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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.

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Kay $19 per hour for 1 child

Hi! My name is Kay, and I’m a student at Emmanuel College in the Fenway area, where I’m pursuing a degree in Elementary Education. I have about three years of hands-on experience working with children from kindergarten through 8th grade, and I currently work in both pre- and post-school day programs as well as summer camps. Additionally, I have experience babysitting younger children, ages 2–4. Working with kids is truly my passion. My goal is to provide a safe, positive, and caring environment where children feel supported and engaged. I take pride in being patient, attentive, and responsible, and I always strive to make each child’s time with me fun, meaningful, and secure. I also have over five years of experience pet sitting both large and small dogs, as well as cats. I’m more than happy to take on household pet responsibilities, including feeding, walking, and providing attentive care while you’re away.

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Aniyah $25 per hour for 1 child

Hi families! I'm Aniyah, and I'm currently looking for part-time babysitting position. I'm a certified babysitter with First Aid, CPR, and BLS Certifications, and I truly enjoy working with children - whether that's helping with homework, planning fun activities, or keeping routines smooth and stress-free for parents. I also handle Lighthouse cleanup and meal preparation. I'm responsible, patient, and big on safety and communication. My availability is Monday, Wednesday, and Thursday from 12-6, and I'm open to recurring or Occasional positions or speaking about different times. Please feel free to reach out if you're looking for a sitter and have any questions. Thank you 😊!

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Maliyah $20 per hour for 1 child

Hello, I am Maliyah. I am 20 years old. I just moved to massachusetts in early November of 2025. I am originally from new york. I worked as a teaching assistant back in New york. I also am the eldest siblings with the age gap being over 10 years. I’d say i have lots of experience with different ages between 2-15. I am excited to start working with you.

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Zaineb $25 per hour for 1 child

Hi there! By day, I work in tech, but I’ve never stopped missing spending time with kids. In college, I babysat, tutored, and coached a girls’ soccer team, and I also spent a summer as a camp counselor. I’m still in touch with some of those families today, which means so much to me. I love getting to know each kid’s personality, cheering them on, and being a good mentor — and a little bit of an older sister, too. I’m happy to help with homework, explore the city, do crafts, play games, or wind down with a calm bedtime routine. I’d love to get to know your family and hopefully become someone your kids look forward to spending time with!

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Tori $21 per hour for 1 child

I’ve worked as a pre-k teacher for the past 4 1/2 years, frequently babysit and used to have 2 nannying jobs. I’m pretty decent with special needs kids and have worked with them before. I have been CORI checked, have no criminal background and am CPR, First aid and teacher certified. I’m playful and creative with children and encourage learning, boundaries, playing pretend, creativeness, and just fun all around! I am experienced, ambitious, organized, a good listener, / great rule/boundary follower, and kind, respectful, accommodating, outgoing and energetic. I’ve mainly only watched children but have also watched pets before. I have no experience watching seniors but am willing to learn and do it. I’ve also never house-sat but am again, willing to and am very responsible and great at cleaning and taking care of things and keeping it in check. I have a background with psychology and social work from college so I’m very good at reading children’s heads and understanding their personalities. I am also very protective of them because of my schooling in social work so I know how to watch and take care of them. I am currently going to college for nursing and am doing multiple interviews for more teaching positions at other schools because I recently got laid off because there was too many staff members.

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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

photo of quoted parent Madeleine

"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

stock photo of a 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

photo of quoted parent Catherine

"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

Family with caregiver

Find a wedding babysitter in Winchester

Browse profiles and read parent reviews for free.

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.

Resources

Preparing for your first babysitter

Tips for handing off your children to a new sitter.

Top questions to ask a babysitter in an interview

The top questions to ask when choosing a sitter.

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