
"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 Ashland? Hire babysitters loved by local families. Browse profiles and see who's available for free.
Looking for jobs? Apply here.
Families in Ashland turn to UrbanSitter for wedding and special event babysitting.
All babysitters shown here are background checked every year. Learn more.
Hi! I’m Amelia, I am currently a college student studying psychology and an associate teacher in an early childhood care center. I’ve spent years working with children of all ages; infants, toddlers, preschoolers, and school‑age kids, through babysitting, teaching, youth leadership, and community programs. I love getting to know each child’s personality and creating an environment where they feel comfortable, supported, and excited to be themselves. With infants and toddlers, I’m confident with feeding, diapering, soothing, nap routines, sensory play, and early developmental milestones. I’m calm, patient, and very comfortable reading cues and creating a predictable, nurturing space. With older kids, I enjoy homework help, creative projects, outdoor time, structured activities, and supporting emotional regulation and independence. I adapt easily to shy, energetic, sensitive, or spirited kids and meet them exactly where they are. I’m passionate about helping children explore the world around them. Whether that’s going outside, doing hands‑on activities, or finding small everyday moments that spark curiosity and joy. Families describe me as warm, reliable, organized, and easy to communicate with. I value building strong relationships with parents and keeping communication clear and consistent. I’m CPR and First Aid certified, comfortable with pets, don’t smoke, and happy to help with light housekeeping, meal prep, and maintaining routines. My goal is always to create a safe, nurturing environment where children can learn, play, and grow confidently. Please be sure of your hours before booking. You are responsible for the full hours listed, even if you arrive home early. I’m more than happy to extend hours as long as there is clear communication ahead of time. This helps me plan my schedule and ensures I can give your family the best care possible.
Hi! My name is Kaillyn, I’m 19 and a responsible, calm, and reliable caregiver with experience working with children and babysitting my younger cousins. I’m CPR & First Aid certified (renewing April) and very safety-focused. I’m comfortable with routines, meals, homework help, and bedtime, and I always aim to create a fun, safe, and supportive environment for kids. I’m happy to do a call beforehand and look forward to helping your family!
Hi! My name is Hilary, and I’m a nursing student at Simmons University. I’m genuinely passionate about well-being, caregiving, and helping families feel supported. I’m also interested in pediatrics long-term, so working with kids is something I take seriously and truly enjoy. I have been a care taker for more than 5 years. I’m offering care for children ages 2–10 and also senior care,companionship. I have experience working in assisted living, so I’m comfortable supporting older adults with patience, respect, and attention to safety. I can help with babysitting and age-appropriate play/activities (2–10), meal prep / light cooking, light cleaning and tidying up, run errands and helpful tasks around the house. I’m reliable, calm, patient, and caring. I pay attention to details, I communicate clearly, and I take safety seriously. I’m the type of person who shows up on time, follows instructions, and treats your home and your loved ones with respect. If you’re looking for someone dependable and warm to support your child or an older family member, feel free to message me
My name is Jessica, and I’m 28 years old. I have a degree in Early Childhood Education and over six years of experience caring for children of all ages which gave me valuable hands-on experience with child development and daily family routines. I consider myself an active, patient, organized, honest, kind, creative, and loving person. I enjoy spending time outdoors, traveling, and connecting with nature. As a nanny and babysitter, I love planning fun and meaningful activities such as arts and crafts, dancing, painting, board games, nature walks, and more. I truly enjoy supporting children’s growth through playful and engaging experiences. I’m also a native Spanish speaker, and if you’re interested, I’d be happy to introduce your children to the Spanish language through songs, stories, games, and everyday conversation. Currently, I work with a wonderful family with three kids during the week and have been with them for the past two years. They would be happy to provide references. I’m now looking for occasional babysitting opportunities in the evenings and on weekends. I genuinely enjoy spending time with children, helping with bedtime routines, and keeping things tidy and comfortable for families. Thank you for visiting my profile. I look forward to meeting you and your little ones soon!
“Jessica was amazing and helped us feel very comfortable leaving our son in her care. She was prompt and very caring with our one year old who bonded with her immediately!”
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.
Every babysitter on UrbanSitter completes an annual background check, and every profile is individually reviewed by our Trust and Safety team.

"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

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.

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.