Dog Walkers in Chester, MA

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Chester dog walkers

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Janet M.
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Janet M.
Star Sitter
$23
total per walk
4.9 out of 5 stars
16 reviews
5 repeat clients
53 years of experience
Chesterfield, MA, 01012

Janet is very responsive to msgs, shows up at the scheduled times, and provides summaries of her visit. Thanks Janet!

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Allen B.
Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
$34
total per walk
5.0 out of 5 stars
152 reviews
41 repeat clients
12 years of experience
Becket, MA, 01223

Very positive experience! I was in a bit of a jam, suddenly having to be away from home for 14 hours with nobody to take our dog out. Reached out to Kathleen via Rover, got prompt response, and coordinated the pickup of our dog from our house without ever having met Kathleen. She had my dog out for a romp around a pond with her dog, sent me pictures of the outing, and returned my dog to my house. My problem solved, and it looks as if my dog had a great outing with Kathleen and her dog.

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Ken D.
Sitter Profile Image: Wendy A.
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Wendy A.
$18
total per walk
5.0 out of 5 stars
1 review
1 repeat client
30 years of experience
Westfield, MA, 01085

About: My dad taught me at a young age how to care for, and respect all animals. I have turned this into a life long love for all animals, both domestic and wild. I am a vet assistant, and currently studying to be a certified vet tech. For the last two years I have worked at the local animal shelter, and for the last year, at a dog daycare as well. I have volunteered at Dakin for the best part of the last 15 years. This has included transportation of animals, dog walking, animal socialization, and the kitten ICU. I am currently working part time, so I will have plenty of time for your furry family members. I am available during the week, on weekends, and holidays. Whether your dog likes the dog park, or playing in the backyard, we can play using their favorite toys. If they are more of a couch potato, I can accommodate them as well. If you have kitties that need company, we can play in the house, or go out for a stroller ride. I have a fenced in backyard for the dogs to play in. In the summer, a pool and water sprinkler will be available. I am a vet assistant, so I have first aid training for both dogs and cats. My house is air conditioned, perfect for relaxing on a summer day.

Sitter Profile Image: Hailey P.
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Hailey P.
$20
total per walk
7 years of experience
West Springfield, MA, 01089

About: I’m a graduate student with a bachelors of science in Biology and a concentration in pre-vet, working towards a career in veterinary medicine with years of hands-on experience caring for animals. I’ve worked in a clinical hospital and an animal shelter with both cats and dogs, gaining experience with a wide range of temperaments, ages, and needs. I’ve also taken multiple animal-focused college courses that strengthen my understanding of proper care, behavior, and health. In addition, I’ve provided pet sitting and dog walking for friends, family, and neighbors for several years. I’m comfortable caring for pets of all ages and make sure every animal feels safe, loved, and well cared for. I’m currently working part-time, but I have as much time as I can give for your fur baby! I coach softball so I’m away part of July but other than that my schedule is pretty open. I prioritize pet safety by following routines closely, maintaining clean spaces, and respecting your home. I ensure pets are supervised, secure, and comfortable at all times.

Sitter Profile Image: Fiona B.
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Fiona B.
$34
total per walk
15 years of experience
Huntington, MA, 01050

About: My family owns and operates a Labrador breeding business and kennel, located in a small slice of heaven in the hill towns. I have been living, breathing, and loving dogs for my entire life and find immense joy simply being around them! I have several years of experience at a boarding facility where I was able to expand my knowledge on any different breed, size, age, temperament and disabilities! I am comfortable with all dogs at any life stages, ranging from a few hours old to sweet elderlies. I am also able to react quickly to any situation and have a solid history of preventing and intervening real fights safely between several dogs. I am available at you and your pets desire! I am able to stay in home and/or overnight, or simply check in! My car is my main way of travel, and has safely transported many pups to their playdates! Care in my clients home includes purely love and sticking to the routine that your pet knows the best! My client will also receive the utmost amount of reassurance and open communication because I understand on a personal level how difficult it is to leave your baby in someone else's hands.

Sitter Profile Image: Katelyn G.
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Katelyn G.
$23
total per walk
10 years of experience
Westfield, MA, 01085

About: I’ve taken care of animals for the last 10 years. Dog walking, pet sitting and the occasional sleepover with friends/family animals. I am a newer cat mom (1.5 years) but rest assured, I have picked it up quick! I currently work full time in the school system however I have summers off so I will have lots of time come June to meet new animal friends! I have a half acre lot, not fenced. We currently use an e-collar for our 10 year old golden retriever Charlie. We do have a run available and could easily crate an animal should that be the owners preference. I can also do potty walks as we live in a beautiful neighborhood and close to Stanley Park.

Sitter Profile Image: Saige G.
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Saige G.
$23
total per walk
4.8 out of 5 stars
32 reviews
13 repeat clients
11 years of experience
Easthampton, MA, 01027

Saige aka Ziggy was an absolute dog whisperer. Ziggy took great care of my dog, which allowed me to relax and enjoy my vacation. If you’re looking for a dog sitter or walker, stop searching. One report card wrote “An aggressive dog approached Boone, I stepped in front of Boone and the other dog ran off.” I mean talk about CARE & SAFETY. ⭐️ x 5

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Maris A.
Sitter Profile Image: Caitlin J.
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Caitlin J.
$23
total per walk
5.0 out of 5 stars
4 reviews
20 years of experience
Windsor, MA, 01270

About: I've loved animals forever and have cared for everything from a cockatiel to a chameleon, Great Pyrenees to Pekapoo. I currently have 1 Goldendoodle and 1 chocolate tabby cat in my home with fenced area and walking trails. I'm currently homeschooling my children at our 10+ acre home with fenced area and walking trails. We have a light schedule and are home more often than away. We currently walk our Goldendoodle daily and pet care is our love, in addition to our responsibility. I have a fenced area and multiple indoor secure areas where animals can get healthy time in a safe home without overstimulation. I have 1 Goldendoodle and 1 chocolate tabby cat who are the best of friends and are supportive to newcomers.

Sitter Profile Image: Jonathan M.
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Jonathan M.
$45
total per walk
5.0 out of 5 stars
6 reviews
1 repeat client
12 years of experience
Westfield, MA, 01085

About: I've taken care of dogs since I had my puppy when she was 7 months. I have experience training puppies, taking care of dogs when they are sick, spending quality time with dogs and making sure they are well taken care of. I have experience administering liquid and pill medication to dogs. I am available full-time to watch and walk your pet. Last minute bookings accepted! Will watch your loving animal anytime of day. I am a student on break and my schedule is flexible. I have a home with a fenced in yard. There are no other pets in my home so I will give your animal the love and attention it deserves. I live in a suburban area where I can walk the dog and take long walks. I live nearby a park.

Sitter Profile Image: Melanie D.
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Melanie D.
$28
total per walk
5.0 out of 5 stars
11 reviews
5 repeat clients
14 years of experience
Southwick, MA, 01077

About: I have had a passion for animals since I was little! I love meeting new furry faces and making friends! Snuggles and belly rubs are a must! I bring treats with me to work for all the pups I see on my route! If it’s nice out, I enjoy running around outside or going on hikes. If it gets cooler, I prefer stretching out on the couch. Car rides are always welcome! Visits to the dog park are fun too! Even if they’re safe off leash, I’ll always keep them on leash to prevent any accidents! Muzzled or non-muzzled, I’ll be happy! If you have a list of what they need for food or other supplies, I should be able to follow it no problem!

Sitter Profile Image: Melanie D.
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Melanie D.
$28
total per walk
20 years of experience
Dalton, MA, 01226

About: I grew up with dogs my whole life. My parents also run a dog sitting business on cape cod and I help out there when I can! I am also fully insured! I’m a current second grade teacher, so I’m completely free on the weekends and the summer months, as well as school vacations to take care of your furry friends! I will love your dog like my own! I’m a diligent, reliable and clean person that will leave your home and dog happier than I found it. I am also fully insured!

Sitter Profile Image: Kristin B.
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Kristin B.
$45
total per walk
5.0 out of 5 stars
15 reviews
4 repeat clients
20 years of experience
Goshen, MA, 01032

About: Have owned dogs for over 20 years, pet sit for friends, family, and neighbors. I am over cautious and protective when it comes to animals, I'm also active so love walking dogs, throwing a ball for them, or taking them to our local lake for a swim. I have tons of patience for shy dogs, I have dealt with rescue dogs and know when to get close or not to an animal. I have never had an incident where I have had a dog become aggressive with me. I have taken my own dog to obedience school a few times and learned a few key trips for working with difficult dogs or puppies. I have taken care of puppies within the past three years and am comfortable with the extra care they require. I have a solid connection with our local vet and emergency animal hospital and am able to handle dogs who need shots or medications administered. I work from home and have several pets already needing care. Bathroom breaks, walks, ball throwing, catnip time, all of it already happens in my home. We have several pet fences within our home and a puppy proof first floor. If a pet is okay of leash then we walk them around our 4 acres throwing a ball or whatever the pet likes. If a pet is not okay off leash, then we just walk them on a leash on our land every 1.5 or 2 hours or as needed. Water bowls are everywhere, no chemicals are on site within reach of curious puppies, and no cars move very quickly on our driveway and everyone who does arrive at our home knows we have several pets and need to slow down. We have owned dogs for over 25 years and have never had any of our pets get injured.

Sitter Profile Image: Charlotte W.
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Charlotte W.
$18
total per walk
1 year of experience
East Cambridge, Amherst, MA, 01003

About: I’ve grown up caring for and loving animals my entire life! Taking care of animals comes naturally to me, I love walking dogs, feeding them, playing with them, and believe it or not cleaning up after them! While I don’t have any professional experience yet, my personal experience makes me qualified to deal with any challenges as I’ve been trusted in the past! Pet care fits into my daily life with me having to take care of my pets! I have two dogs, one is a german shepherd, the other is a Chiweenie. I love taking care of them and taking them for nice long walks! I care for my pets as well as my clients pets as I show them respect and I show them how much I care about their needs. I care for my own pets by feeding them, cleaning up after them, walking them, and if needed washing them. I would show these same principles to my clients dogs and animals as well

Sitter Profile Image: Jonathan A.
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Jonathan A.
$17
total per walk
5.0 out of 5 stars
14 reviews
4 repeat clients
30 years of experience
Northampton, MA, 01062

Jonathan was wonderful with my dog. He was happy help me out in a pinch, and while I never got to meet him, my roommates raved about how good he was with my high energy mutt. He was able to keep up with her and outsmart her when play time was done. Definitely would recommend!

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Rhyan F.
Sitter Profile Image: Amad E.
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Amad E.
$28
total per walk
5.0 out of 5 stars
32 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

About: I've been house and pet sitting for ten years plus, besides that I've been an owner of many dogs and cats. There is nothing that makes me happier than the well-being of them. When you choose me for the care of your fur babies, they'll be taken care of to the maximum comfort and standard. I'm flexible in that I work remotely... So i huge amount of the time i will be around to cater to your pets. And also will be able to walk them often and keep them stimulated I'll make sure their safety and the environment they're in are safe and nurturing. If it's the owner's house I won't change a thing, if it's my house I'll have them have access to all that they would have at their home.

Sitter Profile Image: Reymon B.
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Reymon B.
$23
total per walk
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

Sitter Profile Image: Laila S.
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Laila S.
$28
total per walk
5.0 out of 5 stars
34 reviews
1 repeat client
3 years of experience
Southampton, MA, 01073

About: I have trained my dog since she was a puppy and love spending time outside with her. I love to stay active with the pups but also enjoy relaxing and providing pets. I’m currently a full time student at Umass Amherst but I am home in Southampton in the summer and would love to help out! Whether that’s a quick walk or a longer stay I will always offer the upmost respect in a clients home. I make sure to provide my undivided attention to all pets and leave the clients home untouched.

Sitter Profile Image: Michael B.
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Michael B.
$18
total per walk
24 years of experience
Deerfield, MA, 01342

About: I’ve had pets since I was about 4 years old, and am experienced with caring for cats and dogs. Any needs they have, I will take care of them all - from simple company when you're at work, to walks, giving meds and overnight stays! I have experience training puppies too, from potty training to the classic "stay", "sit", "come", "leave" etc. commands. I have a large dog myself so size of your pet is no issue. Anything you're unsure about, shoot me a message! I work full time at a school but am free weekdays after 2pm until around 10pm. On weekends I am free from Friday afternoon until Monday morning so I can do overnight stays too if needed. Depending on the care required, I will feed pets, give them meds, take them outside, play games/fetch/etc., brush them, empty litter boxes and so on. I have had several cats and dogs of my own and cared for many more, so I am comfortable with adjusting to their different personality types.

Sitter Profile Image: Steve F.
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Steve F.
$56
total per walk
5.0 out of 5 stars
1 review
2 repeat clients
12 years of experience
Lee, MA, 01108

About: I'm very happy to be around pets. Have experience taking care of pets as I have had pets growing up I have been called to dog wisper because I have that connection with dogs. Your pet will be well cared for and loved in my care I'm open mornings and at night.i do food delivery and housekeeping part time.i can usually be available for whatever times you need just reach out and let me know I have a eye for detail and.very alert so your pet will be safe. What ever kind of pet sitting you need I can do

Sitter Profile Image: Evan A.
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Evan A.
$34
total per walk
5.0 out of 5 stars
5 reviews
10 years of experience
Florence, MA, 01062

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.

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The median cost per walk for dog walking in Chester is $22

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Sitters in Chester average 4
repeat dog walking clients

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Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Chester on Rover as of Jun 2026 was about $22 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.

If you’re searching for a Chester dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 478 dog walkers in Chester. 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, 83% of Chester dog walkers respond in under an hour.

Dog walkers in Chester have an average of 17 years of experience. 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 Chester.

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 478 dog walkers in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 95% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked 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.