
"Savannah was very sweet playing with our infant. He was very happy taking a bottle from her, going on a walk, and reading a book."
Talia L., parent

Meet infant babysitters Winchester families trust, with parent reviews, background checks, and detailed profiles.
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Families in Winchester use UrbanSitter for date nights, newborn care, overnight babysitting, and last-minute infant sitters.
45 available today | Avg hourly rate: $24.68/hr
All babysitters shown here are background checked every year. Learn more.
Hi families! I’m a former au pair and professional nanny of 4 years. I have 900+ verified hours as a volunteer at a daycare in South Africa. I’m a quick learner and can easily adapt to new routines and responsibilities. I do have a valid driver’s license with driving experience in all weather conditions and different car types. I am comfortable around small dogs and friendly cats. I am comfortable with light house cleaning(light sweeping, dishes, light laundry, tidying up) and can assist with homework. I am a bit silly and fun but always within reason. If needed I can whip up quick meals too!
Hi! My name is Evie, and I’m a college student at Boston University majoring in Fine Arts. I have over 5 years of experience as a babysitter and pet sitter, I am certified in First Aid and CPR and strive to create a safe, engaging, and positive environment for every child I care for!
Hi! My name is Sam, and I have over 10 years of experience caring for children of all ages — from infants to pre-teens. I’m passionate about creating a fun, safe, and nurturing environment where kids can learn and grow. I’m dependable, patient, and love engaging kids through crafts, reading, and outdoor activities. My goal is always to make sure your children feel happy, supported, and secure while you’re away.
Hello! My name is Abby and Im a 2nd grade teacher! I currently live in Medford. I did a lot of sitting as a teen, especially when I was going into teaching. I worked at Lowell catholic elementary as a spanish and art teacher along with assisting with the extended day program. I also was a preschool summer school teacher preparing kids with "kindergarten readiness." | worked with a lot of age groups ranging from infant-12. I worked at lowell general as a pediatric/ mother infant patient care technician while I'm in nursing school. I have a lot of experience with kids and absolutely adore working with them and providing the care that they need! I am also CPR certified! I also have dogs at home and am very comfortable with pets! I am also fully covid vaccinated.
Hey Parents! My name is Melissa, I am 31 years old, have about 5 years experience nannying. Ages 6months - 14 years and I am currently looking for full-time jobs. I have worked in the past with different families from one-time jobs to recurring positions. I am available Monday - Friday and occasionally on weekends. I also have my own vehicle for transportation. If you have any questions feel free to ask! Thanks!

As of November 2026
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team. See reviews from Winchester parents before you book.
262 sitters background checked in Winchester, MA
4.9 average star rating from 633 parent reviews in Winchester

"Savannah was very sweet playing with our infant. He was very happy taking a bottle from her, going on a walk, and reading a book."
Talia L., parent

"Leanna was very sweet and good with our daughter. She played with her, changed her diaper, fed her and all the good things that a newborn needs."
Rachel M., parent

"Was our first time leaving our newborn with a sitter. Emily's calm demeanor put us at ease when we left, and she was great about sending us updates."
Andrea Z., parent

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Browse profiles and read parent reviews for free.
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.
See infant babysitters connected to families in your Winchester neighborhood. Know who nearby parents rely on for infant care.
Detailed profiles show each babysitter's infant experience, listed skills, certifications, and qualifications.
Read reviews from local families who have trusted their infant with a sitter. See which babysitters are repeat favorites.
Every babysitter completes an annual background check, and every profile is reviewed by our Trust and Safety team.
Tips for easing your baby into care with a new nanny or sitter.
Average babysitting rates in Winchester and across the country.