
"Katrina watched our son while we were in town for a wedding. She was timely, so nice and sent great pictures throughout the evening. He looked like he was having more fun than we were!"
Madeleine B., parent

Planning a wedding or attending one in Winchester? Hire babysitters loved by local families. Browse profiles and see who's available for free.
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Families in Winchester turn to UrbanSitter for wedding and special event babysitting.
42 available tonight | Avg hourly rate: $24.66/hr
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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.
262 sitters background checked in Winchester, MA
4.9 average star rating from 633 reviews in Winchester, MA

"Katrina watched our son while we were in town for a wedding. She was timely, so nice and sent great pictures throughout the evening. He looked like he was having more fun than we were!"
Madeleine B., parent

"Caitlin was awesome and jumped right in to chaperone four girls (10, 9, 8 and 6) at a family wedding (they were bridesmaids) and she was very helpful with the event as well as taking them home and putting them to bed."
Lila P., parent

"McKenna was great with our 3 year old son! She came prepared with a box of fun activities and handled playing, dinner, and bedtime seamlessly... and it was all at our hotel while we were in town for a wedding. Thank you McKenna!"
Catherine B., 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.
Share the wedding date and babysitting details, then hear from available sitters. Review your options and hire only if you find the right fit.
Browse profiles, read reviews from other parents, and pick the babysitter you feel best about. No agency assignments.
Every babysitter completes an annual background check. See bookings, repeat families, and reviews from local parents.
Whether it is a hotel room, a kids' room at the venue, or late-night care, book one sitter or several to fit the plan.