
"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.
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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.
Hello! I’m looking for a family in need of occasional childcare this school year. A little bit about me: After high school, I initially pursued a degree in elementary education. For three years, I worked full-time as a nanny for a family in Newton. I later shifted my focus to animal studies and am now a veterinary technician, but I still have nearly ten years of experience caring for children, including over three years as a lifeguard. I also have reliable transportation and would be happy to provide references.
Hi My name is Melinda, What I like most about childcare is being able to make a positive impact on a child’s day. I enjoy seeing their personalities shine as they grow and learn. It’s rewarding to know I can provide comfort, encouragement, and structure while also creating fun, memorable moments.” I’m comfortable with pets and in my past nannying jobs I’ve done food prep, light household chores and picking up And dropping off children. On a few occasions I’ve stayed with the kids as well at there activities which o love doing. I miss the days of my daughter playing sports and dance sessions. Looking forward to creating new experiences.
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 Stephanie and I am a current Teacher in Boston. I graduated from UMB majoring in Early childhood Education and English as my bachelors and Elementary Education as my Masters. I’ve been babysitting since I was 14 with nieces, nephews, friends little siblings and even my coaches kids. I have experience ranging from infants all the way to 13 year olds. I can help with homework, cooking food and creating a positive environment for your kids. I’m also pet friendly and have taken care of pets in the past! Outside of urban sitter I’m a full time classroom teacher which has helped me be more concious of creating a safe space and helped me take pride in my work with Restorative Justice practices. I hope to hear from you soon!
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

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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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