Dog Walkers in Chestertown, NY
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Chestertown dog walkers

About: I have had pets my whole life. I currently have a small farm. I have chickens, ducks, turkies, pigs, dogs and cats. Alone with rabbits and guinea pigs. we are a very pet friendly area. Live in a wooded area on a dead end street. I currently work from home and have time for pet care. My youngest daughter is also in the home. Also have my granddaughter here on the weekends. she is 11. I will provide care in my home since I work from home this is the best for me at this time. I also have my 11 yr old granddaughter here on weekends.

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.

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!!

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: What sets me apart as a sitter is my genuine love and passion for taking care of animals. I have extensive experience in puppy care, which includes basic obedience and potty training. Additionally, I have specialized knowledge in providing senior care for pets, ensuring their comfort and well-being. I believe in creating a safe and nurturing environment for all animals under my care. Let me know if you have any specific questions or if there's anything else I can help you with! Pet care is an important part of my daily and weekly routine. I make sure to allocate dedicated time each day to feed, exercise, and provide attention to the pets I care for. I also prioritize regular check-ins and updates with the owners to keep them informed about their furry friends. It's all about creating a structured and loving routine that ensures the well-being and happiness of the pets in my care. When caring for pets in my home, I ensure a safe and comfortable environment. When caring for pets in the client's home, I aim to maintain a familiar and consistent environment for the pets. I follow their regular routines as closely as possible while making sure to keep their living areas clean and tidy. Ultimately, whether in my home or the client's home, my goal is to provide the best care possible, ensuring the pets feel loved, safe, and comfortable. Let me know if you have any more questions or if there's anything else I can assist you with!

About: I’ve had dogs my whole life. Recently I worked at a Doggy Day Care where I ensured the safety of over 20 dogs by myself at a given time. I promise to love and take care of your dog like they were my own Open schedule. Weekends and weekdays acceptable. Overnights, one dog at a time. My focus will be solely on your dog. Plenty of potty breaks and fun I always make sure to follow an owners instructions on specific care for their dog. Will do whatever needed to ensure the safety and well being of our furry friends


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: Over 16 years training, walking and exercising high energy dogs. I have extensive experience with working dogs, special needs dogs and have certifications in dog obedience and other disciplines. I am licensed as a public school teacher and fully background checked. Contact me for the best care. Boarding and adventure daycare is my speciality. I have limited housesitting and drop in availability. Dog walking and exercising is my full-time job. I want to provide a concierge service that makes it easiest for you to take your time back and be well. Your wellness is key to your dog being well. My joy for this profession started when I couldn't find a trusted sitter and dog walker for my own animal. I decided to provide that service to others so they wouldn't have the same problem. I give love, attention and exercise to your family member as if they were my own. I am a licensed public school educator who is fully background checked with glowing references that can be provided and contacted.

About: I've had pets since I was 7 years old and have always loved animals. Currently we have a senior cat and a newly adopted kitten. I enjoy being able to spend time with other people’s pets and ensure they are cared for and have the same routines and schedules as when their pet parents are home. I’ve cared for friends and family's animals in the past. I can administer medicine, follow feeding schedules, walk, play and spend quality time with your pets while you are away. My husband and I moved from Indianapolis to New York in October of 2022. We’ve been spending most our time on home renovations and loving how peaceful our new home is. I am available to stay in client’s home and/or provide drop in care and walks as well. I will follow instructions provided so that you feel confident your pet is well cared for and I will update you with pictures and check in regularly.

About: I live in a two bedroom apartment in Lake George with my dog Stella. I recently lost my other girl Dakota so I would love the extra puppy love. If your pup stays with us, we have a great area for long walks, right by the bike trail down to the lake! We also enjoy hiking if your dog likes that too!! My dogs have usually always slept with me at night but I am not opposed to them sleeping on their own beds. I have a spare bedroom if your pup wants their own space! I will treat your pup just the same as I would want mine treated so they will for sure get tons of love when you aren’t around. I also want your pup feeling as comfortable as possible as well with sticking to the schedule they are used to at home. When booking all visits, I think it is important to schedule a meet and greet so everyone is comfortable. I want your furry friends to get to know me a little bit before the scheduled service. This also gives me a chance to talk to you about your pets likes and dislikes and things that make them happy and things that make them tick! I have experience with dogs and cats of various ages, and temperaments. I hope to get the opportunity to meet you and your furry loved ones soon! I am currently home full time and have a dog of my own! Stella is a top priority and giving her the best life is super important. I like to make sure others animals are treated just as if they were my own. Since I am home the majority of the time, I am able to take frequent walks, spend time relaxing/cuddling and playing. Having my own girl Stella provides an automatic dog pal to have around. If services requested are walking or drop ins, this also opens up my availability for more time to do so.

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.

About: Ive taken care of all types of animals large and small. From monarch caterpillars and goldfish to pigs and horses. I was entrusted with the care of neighbor's pets, friend's farms, and took on the care of the rescued strays as part of the dog control in my hometown. Im no stranger to administering medication as needed. Animals are my livelihood so you can rest assure that your furry, feathered, or scaly family member will be happy, safe, and loved with me :) Last minute changes aren't a problem so if you decide to vacation a little longer, thats no problem. I am flexible with scheduling most days. I am able to come to your house and petsit there making it easier on your fur-family. I can do drop-ins or overnights, daily walks and playtime, feeding, and medication administration. Anything your pet needs, i can provide.

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: 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: I’ve taken care of dogs and cats for 15 years whether it were my own or a friend even a neighbor. My neighbor or for the past two years trusted me with the keys to their home. I have a genuine love for animals. I work around my kids schedules but can be available anytime in advance. My weekly routines are mainly part time but I have flexibility at the moment I can easily crate your dog if needed. I have friendly animals as well. They are familiar with people and another animal. Your pet will be treated like my own

About: Welcome to Marty's pet care service. As a passionate and dedicated pet lover with over 5 years (friends & family) experience, I understand the importance of finding the perfect caretaker for your beloved companions. Whether you are heading out of town or need regular care for your pets, you can trust me to provide them with love, attention, and care they deserve. I am self employed and have a very flexible schedule. I work on projects from home and I am highly accessible via my cell phone. Our home is situated on 7 wooded acres. We have access to wooded trails for leisurely dog walks with our two dogs. All boarders need to be UTD on vaccinations and have flea and tick protection.

About: I am a vet tech assistant, going for my vet tech degree. I have worked in veterinary clinics for over 2 yrs. I have experiences with animals from reptiles, to kittens/puppies, and horses. I plan to pet sit on my days off/up to the first night I have to go into work, which would be Wednesday afternoon around 3pm is the last time I am available for a drop in varying on location could be earlier or a tad later. I love animals very dearly as I have 5 of my own and work in the veterinary medicine industry to help as many as I can. I will make sure your pets are well taken care of. Whether that be a bath, given treats, taken for a walk, let them run in your backyard, car ride, or even just relaxing in the living room. I will treat them as if they were my own.
Loving dog walkers in your neighborhood
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Karen W.
“Karen is the best pet sitter! She will spoil your fur babies! She's great with any kind of pet she's a loving and caring person! She runs her own mini farm with cats, dogs, Guinea pigs, chickens, ducks, turkeys, pigs, rabbits, and fish! Each animal has there own area to run around!”


Jaimi V.

“Went above and beyond!”


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.


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.”


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.”


Brittney R.Star Sitter
“Brittney did an amazing job house-sitting for me. She left my home in fantastic condition, even better than when I left! My animals clearly fell in love with her, and I could tell they were well cared for. I highly recommend her to anyone looking for a responsible and thoughtful house sitter!”


Michelle G.
“Michelle is fantastic! She is reliable and trustworthy and absolutely loves working with dogs. She always puts her heart and soul into her job and is fabulous to have working for you.”




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


Cristina K.
“When it comes to dogs, i couldn't think of a better lady for this occupation! I'm lucky enough to have met Cristina because of our dogs! I helped her to learn dock diving with her boy Hozzy! Hozzy is the most amazing Malinous i've ever met! Sweet, Gentleman and just like my labs! He also obsessed with dock diving! A Champ! Cristina can handle any dog from what i've seen! A 200 lber wouldn't be a problem! She is fun, serious, and full of gusto! She would be a huge asset to anyone needing dog help! She has done many training sessions!! I highlight reccomend Cristina!”


Emily P.
About: I've had pets since I was 7 years old and have always loved animals. Currently we have a senior cat and a newly adopted kitten. I enjoy being able to spend time with other people’s pets and ensure they are cared for and have the same routines and schedules as when their pet parents are home. I’ve cared for friends and family's animals in the past. I can administer medicine, follow feeding schedules, walk, play and spend quality time with your pets while you are away. My husband and I moved from Indianapolis to New York in October of 2022. We’ve been spending most our time on home renovations and loving how peaceful our new home is. I am available to stay in client’s home and/or provide drop in care and walks as well. I will follow instructions provided so that you feel confident your pet is well cared for and I will update you with pictures and check in regularly.


Caitlyn A.
“Caitlyn has helped me out on many occasions watching my dog Lilly who is a pitbull mix. She was always very attentive, loving and caring when it came to spending time with and playing with Lilly. On one occasion Lilly had gotten to one of my medications when it feel on the floor before I could pick it up and Caitlyn was watching her that evening. While I was away, Lilly started acting very unusual and Caitlyn was quick to notice and get her the necessary medical attention. Caitlyn is always very prompt, and thorough with all of her interactions. I would highly recommend Caitlyn for anybody looking for someone to care for their pets!!”


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.”


Alissa V.

“Alissa watched our dog while we got married at country meadows barn. She was great with Romeo and very kind. Thanks!”


Brandy L.
“Brandy has always loved animals and has always been the one to take on the responsibility of the care of them. She has been pet sitting and taking care of animals since she was 11 years old. She has been my go-to person to help with the care of the dogs that come in to my shelter for the last 16 years. I would highly recommend Brandy as she is the only one I would entrust the care of my pets to!”


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!”


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.”


Christian A.
About: I’ve taken care of dogs and cats for 15 years whether it were my own or a friend even a neighbor. My neighbor or for the past two years trusted me with the keys to their home. I have a genuine love for animals. I work around my kids schedules but can be available anytime in advance. My weekly routines are mainly part time but I have flexibility at the moment I can easily crate your dog if needed. I have friendly animals as well. They are familiar with people and another animal. Your pet will be treated like my own


Martn G.
About: Welcome to Marty's pet care service. As a passionate and dedicated pet lover with over 5 years (friends & family) experience, I understand the importance of finding the perfect caretaker for your beloved companions. Whether you are heading out of town or need regular care for your pets, you can trust me to provide them with love, attention, and care they deserve. I am self employed and have a very flexible schedule. I work on projects from home and I am highly accessible via my cell phone. Our home is situated on 7 wooded acres. We have access to wooded trails for leisurely dog walks with our two dogs. All boarders need to be UTD on vaccinations and have flea and tick protection.


Audri G.
About: I am a vet tech assistant, going for my vet tech degree. I have worked in veterinary clinics for over 2 yrs. I have experiences with animals from reptiles, to kittens/puppies, and horses. I plan to pet sit on my days off/up to the first night I have to go into work, which would be Wednesday afternoon around 3pm is the last time I am available for a drop in varying on location could be earlier or a tad later. I love animals very dearly as I have 5 of my own and work in the veterinary medicine industry to help as many as I can. I will make sure your pets are well taken care of. Whether that be a bath, given treats, taken for a walk, let them run in your backyard, car ride, or even just relaxing in the living room. I will treat them as if they were my own.
How Rover works
1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per walk for dog walking in Chestertown is $20
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 dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Chestertown average 4 repeat dog walking clients
Dog Walking FAQs
Frequently asked questions about Rover
Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Chestertown on Rover as of Aug 2025 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Aug 2025, there are 89 dog walkers in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 76% of Chestertown dog walkers respond in under an hour.
Dog walkers with repeat customers have an average of 4 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Chestertown.
You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:
- Start and stop times
- A map of their walk with total distance
- Pee, poo, food, and water breaks
- Cute photos and a personalized note
There are 89 dog walkers in Chestertown on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.
Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog walker 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 dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.
