"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
Find a wedding babysitter in Winchester, MA
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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58 experienced babysitters in Winchester, MA
Families in Winchester turn to UrbanSitter for wedding and special event babysitting.
46 available tonight | Avg hourly rate: $24.63/hr
All babysitters shown here are background checked every year. Learn more.
Sophie
$25 per hour for 1 child
Booked by 3 repeat families
3 reviews$25 per hour for 1 child
Booked by 6 families in Winchester, MA
As a compassionate caregiver, I provide nurturing support and companionship to both children and seniors. With a genuine dedication to enhancing their well-being, I offer attentive care, fostering a safe and enriching environment tailored to their unique needs. From facilitating activities that promote growth and development to offering assistance with daily tasks, I prioritise comfort happiness and dignity of those under my care. I am a former Au Pair with lots of child care experience who also majored in Early childhood Development.
“Sophie was lovely and she also cleaned our kitchen while kids slept which was so amazing to come home to!”
Teagan 1 review
$15 per hour for 1 child
$15 per hour for 1 child
Booked by 1 family in Winchester, MA
Hello! My name is Teagan and I have been working with kids of all ages for about 11 years. I have experience working with children from ages 0-16. Please reach out if you have any questions! Thanks!
“Teagan looked after my son (four and a half months old) during the day while I ran some errands. She was energetic when she walked in and it was clear she knew a baby of his ages rhythm. Luca didn’t take a long nap like he typically does by Teagan was able to calm him down and do some more chilled playtime. She was also communicative throughout the day.”
Andrea 1 review
$28 per hour for 1 child
$28 per hour for 1 child
Hi! I am an experienced, multilingual and licensed educator, with over 20 years of experience. I offer childcare, tutoring, pet and elderly care. I excel at working with neurodiverse individuals, children and teens.
“Andrea has always been wonderful with my girls (ages 3 and 5). She brings the very best of herself, as both a mom and an educator, to the time she spends with them, always doing arts and crafts, science experiments, and reading books. She is warm, loving, and also able to navigate their nonsense with firm kindness. Ever since my youngest daughter was tiny, there were times when Andrea was the only person I could trust to calm her when she was experiencing separation anxiety and inconsolable. Andrea is a gem!”
Anna
$25 per hour for 1 child
Booked by 2 repeat families
4 reviews$25 per hour for 1 child
Booked by 6 families in Winchester, MA
I am starting grad school in the fall and looking for part time babysitting jobs. I have experience babysitting babies, toddlers, and kids from ages 3-10. I enjoy art, hiking, reading, and playing piano.
Deborah $25 per hour for 1 child
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.
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How much does a wedding babysitter cost in Winchester, MA?
- Average hourly rate for 1 child: $24.63
- Average hourly rate for 2 children: $29.83
- Typical job length: 4.3 hours
- Most requested times: Afternoon
As of November 2026
Recent babysitter activity in Winchester, MA
Hiring a wedding babysitter starts with trust
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team.
264 sitters background checked in Winchester, MA
4.9 average star rating from 633 reviews in Winchester, MA
"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
Find a wedding babysitter in Winchester
Browse profiles and read parent reviews for free.
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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.
Find a wedding babysitter in Winchester
Browse profiles and read parent reviews for free.
We use email to send essential communication regarding your account.
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.
Why Winchester families use UrbanSitter for wedding child care
Easy to start, no pressure to hire
Share the wedding date and babysitting details, then hear from available sitters. Review your options and hire only if you find the right fit.
Your choice of sitter
Browse profiles, read reviews from other parents, and pick the babysitter you feel best about. No agency assignments.
Background checked, every year
Every babysitter completes an annual background check. See bookings, repeat families, and reviews from local parents.
Hotel, venue, or overnight
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.
Frequently asked questions about wedding babysitters in Winchester
How do I find a wedding babysitter in Winchester?
Share the wedding date, location, times, and number of children you need care for on UrbanSitter. Available babysitters in Winchester can respond, and you can browse profiles and set up a phone interview before booking. There is no obligation to hire unless you find a fit.
How much does a wedding babysitter cost in Winchester?
As of November 2026, babysitting rates in Winchester average $24.63 per hour for one child. Rates vary by experience, number of children, and job length. For special occasions or longer bookings, some families offer a higher rate. See average babysitting rates in your area.
Are babysitters in Winchester on UrbanSitter background checked?
Yes. Every babysitter on UrbanSitter completes an annual background check, including those in Winchester. Each profile is individually reviewed by our Trust and Safety team. See what's included in the background check.
Can a babysitter watch kids at the hotel or wedding venue?
Yes. When you share your care needs, include the care location, whether that is a hotel room, a kids' room at the venue, or somewhere nearby. Many babysitters in Winchester are comfortable with both on-site and off-site care. Let the sitter know about any planned activities so the kids stay entertained while you enjoy the celebration.
How far in advance should I book a wedding babysitter in Winchester?
Two months out is a good starting point to look for a wedding babysitter. That gives you time to browse candidates, read reviews, and schedule an interview if you would like to connect before the event. UrbanSitter also works well on shorter timelines.
What if I am not from Winchester and need a wedding babysitter?
Whether you are attending a destination wedding or visiting Winchester for the celebration, you can use UrbanSitter to find a wedding babysitter. Start by submitting your request, and available babysitters in Winchester can respond. Next, browse profiles and read reviews from local families to find a fit. You can also schedule a phone or video interview before your trip for added peace of mind.
