Dog Walking Chester

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

End
Search

Over 15
pet parents in Chester have booked dog walking

Chester, Find top rated dog walking

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Joseph G.
Verified Enhanced Background Check
Joseph G.
from
$20
per walk
5.0 out of 5 stars
51 reviews
17 repeat clients
2 years of experience
Chester, NY, 10918

Thank you Joseph! I’ll certainly reach out to you again! I’ll recommend Joseph to walk your dog/s. He is very polite! He was quick in replying to my request, very through following up with a meet and greet and asking questions to make the walks smooth, and finally keeping me updated with times picking up and dropping of my dog. Leo was comfortable with Joseph as soon as they met! My experience was great!

Profile image
Solange M.
Sitter Profile Image: Virginia V.
Verified Enhanced Background Check
Virginia V.
from
$20
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
6 years of experience
Goshen, NY, 10924

Virginia did a great job taking care of our girl!

Profile image
Patti G.
Sitter Profile Image: Mallory K.
Verified Enhanced Background Check
Mallory K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
51 reviews
25 repeat clients
20 years of experience
Goshen, NY, 10924

Thank you for everything Mallory!! She came through for me at very last minute & she is so sweet & easy to deal with. Rusty took to her immediately , he is a big boy & can intimidate some, but she is a true professional! You can tell she genuinely enjoys spending times with dogs. She went above & beyond for me & I can really not thank you enough!!’ I would recommend her to anyone!

Profile image
Latecia B.
Sitter Profile Image: Gavin O.
Verified Enhanced Background Check
Gavin O.
from
$18
per walk
1 repeat client
5 years of experience
Chester, NY, 10918

About: I have personal experience with two dogs (Sunny and Roland) and a cat (Loki). Additionally, I have taken care of the pets of family and friends for years without complaint. I have worked as a dog sitter/walker for over 5 years now, and 3 of those on Rover. Unless my employment status changes, I am available 24/7 over summer, winter, fall, and spring breaks. My time is also very flexible and I don’t mind if I need to work at odd hours. I try to be as gentle and friendly as possible towards pets and will do more than the bare minimum when it comes to exercise and entertainment. I also have experience with cleaning up all kinds of potential messes.

Sitter Profile Image: Giselle G.
Verified Enhanced Background Check
Giselle G.
from
$18
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Goshen, NY, 10924

About: Super flexible schedule! located in Goshen, NY. ** I have experience with reactive dogs, 100+ lb dogs, and a specialty in small animals incl. rabbits, birds, guinea pigs & more ** Whether your pet is in need of a walk, medication or feeding routine, time at home, assistance to their special needs, or checking on their wellbeing, I will ensure your babies get everything they need with a stress-free experience! I would be more than happy to help with pet sitting or dog walking, no matter your pet’s size or age. ♡ I have fully open and flexible availability. I’m able to dog walk and do home drop-ins in Orange County. I can usually squeeze in last minute bookings. If owner would like to opt-in for photos, I’d be more than happy to take some photos of your pet and send them over to you!

Sitter Profile Image: Jake F.
Verified Enhanced Background Check
Jake F.
from
$12
per walk
10 years of experience
New Hampton, NY, 10958

About: I currently cat and dog sit regularly for my parents and for my girlfriends pets when they are away. I have experience dog sitting multiple dogs and love being active with all animals. I am currently on summer break until classes start, once they do schedule may change. Currently I have very open availability, typically get my day started at 9:30am and love being active throughout the day. Pet friendly apartment and neighborhood. I will follow all safety precautions and instructions given. I have a walking path around my apartment. There is a lot of space for pets to roam around.

Sitter Profile Image: Jill S.
Verified Enhanced Background Check
Jill S.
from
$25
per walk
5.0 out of 5 stars
175 reviews
46 repeat clients
57 years of experience
Washingtonville, NY, 10992

You will be in good hands with Jill. My dog loves her and she sends me the cutest pictures of her while I am at work. It always makes my day.

Profile image
Stephanie J.
Sitter Profile Image: Julia R.
Verified Enhanced Background Check
Julia R.
Star Sitter
from
$26
per walk
5.0 out of 5 stars
40 reviews
10 repeat clients
20 years of experience
Warwick, NY, 10990

Julia was terrific! She showed up for a last minute request. She was friendly, prompt and flexible. My dog was very comfortable with her at the outset. I was so impressed that since she needed to address something at home she offered to take my dog with her rather than give me less than the full hour walk.

Profile image
Marcy R.
Sitter Profile Image: Linda B.
Verified Background Check
Linda B.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
31 reviews
14 repeat clients
25 years of experience
Middletown, NY, 10940

Linda was extremely accommodating and took great care of Howie. Would recommend!

Profile image
Kyle B.
Sitter Profile Image: Michael C.
Verified Enhanced Background Check
Michael C.
from
$25
per walk
4.9 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Florida, NY, 10921

Nice Job!!

Profile image
Evelisis V.
Sitter Profile Image: Shannon & Justin M.
Verified Enhanced Background Check
Shannon & Justin M.
from
$30
per walk
5.0 out of 5 stars
8 reviews
7 repeat clients
20 years of experience
Warwick, NY, 10990

⭐️⭐️⭐️⭐️⭐️ Shannon and Justin have been absolutely wonderful with our puppy, Aria! They are reliable, communicative, and clearly care so much about the dogs they look after. We always feel at ease knowing Aria is in such good hands. She gets plenty of attention, playtime, and care during their visits, and they give us great updates each time. It’s such a relief to know we can trust them when we’re at work or away. Highly recommend them to anyone looking for dependable and loving pet sitters!

Profile image
Emily G.
Sitter Profile Image: Erika S.
Verified Enhanced Background Check
Erika S.
from
$25
per walk
5.0 out of 5 stars
41 reviews
13 repeat clients
37 years of experience
Monroe, NY, 10950

Erika was very personable, professional as well punctual. I had knee surgery and was laid up for some time. Erika was there for me she was kind and sweet to Abby gave her a good exercise. She also always asked if I needed something which I found very comforting. I recommend Erika and will surely use her again

Profile image
Joe P.
Sitter Profile Image: Amy D.
Verified Enhanced Background Check
Amy D.
from
$25
per walk
4.8 out of 5 stars
34 reviews
10 repeat clients
20 years of experience
Goshen, NY, 10924

Amy is Fantastic! She is very reliable and always prompt to respond. I had complete confidence in leaving our dog in her care. Highly recommend.

Profile image
Cynthia S.
Sitter Profile Image: Nicole S.
Verified Enhanced Background Check
Nicole S.
Star Sitter
from
$40
per walk
5.0 out of 5 stars
49 reviews
6 repeat clients
15 years of experience
Chester, NY, 10918

About: Although they are no longer with me my boys were my everything and they taught me a lot. I grew up around animals my whole life and love spending time with them especially when they love to snuggle! I currently do pet care full time, I do book up pretty quickly for over night stays but please feel free to to reach out with any questions. Hi, I’m Nicole — your pet’s new best friend! I’m a longtime pet owner and animal lover offering both dog walking and pet sitting services. I care for dogs and cats of all personalities and sizes, including those who are shy, reactive, or just need a little extra patience and understanding. I provide care in your home so your pets can stay comfortable in their own space while you’re away. I’m big on communication — you’ll always get regular updates, photos, and peace of mind knowing your pets are happy and safe. Whether it’s a daily walk or overnight stay, I bring years of experience, calm energy, and genuine love for animals. I can’t wait to meet you and your furry family!

Sitter Profile Image: Samantha K.
Verified Enhanced Background Check
Samantha K.
from
$30
per walk
5.0 out of 5 stars
19 reviews
4 repeat clients
12 years of experience
Campbell hall, NY, 10916

Samantha has been a fabulous walker for us. She is communicative and reliable, and takes excellent care of our dog, we are lucky to have her!

Profile image
Benny H.
Sitter Profile Image: Robbie O.
Verified Enhanced Background Check
Robbie O.
from
$25
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
30 years of experience
Campbell Hall, NY, 10916

About: I grew up on a dairy farm with all sorts of animals around. I have had many dogs, cats, parrots, chickens, rabbits, rats, and horses over the years. I have a degree in Equestrian Science and have taken care of animals my entire adult life. I have always been an avid hiker as well and love to take the pups on walks around the area. I currently own 3 dogs, a parrot, and 2 chickens and will give your animals the same love and attention that I give my own! I'm currently working part time and so have plenty of time to play with your fur babies. I am currently available for house sitting, drop in visits and dog walking. If your dogs get along with mine I might be able to do boarding as well. I have a dog door at my house with a fenced in yard along with 5 acres of fields to walk in. When coming to your home, I use my deep knowlege of dogs, cats, and other animals to keep your animals happy in their own home where your pets are MOST comfortable. They have the comfort of knowing they are safe in a place where they can learn to trust me and we can develop a bond so I can give your pets the same level of love and care as I would give my own pets.

Sitter Profile Image: Maddy A.
Verified Enhanced Background Check
Maddy A.
from
$22
per walk
5.0 out of 5 stars
4 reviews
3 repeat clients
7 years of experience
Warwick, NY, 10990

Maddy was excellent! I booked her as a walker when I was in a pickle last minute, she is very kind and quick to respond. She also makes the extra effort to make sure your fur baby is taken care of, the way I, as an owner would want. Definitely would recommend!

Profile image
Joyce C.
Sitter Profile Image: Jenna C.
Verified Background Check
Jenna C.
from
$30
per walk
4.6 out of 5 stars
18 reviews
3 repeat clients
10 years of experience
Chester, NY, 10918

About: I am a dog lover with 2 dogs of my own, perfect for keeping your dog socialized and playing during their stay. I love to hike with my furry family members and yours will enjoy the same perks! I provide lots of cuddles, lots of excercise, and a perfect scheduled environment to make sure that your dog will feel at home while you’re at work or enjoying a vacation. Feel at peace knowing that your dog is treated just like one of the family here. I also offer dog walking services. During the week, I can provide afternoon/evening walking and drop in services in addition to dog boarding. On the weekends, there is a much wider range of options in my schedule. Since I am a teacher, I have the summers off and can provide many more services over the summer and during my school holidays. I look forward to spoiling your fur-baby! During a work week, I don’t leave home until 7:45, so I have plenty of time to let out both our dogs and yours! I get home quite early in the afternoon since I am a teacher and give tons of love and attention to the pups. We can go for daily evening walks if requested, or just play outside in my yard! During my holiday breaks and the summer, I am home all day and night to give your family member tons of love and attention. My yard is fenced and I have two friendly dogs for your dogs to play with. I’m very familiar with dogs and their behavior, so I know how to approach your dog and make them feel comfortable and happy. Tons of love, attention, and treats offered! Your friend will come home super spoiled and happy, or you’ll arrive back to your home with a happy fur baby to greet you!

Sitter Profile Image: Sade P.
Verified Enhanced Background Check
Sade P.
from
$20
per walk
3.0 out of 5 stars
2 reviews
1 repeat client
6 years of experience
Chester, NY, 10918

About: Hello! I’m a Zoology grad with a soft spot for every kind of pet; from wagging tails to tiny paws and curious scales! 🐕🐁🦎 I completed two years of Animal Science courses in veterinary assistance and continued my training through Penn Foster’s Animal Science program. Along the way, I’ve worked at a large and small veterinary clinic and gained hands-on experience with rodents, reptiles, farm animals, and plenty of dogs and cats. Experience such as how to read behavior, administer medication, spot early signs of illness, and keep every animal conformable and cared for. I’ve also worked at a busy doggy daycare, managing 10+ pups at once (organized chaos at its cutest 😅). Whether your pet needs playtime, patience, or just someone reliable while you’re away — I’ve got them covered. No personality is too big or too shy for me 😄💕 I have open availability and naturally wake up around 6 AM, so early mornings or late nights are no problem. I’ll adjust to you and your pet’s schedule! I treat every pet like my own! Whether at my place or yours, I stick to their normal routine, give them attention, exercise, lots of love and care, plus regular updates so you're mind can be at peace!

Sitter Profile Image: Eryn K.
Verified Background Check
Eryn K.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
186 reviews
56 repeat clients
5 years of experience
Florida, NY, 10921

Eryn is always amazing! I trust her fully with my animals and she is always punctual, kind and lets us know how things go!

Profile image
Jacquelyn E.
1 / 1
View more sitters

The median cost per walk for dog walking in Chester is $25

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.

Meet local walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Chester average 4
repeat dog walking clients

FAQs for Dog Walking - Chester

Frequently asked questions about Rover

The average cost for Dog Walking in Chester on Rover is $26.09 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of July 2026, there are 2,533 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 your Chester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Chester.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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
  • 96% can help with giving oral medications or injections
  • 97% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge