
"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 Chestertown. Compare local reviews, rates, and experience to find the right fit.
Looking for jobs? Apply here.
Browse background checked babysitters near you in Chestertown. Compare local reviews, rates, and experience to find the right fit.
Looking for jobs? Apply here.
Families in Chestertown use UrbanSitter for date nights, after school help, and last-minute babysitting.
All babysitters shown here are background checked every year. Learn more.
Hello, hello out there! My name is Sarai (pronounced Sa-rah-eeeee). I’m from Baltimore, MD. Serving the Baltimore-Washington area. Currently at capacity with families.
I am the proud mom of two children (one 28, and one 9). My son is with me 50% of the time, and my daughter is off doing her own thing. I miss the times when they were infants/toddlers, and because of that, this seemed like a great solution to fulfill the desire to still spend time with little ones as well as fill the void when my son isn’t home. I love to do crafts, play outside, and go on adventures (this was my son’s term for when we took trips to the zoo, beach for a day, went on a hike, etc.) I am a veteran of the USAF where I served for 5 years as a Russian linguist. I am bilingual in Russian and English, and have enjoyed teaching my son and daughter’s friends the language over the years. I am extremely patient, and have worked with children that have behavioral issues, and can deal with separation anxiety when their parents leave while the child adjusts to me. Lastly, I am incredibly respectful of parent’s rules, routines and structure. I don’t have the attitude that just because I raised and am in the process of raising my children, that “my way” is best. It also helps that I had a “helpful” (read meddling) mother in law who liked to “impart” her wisdom and knowledge for me to apply to my parenting skills. Thank you for taking the time to view my profile- I hope to hear from you soon! Best, Melissa
Hello, my name is Starla and I am an energetic and fun sitter ! Although I am current law student (3L) , I have 10+ years of experience working with children of all ages. I am also pet friendly.
Hi there! I’m Amanda; a longtime caregiver, former au-pair/nanny, and a single mom of two wonderful kids. Alongside my main work as a consultant, I also serve as a substitute teacher for AACPS, and help coach local kids sports, so I’m used to adapting quickly and connecting with children of all personalities and ages. I work from home most days, which gives me flexibility to help local families with babysitting, after-school care, or date nights. Whether it’s keeping little ones engaged with activities, helping with homework, or making sure evenings run smoothly, I focus on creating a safe, calm, and positive environment where kids feel comfortable. I'm an energetic, dependable, patient, and easy going Australian, and genuinely enjoy being with kids. I’m also happy to lend a hand with light household tasks or pet care when needed. Available for flexible bookings in Edgewater, Annapolis, and nearby areas; open to evening or occasional weekend jobs when my schedule allows.
Hi everyone, my name is Daniah and I’m from Maryland. I’m a recent graduate of Mount St. Mary’s University with a bachelor’s of science in psychology and am currently in graduate school at George Washington University for my master’s in school counseling. I offer child care, senior care, and household services. I have years of experience working with children as a Sabbath School teacher, ABA therapist, and caregiver. I’ve supported kids from toddlers to teens, including children with autism, helping them with communication, daily routines, and social skills. I’m also CPR/First Aid certified. I’ve cared for seniors and vulnerable adults—helping with appointments, errands, medication, and daily support—and love being a steady, compassionate presence. I also assist with cooking, cleaning, and other household tasks. I’m dependable, empathetic, patient, and passionate about helping others feel safe, supported, and cared for. Let me know how I can help your family!
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.
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