
"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.
Looking for jobs? Apply here.
Browse background checked babysitters near you in Winchester. Compare local reviews, rates, and experience to find the right fit.
Looking for jobs? Apply here.
Families in Winchester use UrbanSitter for date nights, after school help, and last-minute babysitting.
All babysitters shown here are background checked every year. Learn more.
Hello! My name is Helen, and I am an experienced babysitter, tutor, and teacher. I recently passed the bar exam and am looking to pick up some occasional work during my full-time job search. I love the outdoors and engaging children in imaginative play and prefer to minimize screen time when possible. I like helping kids create, learn, and have fun in ways that build their independence and self-esteem, while maintaining a safe and supportive environment. I look forward to working with you and your child(ren)!
“Helen was professional and communicated well, on time, and the kids loved her.”
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.
Bilingual (English–Spanish) caregiver with over 8 years of experience nurturing and educating children from infancy through school age. I bring 3–5 years of hands-on care for infants and 5–10 years supporting toddlers and school-aged children in their daily routines, development, and learning. Former Au Pair with a Bachelor’s degree in Business Management and CPR certification for children, I am known for creating safe, structured, and engaging environments where children can thrive. My approach blends respect, discipline, and positive behavior reinforcement, helping children build confidence and independence while learning through play, creativity, and exploration. Gifted in dancing, painting, and acting, I integrate art and movement into daily activities to encourage imagination, coordination, and emotional expression. Families appreciate my warm, responsible nature and my ability to form strong, trusting relationships based on open communication and care.
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.

"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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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.
In addition to background checks, sitters are evaluated by real people to meet our gold standard for Trust & Safety.
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