Pet Sitting in Chestertown
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Chestertown pet sitters

About: Animals have been part of my life for as long as I can remember. As a kid, I cared for hamsters, fish, and even a little parakeet. At 19, I adopted Max, a sweet lab mix who became my constant travel companion for 11 wonderful years as we explored the East Coast together. I’ve raised all my dogs from puppyhood, giving me plenty of experience with training, socializing, and caring for them through every stage of life. Today, my family and I live on 220 beautiful acres in Chestertown with: Beauty – Aussie Heeler mix (5) Scooby – lovable mutt (2) Yakko & Dot – tuxedo cats (3) 70+ chickens with big personalities A lively 55-gallon aquarium with community fish and snails, which has taught me the importance of maintaining delicate habitats Living with so many animals — from dogs and cats to chickens and aquarium life — has taught me patience, adaptability, and the joy of connecting with creatures of all kinds. Whether it’s walking a high-energy dog, keeping a shy cat comfortable, or caring for fish and poultry, I treat every animal like they’re part of my family. I split my time between Chestertown and Glens Falls, which means I can offer flexible pet care in both areas. I’m available for drop-in visits in Glens Falls on the days I’m there, as well as home stays in either location. I’m currently recovering from a car accident and walk with a cane, so while I can’t take dogs on long walks, I can safely let them out into a fenced yard or supervise them on a lead. At this time, I’m not offering boarding services in my own home, but I do plan to in the future. For now, my focus is on providing reliable, in-home care and check-ins so your pets can stay comfortable in their familiar environment. Whether I’m caring for pets in my home or in yours, their safety and comfort always come first. In your home, I follow your routines closely — from feeding schedules to favorite playtime activities — so pets feel secure in their familiar space. I make sure doors and gates are secure, keep an eye on water and food bowls, and provide supervised outdoor time in fenced areas or on a lead. In my home (for future boarding services), pets will enjoy a calm, animal-friendly environment on our 220-acre property, safely separated from my own animals as needed. I have experience managing dogs, cats, poultry, and aquarium life, which means I’m attentive to different needs and personalities. As a volunteer firefighter here in Chestertown, safety and responsibility are part of my everyday life. I also believe trust is built through clear communication — you can expect regular updates, photos, and honest feedback while your pets are in my care.

About: I have three dogs at home myself and love caring for them. I’ve previously worked at a dog daycare for a couple years and learned dog body language administering some medications and giving baths. I can help with feeding, providing exercise, bathing, administering medication, and ensuring that your animal with be safe and comfortable. I currently work part time and have flexibility with my current job that allows me to help care for your pet!! I am very flexible with days and times I will be needed to care for your pet. I have a big back yard for your dog to get it’s daily exercise I have three other dogs in my home to keep yours company!!

“I reached out to Brittney at the last minute one evening and needed someone for the next day. She was great and responded quick to help out. She treated my dog amazing and would definitely recommend and will be reaching out to her again! Thank you!!”


About: I have always loved animals and I have my own as well. I take care of my senior pup along with caring for friends and families pets as well. Always a good time with extra love to give. Reliable and fun. I work five days a week at a marina however, I am always open at night and on my days off I am more than happy to care for your animals. To care for my own pet I take him out multiple times a day, I walk him, feed him, bathe him, and so much more but with other animals it varies, depending on the instructions given by the owner is what I will do along with extra love.

About: Hello! My name is Kaleigh. I’m twenty one years old, and I absolutely adore every fur baby around. It doesn’t matter what animal it is, I love all. I have always been surrounded by guinea pigs, hamsters, chinchillas, birds even. I owned a lot of chickens growing up, only for eggs, and i’ve had so many pups to spend my time with. I have a chihuahua who is a certified service animal, as I am diagnosed with epilepsy. I am medicated for that and all seems well. My boyfriend lives with me and typically comes if I take care of pets, but I can make arrangements if needed, just isn’t preferred because it’s a lot easier for the ride factor. I love to write poetry, make music, I draw frequently, and I went to a technical school for culinary as well. Thank you for reading about me. I currently do not have a full time job. I have worked prior at a camp that helped disabled people and nourishes them in the ways they deserve. I’m a stay at home and I help my mom & dad with my dogs and cats, but i’m free any day of the week, as long as it’s known a day ahead, but I would also take emergencies. I have a fenced in yard, but it’s big enough to where my dogs are able to explore around the yard and look through, so they’re still living their best lives. My chihuahua loves to sit on our porch, it’s the first place she runs to in the morning to lay in the sun. She also loves going on rides and exploring the world, going on adventures.

“We just moved to a new area and our dogs were a little anxious, but we unfortunately had a wedding to attend and needed a sitter. Jaimi was great with our two dogs, sending lots of photos, and even looked after our chickens! Our dogs warmed up to her right away. I will definitely be asking Jaimi to dogsit again in the future!”


“Kim cat sit for my 2 cats while I was on vacation. Her fees were quite reasonable. She did all I asked to take care of my kitties, and went the extra step of cleaning up after they vomited. She expressed some concern regarding this and my cats health, as it was a few days running. It was likely caused by some factors that were out of her control (e.g., eating dried out wet food that probably wasn't good anymore). One cat is prone to throwing up - she will go weeks without throwing up, and then throw up daily (sometimes multiple times a day) for a few days. Due to an injury, I returned home earlier than expected. Kim helped get a partial refund from Rover for the days that went unused. Overall, I was quite happy with Kim. I took away one star, as it appears she forgot to give them fresh water on the last day.”


“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.”



About: I love all animals, I do have experience with medication administration, or reactive types of dogs. I am experienced in senior care or helping in training puppies while I care for your pets I currently work per-diem, and attend school full time. I have weekends free and evenings and always free to pop in most times especially overnights. My pup sleeps with me, he is spoiled like my own child. All my animals are well cared for and happy. I am comfortable stopping in for checkups or walks or even overnight stays

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.

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.

About: I’ve had 15 + years working in animal rescue and have always had dogs and cats from childhood. My pets are my babies and I’d love to provide the same care yours in their own space when you have to be away. I currently work from home with a very flexible schedule so it’s easy for me to adjust to provide for your pets comfort with multiple visits as needed.. I can provide multiple short walks or one long one. My own dogs love a 1.5 hour mid day hike which we can include your dog on if he/she is friendly with others.

“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.”


About: Over the last 7 years I have worked for many veterinary hospitals, including general practice and emergency medicine. With an associates degree in veterinary science, I’m well rounded to meet the needs of your fur babies! Working with animals Is what I love to do. Do you have special medical needs for your pet? No problem! I am very experienced with all forms of medications. Working for two veterinary hospitals, medicating animals is a daily need to know skill! Have a high energy pup that loves the outdoors? Rest assure they will be tired after some fun play time outside! I am very active and would love to bring your pup for a walk around the block/trails/dog park or play ball in the backyard! Need someone to stop by while you’re gone? I’m a great comfort friend and would love to help pass the time with your pet while you’re out for the day! I'm also very accommodating to those pets that may have more specific requests (anxious, does not like other dogs, food aggression, behavioral concerns, etc) I want to make sure each pet has fun but is also safe! I’d be happy to stop by before and after work (7am-5pm). I am fully available on Friday, Saturday and Sunday's. Of course I can accommodate and work around schedules as well. Small fenced in back yard along with daily walks over 30 minutes. Just a short drive away from multiple trails / parks in the area!

About: Friends and family have relied on me to walk & check in on their pups for years, and now I want to extend my services! I’m currently working part time which gives me a flexible schedule to accommodate clients on a basis that best works for them. Whether it be a drop in or long walk, my availability gives me the opportunity to help make sure your dog is happy as can be. Due to my experience with dogs over the years, I’m able to meet most requests while also providing a trusting relationship & safe environment for your pup.

About: Hello there, my name is Riley and i love pets of all shapes and sizes, big, small you name it. i have a ton of experience pet sitting and would be more than happy to dog sit in your home and stay there as needed also willing to do drop ins to feed and water. I also do walks around your neighborhood as well if needed. i am a honest, hardworking and trustworthy person and i will treat your pets as if they were my own, because really isn't that what every pet owner wants? to know that their pets are taken care of and loved when they are away for long periods of time or just for the day while your at work. I always make time for clients and there pets no matter what. I will treat your dog as my own, and i am available 24/7. I always listen to instructions and follow them to a T, always make sure everything is locked up when I leave and the dogs are in crates if you crate them.
Loving pet sitters in your neighborhood
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Jonathan F.
“Jonathan and his partner Michaela are great people that love animals. They watch our German Shepherd and we never find that Tonka is lonely when we are gone. You can tell how much they love them because when they see each other he would spend more time with them than me!”


Miranda C.
“Miranda did a fabulous job watching our dog rocky!! She was great with communicating with us. She kept us updated and sent pictures of our puppy during the time we were gone from home. She’s proven she is reliable and trustworthy.”


Brittney R.Star Sitter

“I reached out to Brittney at the last minute one evening and needed someone for the next day. She was great and responded quick to help out. She treated my dog amazing and would definitely recommend and will be reaching out to her again! Thank you!!”


Bianca D.
“I have had the privilege of knowing Bianca for over a year, and in that time, she has consistently demonstrated qualities that speak to her outstanding character. She is one of the most responsible, dependable, and compassionate individuals I have ever met. Whether in everyday situations or moments of real need, Bianca is always the first to offer help, often putting others before herself without hesitation. Her sense of responsibility is evident in everything she does she follows through on her commitments, handles challenges with maturity, and maintains a calm and thoughtful demeanor even under pressure. I have personally relied on her many times, and she has never failed to be there with sound judgment, a positive attitude, and genuine care.”


kaleigh f.
About: Hello! My name is Kaleigh. I’m twenty one years old, and I absolutely adore every fur baby around. It doesn’t matter what animal it is, I love all. I have always been surrounded by guinea pigs, hamsters, chinchillas, birds even. I owned a lot of chickens growing up, only for eggs, and i’ve had so many pups to spend my time with. I have a chihuahua who is a certified service animal, as I am diagnosed with epilepsy. I am medicated for that and all seems well. My boyfriend lives with me and typically comes if I take care of pets, but I can make arrangements if needed, just isn’t preferred because it’s a lot easier for the ride factor. I love to write poetry, make music, I draw frequently, and I went to a technical school for culinary as well. Thank you for reading about me. I currently do not have a full time job. I have worked prior at a camp that helped disabled people and nourishes them in the ways they deserve. I’m a stay at home and I help my mom & dad with my dogs and cats, but i’m free any day of the week, as long as it’s known a day ahead, but I would also take emergencies. I have a fenced in yard, but it’s big enough to where my dogs are able to explore around the yard and look through, so they’re still living their best lives. My chihuahua loves to sit on our porch, it’s the first place she runs to in the morning to lay in the sun. She also loves going on rides and exploring the world, going on adventures.


Jaimi V.

“We just moved to a new area and our dogs were a little anxious, but we unfortunately had a wedding to attend and needed a sitter. Jaimi was great with our two dogs, sending lots of photos, and even looked after our chickens! Our dogs warmed up to her right away. I will definitely be asking Jaimi to dogsit again in the future!”


Kim M.

“Kim cat sit for my 2 cats while I was on vacation. Her fees were quite reasonable. She did all I asked to take care of my kitties, and went the extra step of cleaning up after they vomited. She expressed some concern regarding this and my cats health, as it was a few days running. It was likely caused by some factors that were out of her control (e.g., eating dried out wet food that probably wasn't good anymore). One cat is prone to throwing up - she will go weeks without throwing up, and then throw up daily (sometimes multiple times a day) for a few days. Due to an injury, I returned home earlier than expected. Kim helped get a partial refund from Rover for the days that went unused. Overall, I was quite happy with Kim. I took away one star, as it appears she forgot to give them fresh water on the last day.”


Emily P.

“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.”


Karen W.

“Karen was fantastic! My pup was quite the handful (first time) & she was so patient & knowledgeable & really went the extra mile above & beyond. Highly recommend!”




Andrea N.
About: I love all animals, I do have experience with medication administration, or reactive types of dogs. I am experienced in senior care or helping in training puppies while I care for your pets I currently work per-diem, and attend school full time. I have weekends free and evenings and always free to pop in most times especially overnights. My pup sleeps with me, he is spoiled like my own child. All my animals are well cared for and happy. I am comfortable stopping in for checkups or walks or even overnight stays




Colleen D.

“Thank you for coming to take care of them with such short notice! We are up here at least one e a month and will be rebooking g and referring to our friends.”


Jennifer F.
“Jennifer took care of our 8-month-old Havanese puppy this past summer for the week we were away. She stayed with him the whole time and he was SO happy. We know because she sent pictures every day and he was showing her love the same ways he shows us. We already have her booked for next year! She is dependable and trustworthy, and I would recommend her to anyone.”


Alissa V.

“She’s the best! Whit and Larry love her.”


Jessica L.
“I had Jessica watch my beautiful Australian Shepard Maiya. She was kind, sweet and gave her tons of loving. I would recommend her to watch anyone fur baby!”


Ann H.
About: I’ve had 15 + years working in animal rescue and have always had dogs and cats from childhood. My pets are my babies and I’d love to provide the same care yours in their own space when you have to be away. I currently work from home with a very flexible schedule so it’s easy for me to adjust to provide for your pets comfort with multiple visits as needed.. I can provide multiple short walks or one long one. My own dogs love a 1.5 hour mid day hike which we can include your dog on if he/she is friendly with others.


Caitlyn A.

“Caitlyn was friendly and dependable. She provided regular updates while we were away. Would definitely have her take care of our pet again.”


Brandy L.

“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.”


Rianne P.
“We were so happy with this dog sitting business!!!! I was so nervous to leave my 2 dogs for the first time for a week, but soon was at ease .... I got happy puppy pictures and update messages every day and they had wonderful walks and I came home to 2 very happy puppies. Would recommend 100% and I will be reaching out for services again for September!!!!!”


Taylor F.
“Taylor went above and beyond for my slightly reactive dog. When I expressed my concerns and our daily patterns, Taylor took exceptional notes and was sure to be careful, help train our dog & send me daily updates with pictures. I highly recommend Taylor for anyone that needs a responsible, trustworthy and smart caregiver.”


Riley S.
“Riley has watched my dogs before and he is great, he made sure they were fed and watered everyday, walked and exercised and gave them lots of love and attention as if they were his own.”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Chestertown on Rover as of Aug 2025 was about $25 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 22 pet sitters in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 100% of Chestertown pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Chestertown.
Rover makes it easy to find Chestertown pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 22 pet sitters in Chestertown on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
