Cat Sitting in Chestertown
Book a cat sitter to stop by your home to feed and play with your cat.

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Top rated Chestertown cat sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I have spent my entire life surrounded by animals. From childhood pets to caring for my own senior dogs, animals aren't just a hobby for me—they are family. Most recently, I was the proud "pet parent" to a beautiful Weimaraner for 15 wonderful years. While I’m not quite ready to bring a new dog into my home permanently, I have a surplus of love and care to give, and I miss the daily joy that canine companionship brings. My Daily Routine: Integrated, Flexible Care Pet care isn't just a side task for me; it’s a seamless part of my family’s daily life. While I work full-time, I am fortunate to have a highly flexible schedule. My office is located nearby, which allows me to be "on-call" for my furry guests throughout the day. A Typical Day Includes: Morning Kick-off: We start the day with a potty break and some fresh air in my fully fenced yard before I head to the office. Midday Check-ins: I prioritize dropping back home (or to your home) during my lunch break for potty breaks, midday walks, and plenty of head scratches. This ensures no pet goes too long without a stretch and some affection. Afternoon Enrichment: After work, the real fun begins! We spend time outdoors watching the chickens (our favorite "Chicken TV") or playing in the yard with my two young children. Evening Wind-down: Evenings are for relaxing. Whether I’m doing an overnight stay at your place or hosting at mine, your pet will have constant companionship, evening walks, and plenty of couch cuddles. Because of my proximity to home and my flexible hours, your pet will never feel lonely. I prioritize quality time and active engagement during every visit, ensuring they feel like a true member of the family while you're away. Supervised Socialization With two young children (ages 5 and 6) who adore animals, safety is my absolute top priority. My children have been raised to respect a dog’s boundaries, understanding "dog language" like when a pup needs space or is finished playing. All interactions between my children and your pet are 100% supervised to ensure a positive, stress-free experience for everyone. Secure Physical Boundaries My home is set up for safety and peace of mind: The Yard: I have a fully fenced-in backyard where dogs can run freely and securely. The Chicken Safety Zone: My chickens are kept in a separate, double-fenced area. This allows dogs to enjoy the mental stimulation of watching the birds ("Chicken TV!") without any risk of physical contact or prey-drive incidents. Indoor Retreats: I maintain dedicated "quiet zones" where your pet can go if they need a break from the family action. Whether it’s their crate or a specific cozy corner, I ensure they have a place that is off-limits to the kids. Experienced Oversight Having cared for a Weimaraner for 15 years, I am highly attuned to a dog's subtle cues. I work full-time but have the flexibility to be home frequently throughout the day, ensuring the yard is supervised and everyone is following the "house rules." I treat your pet’s safety with the same level of seriousness I apply to my own children’s.
About: I grew up surrounding myself with animals, since I was seven I spent all of my time at our horse farm and I learned to take care of animals big and small. This grew into my life passion which is animals. I studied animal science at UMASS Amherst and UNLV and also have worked at various animal clinics with different roles as a kennel technician and a veterinarian assistant learning so many skills along the way. Yet my favorite thing I have done so far is taking care of animals while their families enjoy a vacation away! It takes the stress out of going to the kennel, the animals get to show me the ropes and the owners always have daily updates and pictures! I currently work part time at a local restaurant, and my shifts are typically mid afternoon to the evening, but I am flexible upon request!! I am more comfortable coming to a clients home. I own two cats and unfortunately do not have a fenced in yard. But there are parks around my neighborhood that are great for walks.
“This was our first time leaving Buddy under the care of Brandy and she did great. I received photos of him and never had to worry that he wasn't being cared for. I would highly recommend her.”

“Emily was the closest Rover sitter to me in a remote location, put she was still about 20 minutes away. She stopped by AFTER a full days work, which was at least another 20 minutes in the opposite direction from me. Despite these logistics, Emily showed up consistently early evening immediately after her work day. She performed all the duties necessary during each visit, plus she performed some special handling for a package that arrived while I was away. I would not hesitate using her again, and would recommend her.”

“Jaimi dropped in with little notice to take care of our dog. She stayed longer than necessary and gave Colden lots of love. I would definitely recommend and will request her again.”

About: Common courtesy and communication is paramount. **Willing to travel up to an hour away. Just because Rover says you are outside my service area it does not always mean you are. I have clients an hour North and South of me. **Necessary update as of 6/21/23** I will require current credit card info be on file at your vet or provided for me in your pet write up ONLY in case of emergency. In the event of an emergency and I could not get a hold of the human, puppies have no pockets to hold a card, the vet required me to pay. I have raised 3 separate RESCUE Rottweilers to be exceptional ambassadors of their breed. I currently do not have any pets since my big boy passed away in 2016. I hope to again one day have my own dogs. Until then I will love YOUR pet. **I DO NOT board animals at my home. Only repeat clients would MAYBE be possible for a very short amount of time.** Clients pets have included many breeds, species for days, weeks. Many Golden Retrievers, Doodles, mixes aka Heinz57s, Old English Sheep dog, lots of kitties, a chameleon, turtles, a bearded dragon, a small bird, fish, Rottweilers, a very challenging but lovable English Bulldog and Huskies one of which was very reactive. Oh and a LOT of house plants! PLEASE NOTE: I am deathly allergic to horses which I am very sad about. Any type of animal requiring LARGE amounts of hay would also be a problem i.e, goats, cows, alpacas I am sorry to say. Small rodent animals requiring hay for food or bedding has not been a big deal. My personnel dogs were very public dogs, parks, events etc. With the ever present fact in mind that as good as my animal was it is still an animal. Never purposely putting them in a situation to be loose (unless at home or a fenced park) or get into anything that could harm them. Read quite a few books/manuals by military working dog trainers in hopes of training a service oriented Rottie. Came very close to passing the Good Citizen certification but my dogs never liked the “stay” part when I had to walk away with my back turned. They just had to be next to me. So close. PLEASE NOTE: I have my preferences set to NOT to show any photos of YOUR pet publicly. I would ask permission first to share. Photos only NEVER infomation of course. My schedule allows me to be available to be in YOUR HOME, with your pets all day/night, unless noted ahead of time and of course trips to the store. I have many types of animals that insist on sleeping in bed just like they do when their people are home which in fine by me. Just take some Benadryl and snuggle on in. I try to stick closely to how the home runs normally so the pets do not have any surprises that can make them anxious. Sleep, food, walks, play time etc. I supervise dogs in their own yard fenced or not. I am very organized and like an outlined idea of their schedule to be written down for me to follow as closely as YOU would.
How Rover works

1. Search
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2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your cat while you’re away
3. Book & Pay
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Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your cat sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total cat fanatics. You can get in touch with us anytime.
Cat Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple cat sitters about your booking. Typically, cat sitters on Rover respond in under an hour.
Experience can vary widely from cat sitter to cat sitter, but you can view reviews, years of experience, and number of repeat clients when comparing cat sitters available in Chestertown.
Do you simply need someone to stop by and play, feed, and scoop? Chestertown cat sitters are happy to take care of your cat while you’re at work, on vacation, or unavailable for the day, even if all you need is a quick drop-in! Your cat sitter will stop by to feed, play with, and snuggle your cat as many times a day as you like. And the best part? Your cat gets to stay on their home turf.
Yes! Cat sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your cat sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your cat sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your cat is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your cat sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your cat sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your cat sitter’s cancellation policy.






