Dog Walking Chester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Chester, Find top rated dog walking
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Kathleen took such great care of our 8 month old HUGE puppy. She took him for a hike so my husband and I could go skiing at Okemo. She was flexible with timing and was able to drop him at the mtn to meet us after we were done. Highly recommend!!”
“Hillaree is fantastic. She has a firm and caring manner that helped her connect with my dog instantly, and she seems to manage tricky behaviors well. She is very, very reliable and quickly responsive to communications and requests. She provides thoughtful, informative updates about behavior as well as the usual points. I appreciate her so much! She has been caring for my dog weekly for a couple of months and we look forward to many more visits!”
“Milo had such a great experience today! 😊 Paisley was incredibly kind, attentive, and clearly cared about him. She made sure he got everything he needed, followed all of my instructions, and gave me peace of mind knowing he was in such good hands. It’s obvious she genuinely enjoy working with dogs, and Milo came back happy and well cared for. I would absolutely recommend her and will be continuously using her walking services. Thank you for taking such great care of my boy!”
About: Animals kept me safe my entire life, now I return the favor by keeping your babies safe while you’re away. ❤️ I have been working with animals my whole life. At only 3 I moved in with my step father onto a small farm(yes this means I can feed your chickens, gather your eggs, clean your stalls, and feed your cattle, pigs, or even horses). I spent three years working in the veterinary field where I learned to better understand and triage animal emergency and how to deal with them calmly and safely. I have 3 dogs, and 2 cats of my own as well as a bearded dragon and a few chickens, whom I love more than life. I have minimal boarding experience, but have had or worked with everything from fish and birds, to dogs to cattle, from snakes to horses, and I love each one of these creatures just as much as the rest. I adore all animals, and cherish my pets so much, and finding some one you can trust to REALLY care for them can be a challenge, so let me make your life a little easier with flexible, reliable, patient and gentle care. As a pet mom to 11 furry, scaly, and feathered babies, I know how hard it can be to find reliable pet care. My animals are my children, my babies; the most important things in my world. I promise to love yours the way I’d love my own. I am currently unemployed and taking a leap. What I’d LOVE is to start my own pet care company. I know how hard it is to find pet care in and around the Berkshires, especially the holidays when all the day cares and well known sitters are booked - so let me take some of that weight off you. I’m flexible and reliable and can do drops ins, walks, day stays, over nights, or multiple day stays. I’m open to any animal type, including pocket pets, exotics and special needs. What can I say? Pets are really the only thing most of us like in this crazy world; so it’s kind of the perfect job. 😉 I am open to all types of care, all types of animals, and all types of situations. I have experience in vet medicine and have had elderly and special needs animals my whole life. No matter how long my interaction with your baby is, I assure you it will be filled with love.
About: I'm available for all holidays starting with Thanksgiving, Christmas, Hanukkah, Kwanza and New Year's Eve I'm a lifetime pet owner and pet sitter with strong references 🙏 I'm not employed by anyone else, so my time is wide open and I live on a quiet dead end street and close to regular parks and dog parks / trails. I always take the owners preferences seriously, but I do like to spoil with good food and treats. I also am good with grooming calmingly.
About: As a child, I owned almost every pet imaginable - from house cats to Rottweilers to lizards to ferrets! Bless my poor mother's heart - we practically had a small zoo at our house! As an adult I owned a cat for 5 years and also "dog /cat sat" for friends and families many times. I'm an all-around animal lover who is comfortable with many different types of pet care. I'm a stay-at-home mom with a four year old. Please be advised that if I pet-sit overnight at your home, my daughter will most likely be accompanying me for at least part of the job assignment. If you aren’t comfortable having well-behaved, well-supervised children at your home, then unfortunately I’m not a good fit your you. I have plenty of flexibility on both weekdays and weekends to provide care for your pets. I live in a pet-friendly house with a fenced-in back yard. The neighborhood is quiet and safe for walks. I also have access to a nearby park.
About: I’ve been an animal lover for as long as I can remember! I grew up with Labs, so I’m very familiar with big personalities, lots of energy, long walks, playtime, and plenty of slobbery love. 🐾 I also adopted a cat, which taught me that sometimes the best way to win a pet over is to let them come to you (and maybe offer a few treats!). Although my own pets have since passed, they gave me years of experience, amazing memories, and a genuine love for caring for animals. I’m patient, playful, attentive, and always focused on making pets feel safe and comfortable. Whether your pet wants an adventure outside, a game of fetch, or just some extra love and company, I’m happy to be their new buddy while you’re away! ❤️ I currently own my own business and make my own hours and work from home, so I can easily make my own schedule fit around any pet care! I'm lucky to have an open, comfortable and clean home where I can walk animals on the many acres I live on. I can also crate animals if that's how they are trained. When in other people's homes, I'm incredibly conscious of being considerate, following directions to respect their space, and understanding how the animal uses and loves the space.
About: I have always had a pet dog and ever since I was a teenager, I’d dog-sit for family and neighbors. Since college, I’ve been pet-sitting ajd dog walking on a more professional level. I’ve babysat for a few hours, simply for a walk, but have also watched multiple high energy dogs for up to two weeks. I’ve cared for dogs under a year old and up to 13 years old. I’ve always loved dogs and find them very easy to get along with and care for no matter their size, age, or personality. I have also cared for kittens a few weeks old, senior cats, administering medication orally, grooming them if they have long hair etc. Cats have a very different energy than dogs but I enjoy taking care of them just as much as dogs. I am currently in between jobs so I have a lot of free time to care for other dogs, whether it is a short walk or a multi-hour play date, etc. I always follow whatever guidance I am provided by pet parents. This means if you are only comfortable with your dog on a leash or lead while in your yard, I strictly follow that. If there are specific commands to use, certain behavior to watch out for or discourage, particular toys or activities they enjoy, I always follow what information I am given and am always open and communicate well about any issues or concerns that might arise on my end.
“Priscilla is awesome. Our dog is very nervous with people and this is the fastest she has gotten comfortable with someone new. She takes great care of our dog and our dog always comes back happy after walks!”
“Anna did a great job walking our dog. She was friendly and easy to walk with. Zelda had a great time with her - it was our first time using Rover and we had a great experience!”
The median cost per walk for dog walking in Chester is $23
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
How to book dog walking
1. Search
Browse profiles of walkers near you who offer dog walking.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog walking - Chester
Select a filter and find qualifying sitters offering dog walking.Sitters in Chester average 3 repeat dog walking clients
FAQs for Dog Walking - Chester
Frequently asked questions about Rover
As of November 2026, there are 977 sitters on Rover offering Dog Walking across Chester. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in Chester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Chester after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the walk begins.
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.
Every walker 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.
Yes, you can find walkers who have experience with handling special pet needs in Chester. On Rover:
- 91% of walkers can help with special care needs
- 92% can help with giving oral medications or injections
- 96% 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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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 walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
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