Cat Sitting Chestertown

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Over 44
pet parents in Chestertown have booked cat sitting

Chestertown, Find top rated cat sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Marissa F.
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Marissa F.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
49 reviews
14 repeat clients
15 years of experience
Chestertown, MD, 21620

Marissa is the best cat sitter EVER. She is thoughtful and respectful of my cats, myself, and our home. She understands each of my cats’ needs and caters to them as individuals. She even proactively alerted me when the food supply was getting low so I could order more while I was away. She also accommodated my needs when I had to change my flight home and agreed to extend her services for more days. She’s my favorite!!!

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Holly P.
Sitter Profile Image: Elaine P.
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Elaine P.
from
$20
per visit
5.0 out of 5 stars
20 reviews
7 repeat clients
20 years of experience
Chestertown, MD, 21620

Elaine was amazing with my two dogs while I was out of town, she sent lots of photos and made sure they were well taken care of and having fun, it made my trip so much better with all of the updates!

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Sarah S.
Sitter Profile Image: Sabrina G.
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Sabrina G.
from
$25
per visit
4.6 out of 5 stars
32 reviews
9 repeat clients
15 years of experience
Chestertown, MD, 21620

Sabrina did a great job taking care of our three cats and chickens. She sent daily updates and pictures. We will definitely be using her as a pet sitter again!

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Chelsea P.
Sitter Profile Image: Crystal D.
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Crystal D.
from
$15
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
17 years of experience
Ridgely, MD, 21660

Couldn’t be more flexible and a bigger help.

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Ken S.
Sitter Profile Image: Liliana O.
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Liliana O.
from
$35
per visit
5.0 out of 5 stars
16 reviews
2 repeat clients
10 years of experience
Chestertown, MD, 21620

About: I have been around animals my whole life; owning, house sitting, and walking. I have pet sat all different ages of animals, mainly dogs, since I was young. I am a very active person! I’m currently an assistant basketball coach. While I am busy during the days, I do have a lunch break to give your animal love. But after the day, my time is spent with your pet giving them all the love and exercise they need! The pet(s) are the main priority, so their needs with be met swiftly. I also maintain a very organized, clean area that I stay in.

Sitter Profile Image: Ashley C.
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Ashley C.
from
$28
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
10 years of experience
Centreville, MD, 21617

About: I’ve been dog walking and sitting for neighbors since I was 12 years old. I’ve dog sat multiple types of dogs. I’ve done dog walking, check-in & potty break visits, and I’ve stayed at a clients home for long periods of time (5+ days) to be with their pups. I’ve also been tasked with administering insulin shots to dogs before. And I have a lot of experience with dogs that have anxiety, whether with new people, thunderstorms, or anything else, as I have one myself and a long remaining client of mine does as well. I’ve always loved dogs, having grown up having 2 smaller dogs myself. I am hoping to do pet sitting as a new permanent business, so I will have nothing but time to look after your pets! I will schedule out days and time periods based on client necessity and to provide the optimal care for your pets. Because I have two dogs myself, one of which has severe people and other animal anxiety, which for the safety of your pets and mine means I am unable to bring any pets into my home as of current. However, I’ve stayed at the homes of clients before to be with their pups while they’re away. I feed them every morning and night or make sure the food bowl is full depending on how the client feeds their dogs. I give them any medicine or joint tablets that they need to be well. I let them out multiple times a day whenever they need it. And I try to play with and pet them as much as I can while I’m there so they don’t miss their humans too much. I will even take them on a walk if allowed.

Sitter Profile Image: maranda c.
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maranda c.
from
$22
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
10 years of experience
Centreville, MD, 21617

Fantastic job with taking care of our pets. She took some of the best pictures and kept us thoroughly updated. We would happily use her again.

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Justin A.
Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$30
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
4 years of experience
Centreville, MD, 21617

About: As a CPDT-KA certified trainer, I offer dog walking services that go beyond basic exercise. Each walk incorporates training and enrichment tailored to your dog’s unique needs. My expertise is ideal for dogs who are fearful, nervous, hyper, or reactive—especially those other walkers may find challenging. A training walk is a perfect way to advance your dog’s progress when your schedule is too packed for regular training sessions. Please note: My walking services are not suitable for aggressive dogs. If you’re dealing with aggression, please contact me directly or explore my specialized training services. I offer training walk services Monday through Friday, with both daytime and evening availability. For the best results, I recommend scheduling two sessions per week, such as Monday/Tuesday or Wednesday/Thursday. I exclusively use positive reinforcement techniques to care for and train dogs, whether during training walks or in your home. My focus is on creating a safe, encouraging environment that builds trust and confidence in your dog. Each session is tailored to meet your dog’s unique needs while reinforcing good behaviors in a kind and effective way. With this approach, I ensure your dog feels supported and thrives in their routine.

Sitter Profile Image: Heather B.
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Heather B.
from
$35
per visit
5.0 out of 5 stars
35 reviews
14 repeat clients
18 years of experience
Wilmington, DE, 19803

Thanks Heather for taking such great care of Moxie and Stella last night!

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Stefanie B.
Sitter Profile Image: Chris M.
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Chris M.
Star Sitter
from
$38
per visit
5.0 out of 5 stars
65 reviews
20 repeat clients
50 years of experience
Wilmington, DE, 19809

This is the second time Chris has watched our dogs and we're so grateful. She is attentive and punctual with excellent communication. She is our new go-to!

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Jessica W.
Sitter Profile Image: Paul C.
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Paul C.
from
$20
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Elkton, MD, 21921

Love the photos! This was our first time using anyone for a pop in visit. This was totally last minute! Asked Paul and his fiance last night at 7pm to please help us, and without hesitation they came right over and met our boys. They did a pop in visit today and they were wonderful!!! Will definitely use them again :) They were great!!!! Thank you both so much !

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Leanna
Sitter Profile Image: Elizabeth W.
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Elizabeth W.
from
$35
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
13 years of experience
Centreville, MD, 21617

Elizabeth did a great job taking Zuma on his walks and keeping us posted on everything including sending pictures! We highly recommend Elizabeth for your pet care needs!

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John & Sherri T.
Sitter Profile Image: Krista K.
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Krista K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
10 years of experience
Camden, DE, 19934

About: Over the past several months, I've had the pleasure of caring for dogs and cats of all ages, from energetic puppies to sweet senior companions. Every pet has their own unique personality and routine, and I take the time to make sure they feel safe, comfortable, and loved while you're away. I have experience administering medications to senior dogs and understand the importance of following care instructions carefully and consistently. Whether it's sticking to feeding schedules, giving medications, going for walks, or simply providing companionship, I treat every pet as if they were my own. When I house sit, I also take great pride in caring for your home. I always aim to leave it cleaner than I found it, so you can come home to happy pets and a tidy, well-cared-for space. My goal is to give you complete peace of mind, knowing both your furry family members and your home are in caring, reliable hands. Caring for animals is already woven into my daily rhythm. I work part-time with flexible hours, giving me plenty of space in my schedule for peaceful walks, playtime, and check-ins with pets. I’m used to creating a balanced routine around my own dog, and bringing that same calm, attentive energy to other pets feels completely natural. I am currently free to sit/walk any day of the week as well as house sit for as long as you need. When caring for pets in a client’s home, I focus on creating a safe, calm, and familiar environment for them. I follow your routines exactly as you outline them — from feeding instructions to walk times to any training cues your dog is used to. I keep doors and gates secured, monitor their body language closely, and make sure they always have fresh water and a comfortable space to relax. Trust is extremely important to me, so I communicate clearly, send updates/photos, and treat your home with the same respect and care I treat your pet.

Sitter Profile Image: Chloe T.
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Chloe T.
from
$32
per visit
4.9 out of 5 stars
15 reviews
2 repeat clients
17 years of experience
Easton, MD, 21601

Chloe was a great sitter for my cat Melody! Her reports have me peace of mind while out of town and I loved getting photos of my baby. Would book with Chloe again!

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Allison F.
Sitter Profile Image: Ciara A.
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Ciara A.
from
$39
per visit
4.5 out of 5 stars
10 reviews
2 repeat clients
8 years of experience
Middletown, DE, 19709

Ciara was pleasant from the first meet. Thanks for caring for our fur baby while we were away. Thanks for the constant updates.

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Indolicia S.
Sitter Profile Image: Jordan M.
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Jordan M.
from
$20
per visit
4 years of experience
Smyrna, DE, 19977

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!

Sitter Profile Image: Josiah S.
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Josiah S.
from
$10
per visit
3.0 out of 5 stars
2 reviews
12 years of experience
Centreville, MD, 21617

About: I will love and take care of your pets as if they were my own. I love to go out and play with pets I care for. I would dog sit when I was in high school for different families. Those families loved how attentive I was, and as a result they would refer me to their friends. I’m always available for you buddies! You and me both know that your pets are more than pets, theyre family. You don’t want just anyone taking care of family. I do currently work full time, however I have a job that is extremely flexible. I set my own hours, including when I am in my office. This pairs perfectly with animal care and house care because I can come and go as frequently as needed. Due to my open schedule I can be available for any needs your pets may have. I prefer to let the client tell me exactly what they want for their pet. I like to keep your life as simple as possible while giving you peace of mind by following any requests you have. If you need your animal crated, if you want them roaming, whatever is asked you can expect to be done.

Sitter Profile Image: Aaron W.
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Aaron W.
from
$19
per visit
25 years of experience
Worton, MD, 21678

About: I have lots of compassion when it comes to animals, and I have years of experience working for cat/dog rescues as well as pet transports, I currently have a four day weekend at my current job and have way too much free time! I also have no problem with early mornings or late nights! I have two small dogs that I take for a couple walks a day, and I Help prepare their food which is home made and all natural. I also have a cat with urinary tract issues so I’m used to keeping their litter boxes spotless.

Sitter Profile Image: Courtney W.
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Courtney W.
from
$30
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Townsend, DE, 19734

About: Hey, I’m Courtney, a passionate animal lover with hands on experience in veterinary care and a deep commitment to keeping pets happy, safe, and loved. I’m a recent graduate from Delaware State University and I work as a Veterinary Assistant at a local animal hospital in Middletown, DE. Over the years, I’ve cared for dogs of all sizes and personalities from cuddly to high energy. My experience includes everything from administering medications, handing emergencies, senior and puppy care,daily walks, playtime, and providing lots of belly rubs! Whether you’re looking for drop in, dog walking or overnight care, I bring professional compassionate care tailored to your pet’s needs. I treat every dog like family because that’s what they deserve. Let me know how I can help give you peace of mind while you’re away. I’m excited to meet your furry friend. Im working full time as a veterinary assistant, but I’m still available to your pet depending on your needs morning or nights to play with them and give them care. I have an extra crate at home. In clients home I like to establish trust and bonding with pets. Maintain a routine if any for the pet and provide good stimulation.

Sitter Profile Image: Kayla J.
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Kayla J.
from
$30
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Milford, DE, 19963

Kayla was great! Muffin was well taken care of, pictures were adorable, and peace of mind was priceless. I would definitely recommend Kayla to care for your pet and have her care for Muffin again. Thanks Kayla!!❤️

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Dawn M.
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The median cost per visit for cat sitting in Chestertown is $20

Cat parents share their Rover experiences - Chestertown

1 / 1
5.0 out of 5 stars

Sabrina did a great job with our 22 year old cat, even spending extra time with her. Her many pics each day made leaving her alone for the week much more bearable. She paid close attention to our girl and informed us of anything that changed. We will definitely use her in the future.

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Calvin D.
Drop-In Visits
5.0 out of 5 stars

Sabrina did a great job taking care of our three cats and chickens. She sent daily updates and pictures. We will definitely be using her as a pet sitter again!

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Chelsea P.
Drop-In Visits
5.0 out of 5 stars

Shaun was wonderful with our 22-year-old cat, Gizmo, over the Christmas holiday. He’s watched her several times now, and she consistently responds so well to him—something that means everything to us given her age. We have complete peace of mind when he’s caring for Gizmo and will absolutely continue booking with him. Highly recommend!

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Calvin D.
Drop-In Visits
1 / 1
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Sitters in Chestertown average 7
repeat cat sitting clients

FAQs for Drop-In Visits - Chestertown

Frequently asked questions about Rover

The average cost for Cat Sitting in Chestertown on Rover is $21.4 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Cat Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Cat Sitting. For more information on service fees, click here .

As of August 2026, there are 1,770 sitters on Rover offering Cat Sitting across Chestertown. Enter your ZIP code to see which available sitters are closest to your home.

Cat sitters on Rover care for your cats’ needs and can spend quality time with them, including activities like feeding, playing, and refreshing their water and litter boxes. Depending on your arrangement, you can schedule as many visits per day as your cat needs or find a sitter who can stay at your house overnight. Some sitters also board cats in their home.

House sitting can be ideal for cats who need socialization or care that lasts longer than a few hours. Your cat stays in their own home, on their own schedule, with care based on what you and your sitter agree on together.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your cat, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Yes, you can find sitters who have experience with handling special pet needs in Chestertown. On Rover:

  • 94% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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