
"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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Hello, my name is Deborah and I am a recent graduate of the University of Michigan, where I obtained my degree in Biomedical Engineering. I currently work as a Biotech Engineer, and will begin my Master's degree in Fall 2026. I have received my Basic First Aid Training and completed the Red Cross CPR certification course. I love showing my love to others through cooking meals and love to read in my free time. In caring for your child, I love to engage them through reading, educational games, puzzles and a lot of time outside. In past roles I've been responsible for meal prep, light housekeeping, school pickup/drop off and overnight care.
Nannied for a family of 4 (full-time) for 15 years. Overnight, Vacations and Daily care. I use a variety of different child-care philosophies (e.g. RIE, attachement, gentle care giving) I would say I am most aligned with “holistic” care-giving. Dependent of what each persons specific needs are. Meeting peoples emotional needs and watching them thrive is a great joy of mine. Full spectrum doula. Newborn and Night Nanny. Confident in gentle sleep training. (not crying it out) I’ve been involved in the homeschool/unschooling community for 15+ years. I have a degree in psychology, specifically behavior modification, and feel confident giving care to anyone with low-moderate needs. I am also a certified yoga teacher and was a lifeguard for many years. I am experienced in light household chores as well as having deep roots in nutrition, specifically anti-inflammatory diets. My personality is generally relaxed but I am fiercely loyal to the children in my care, meaning I need to work with a family that also views their child/children as complete people and treats them with respect. :) Also I appreciate adults who can be forward and up front about their boundaries and what they want from a caregiver.
Hi my name is Cristina, I have a lot of personal experience with taking care of people such as my grandmother and my nieces, I also was a camp counselor for DARTS a camp run by the Boston symphony orchestra where I shared my passion for the performing arts and helped the campers use their creativity to put on plays, create dance choreographies and so much more, when it’s not cold or rainy outside I also like to go on fun adventures to new exciting places around Boston :)
With over ten years of experience in child caregiving, I have developed a deep passion for supporting and nurturing children. Starting as a babysitter at the age of 12, I have worked with kids ranging from 9 months to 17 years old. My experience includes tutoring dyslexic students, working at a summer camp, and providing care for children with special needs. Currently, I serve as a behavioral therapist for autistic children, where I apply tailored strategies to support their growth and development. I am dedicated to creating positive, enriching experiences for every child I work with.
My name is Meryem. I am a doctoral student and professional babysitter with several years of experience caring for children of all ages. I am passionate about early childhood education and love creating a safe, engaging, and fun environment for children to learn and grow. I am CPR/ First Aid certified.
“She is very good ”

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.
273 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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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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