Find a babysitter in Chestertown, MD

Browse background checked babysitters near you in Chestertown. Compare local reviews, rates, and experience to find the right fit.

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9 available babysitters in Chestertown, MD

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.

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Sarai
Booked by 1 repeat family
1 review
Dundalk
$8 per hour for 1 child
Booked by 1 family in Chestertown, MD

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.

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Melissa Annapolis
$20 per hour for 1 child

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

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Starla
Booked by 5 repeat families
4 reviews
Baltimore
$23 per hour for 1 child
Booked by 9 families in Chestertown, MD

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.

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Amanda Edgewater
$22 per hour for 1 child
Booked by 1 family in Chestertown, MD

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.

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Caroline Severn
$28 per hour for 1 child

I have a wealth of experience working with children, spanning from my hometown to my current role as a nanny for two spirited children. My background encompasses caring for children of all ages, from newborns to teenagers. I pride myself on being patient, adaptable, and nurturing while maintaining strong organizational skills. I understand that caring for children can be challenging, but I always strive to meet the unique needs of each family. I am passionate about fostering creativity through screen-free activities such as music, dance, and arts and crafts, ensuring a fun and enriching environment. Additionally, I have a clean driving record, my own vehicle, and hold certifications in CPR and first aid, giving you peace of mind when it comes to your children's safety and well-being.

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Recent babysitter activity in Chestertown, MD

Trust and safety come first

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.

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"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

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"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

photo of quoted parent Laura

"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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Frequently asked questions about Chestertown babysitters

What does a babysitter do?

Babysitters supervise children and keep them safe while you're away. Depending on your needs, they may also help with meals, bedtime, homework, light cleanup, school pickup, or activities.

How do I find a babysitter near me?

Sign up for a free UrbanSitter account, post a job with your dates and needs, and review babysitter profiles, including distance, before choosing the right fit. Learn more about how UrbanSitter works.

Are babysitters on UrbanSitter background checked?

Yes. Every Chestertown babysitter on UrbanSitter is background checked annually, and each profile is individually reviewed by a trained specialist on our Trust & Safety team. Learn more about what's included in a background check.

What's the best way to find a last-minute babysitter in Chestertown?

Sign up for a free UrbanSitter account, then request a babysitter by posting a job with your needs. In most cities, sitters will reply within minutes, so you can review choices quickly, then book them immediately.

Can I find babysitters for after school care in Chestertown?

Yes. Families often use UrbanSitter for after school care, including pickup, homework help, tutoring, and early evening coverage. You can filter for babysitters who are willing to drive or have their own car.

Can I find babysitters for evenings, weekends, or extended hours in Chestertown?

Yes. Families in Chestertown use UrbanSitter for date nights, weekend plans, extended hours, and other scheduling needs. You can review each sitter's availability and experience to find someone who fits your hours.

Resources

The Ultimate Babysitter Guide for Parents

A step-by-step guide to hiring the right babysitter.

Tips for Finding Last-Minute Child Care

How to find a babysitter fast when plans change.

Top 20 Questions to Ask a Babysitter in an Interview

Essential questions to help you find a great fit.

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