I have been caring for children since I was 8 years old. I enjoy playing games, tutoring and keeping kids busy. I am open to pet sitting small - medium sized dogs as I have been a dog mom for the past 10+ years.
I am a tutor who thrives on helping k-8 students work more successfully in reading and writing. Special Education and literacy are my background with a solid foundation in The Science of Reading and Guided Reading, remedial reading and writing. I have 20 years of experience and a very nurturing manner. I prepare 3/4 year old with readiness skills for school also. I have several parent and teacher references. My skills include working with beginning, intermediate and advanced learners, mostly special needs learners, mild to moderate and English language learners in reading and writing. I also do childcare with ages three to ten. We work on creative play, storytelling, books, language, behaviors, sports, exercise and more, whatever your child's interests are is okay with me. My fees range according to service providing and number of students/children. I work mostly afternoons and evenings for the school year according to my primary position. I like to work all summer days too. I like to be flexible for you.
Hi there! I'm Allie, and I'm a Boston-based college professor and professional actor. I’m currently on summer break and available for short-term childcare opportunities! A bit about me—I moved to Boston to pursue my MFA in Theatre Education at Emerson College, but before that I lived in New York City, where I worked as a full-time nanny (and professional actor!). I have over ten years of childcare and children's education experience, and I'd love to meet you and your family. As a babysitter, I understand that every child and family is unique. I specialize in working with school-age children, children with severe allergies, children of LGBTQ+ families, high net worth families, and children with extra support needs (Prader-Willi syndrome, autism, ADHD, dyslexia, anxiety disorder, mood regulation disorder). I work carefully with parents to create a customized care plan to help their children thrive socially, emotionally, and academically. And as a professional actor, I also love to have fun and encourage imaginative play! My full resume and references are available upon request. I look forward to connecting with you soon!
“Ali is great and so creative — our girls had the best time. ”
Hello! My name is Joanna. I am originally from Cape Cod and am currently live in the Boston. I hold a Master’s degree in Community Development and Planning (specializing in Youth Development) from Clark University. While I currently work in clean energy, I have over a decade of hands-on experience in education and childcare. Throughout my career, I’ve cared for children of all ages, from newborns to teenagers. My background includes serving as a Youth Counselor at the Worcester Boys & Girls Club, tutoring for a college success program, and providing long-term babysitting and nanny-share support for families across Boston and Worcester. Previously, I served as a mother’s helper for a family with a 1-year-old and a 4-year-old. In that role, I managed morning routines, school drop-offs, tidying, outings to local parks, and occasional date-night care. Coming from a large family with many nieces and nephews, childcare has always been a natural part of my life. I love creating engaging, creative environments where children can explore, learn, and grow. I view caregiving as a mutual exchange where kids learn from me, and I learn just as much from them!
“Joanna is the most caring, calm, wonderful person. Our children love her (and so do we), and run to her each time she arrives because she is such a joy. She's reliable, punctual, responsible, and has a wonderful way with children. I cannot recommend her highly enough!”
Hello! My name is Star and I have been described as a positive, patient, and attentive caregiver. I am a recent graduate of the University of Massachusetts Amherst with my bachelors degree in horticultural science with a business focus. I have worked with Children in many summer camp settings, including two summers at Amherst recreation as a lead counselor. I have also spent much of my young adult adulthood babysitting, taking care of children from ages 2 to 14. I am currently a afterschool teacher at Baker elementary school working with kids from grades one to six. I am reliable and can do household tasks like laundry, cooking, and basic cleaning.

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.
271 sitters background checked in Winchester, MA
4.9 average star rating from total of 586 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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