Dog Walking Chester

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Over 14
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.

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Sitter Profile Image: Joseph G.
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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!”

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Solange M.
Sitter Profile Image: Giselle G.
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Giselle G.
from
$18
per walk
5.0 out of 5 stars
• 6 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: Mallory K.
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Mallory K.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 52 reviews
26 repeat clients
20 years of experience
Goshen, NY, 10924

“Mallory is a wonderful person and great communicator for scheduling. Always on time and my dog loves her. I enlisted her services because of my bad back, and she has been a miracle while I try to fix my back issues. 1000/10 would book again!”

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LunaM13
Sitter Profile Image: Lauren L.
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Lauren L.
from
$20
per walk
10 years of experience
Chester, NY, 10918

About: Pets are family, so when I’m taking care of your child/home, I’ll keep it tidy, keep you updated, and keep in touch! I’m currently attending school full time, so I will be most available early mornings and later nights during the week. I am available all weekend Friday-Sunday. I have a big yard with a lot of land to work with. I have 2 friendly dogs of my own. I can leave a crate safely in my home as well.

Sitter Profile Image: Erika S.
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Erika S.
from
$25
per walk
5.0 out of 5 stars
• 42 reviews
14 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”

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Joe P.
Sitter Profile Image: Jill S.
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Jill S.
from
$25
per walk
5.0 out of 5 stars
• 181 reviews
48 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.”

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Stephanie J.
Sitter Profile Image: Julia M.
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Julia M.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 11 reviews
5 repeat clients
20 years of experience
Washingtonville, NY, 10992

About: I have many years of experience living with and caring for a variety of animals of all ages. I've had cats in my own home my entire life and have owned dogs as well for the last 10 years. Neighbors and friends have trusted me with caring for their pets since I was 12 years old. I've also cared for horses and competed in the equestrian sport for over 20 years, which requires a high level of responsibility and discipline. All of this experience has allowed me to develop a great understanding of animal behavior, communication, and basic training concepts. You can trust me to safely care for your furry loved ones as if they were my own with lots of love, cuddles, and play! Im available with a schedule that is flexible during the week and on weekends - please check with me for my current availability for bookings! I can adapt to the needs of your pet whether it is caring for an indoor cat who needs food, water, litter, and attention, or a dog who needs to be walked around the neighborhood or exercised with a game of fetch in a safe fenced in area. I will always allow the animal to lead in establishing a trusting relationship with me. I have enough experience to identify signs of distress in an emergency and can also apply basic training methods in a warranted situation while walking a dog on a leash in order to keep everyone safe.

Sitter Profile Image: Linda B.
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Linda B.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 45 reviews
17 repeat clients
25 years of experience
Middletown, NY, 10940

“We felt very confident with Linda taking care of our dog. She came over prior to when we needed her to meet our go & get to know her. She was easy to reach when we had questions. A great 1st time Rover experience.”

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Ken R.
Sitter Profile Image: Robbie O.
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Robbie O.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 8 reviews
3 repeat clients
30 years of experience
Campbell Hall, NY, 10916

“Super reliable and i can always trust her with my dogs”

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2fit2quit_ b.
Sitter Profile Image: Brittany C.
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Brittany C.
from
$20
per walk
5.0 out of 5 stars
• 1 review
23 years of experience
Goshen, NY, 10924

About: I will treat your pets like family. I have one cat and one small Pomeranian. If your pet has special needs I am able to dispense medication. I love giving animals attention and love. I have a large house and a decent sized backyard. I am able to travel to your pets. I have pet first aid experience. I am alert and watching your pet at all times. I have had pets since I was born. I grew up around both cats and dogs. I have a non-profit where I super coupon for pet food and pet supplies and donate them to my local animal shelter. 50% of the money I make on here goes towards funding my donations for the animal shelter. Thank you for your time.

Sitter Profile Image: Julia R.
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Julia R.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 43 reviews
10 repeat clients
30 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.”

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Marcy R.
Sitter Profile Image: Amy D.
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Amy D.
from
$25
per walk
4.8 out of 5 stars
• 39 reviews
11 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.”

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Cynthia S.
Sitter Profile Image: Amber C.
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Amber C.
from
$37
per walk
5.0 out of 5 stars
• 12 reviews
2 repeat clients
25 years of experience
Chester, NY, 10918

About: As a lifelong animal lover, I have multiple years experience caring for dogs, cats, pocketpets, rabbits, fish, parakeets, reptiles and chickens. I also have experience providing care in a rabbit/cat/small animal rescue and in stables so I am very well rounded when it comes to all manner of pet care. I am comfortable walking, feeding, playing, etc. Currently my schedule is generally Monday-Friday 8:00am-5:00pm with a bit of leeway here and there. I can do walks and drop ins on evenings and weekends. Knowing what your pet needs in advance makes it easier for me to set my upcoming schedule to accommodate them. And as an added bonus when it comes to working from home: House sitting is a breeze! I am able to give tons of attention during the work day and use my breaks to take pups out for walks and play time. For my own pets I have two cats and guinea pigs. The guinea pigs have a large cage in my spare room/office and there is plenty of room to board other pocket pets if need be. For other people's pets I will absolutely treat them with the same care and attention as my own. I understand that each pet and family is different so I will use your guidance and details to know exactly what your pet needs to make them happy and comfortable!

Sitter Profile Image: Maddy A.
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Maddy A.
from
$22
per walk
4.9 out of 5 stars
• 9 reviews
5 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!”

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Joyce C.
Sitter Profile Image: Alexa S.
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Alexa S.
from
$30
per walk
5.0 out of 5 stars
• 5 reviews
2 repeat clients
10 years of experience
New Hampton, NY, 10958

“Alexa is beyond great! She is a pitbull aficionado and I’m sure she knows a lot about other dogs as well. I feel blessed to have found her! My dog absolutely loves her! She knows so much about dogs that I’m learning from her. Thank you so much Rover for getting us together. I am beyond grateful.”

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Linda C.
Sitter Profile Image: Natisha D.
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Natisha D.
from
$30
per walk
4.8 out of 5 stars
• 77 reviews
36 repeat clients
2 years of experience
Goshen, NY, 10924

“Words will never be enough to express how unbelievably thankful I am to Natisha!! She accepted a contract on VERY SHORT NOTICE!!! She agreed to be there for me and my family with less than 24 hours notice for twice a day walks for my 2 kids (2 dogs). She came same day to meet with us and was sweet, understanding and flexible. It was our first time. It was hard to trust and we were so nervous!! She made it easy with daily check-ins, texts and pictures! We highly recommend and will DEF use her again! THANK YOU NATISHA!!!”

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John J.
Sitter Profile Image: Shannon & Justin M.
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Shannon & Justin M.
from
$30
per walk
5.0 out of 5 stars
• 11 reviews
8 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!”

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Emily G.
Sitter Profile Image: Michael C.
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Michael C.
from
$25
per walk
4.9 out of 5 stars
• 9 reviews
1 repeat client
10 years of experience
Florida, NY, 10921

“Nice Job!!”

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Evelisis V.
Sitter Profile Image: Vicky A.
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Vicky A.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 20 reviews
8 repeat clients
15 years of experience
Middletown, NY, 10940

About: I love dogs and would love to host your furry friend during your getaway. It's no trouble to give medication as needed (I can give pills without treats and I can give meds by dropper) and your pup would get at least 1/2 hour walking per day if they are up to it, on trails if you're ok with that. Please let me know beforehand if there are any exercise restrictions. I'll be happy to send pictures of your pup during their stay. I will house sit medium sized dogs and smaller. For boarding, my apartment is small and is better for dogs on the smaller side. I would board a dog 40lb or smaller, who is current on their shots and not sick at the time. Please feel free to ask if you have any special requirements for your dog that I haven't mentioned. I have plenty of time to play with pups and I can walk dogs during the day. If they stay with me, they will hang out while I work from home, and go on at least 2 walks for 20-30 minutes. I do daily pupdates, sending pictures so you can see what your furry baby is up to. If I house sit for you, I can watch a 2 medium/small sized dogs and/or cats. I will be mindful in your home and be a good guest. I can give pills or dropper medication to dogs if needed. If you board with me, pets are welcome on the furniture (because snuggles matter!). I live in a small apartment, best suited for chill or medium-energy pups—not zoomies. I am keeping the happiness and well-being of your pet in mind - we will play and walk 2-3 times per day.

Sitter Profile Image: Carole S.
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Carole S.
from
$20
per walk
1 year of experience
Washingtonville, NY, 10992

About: Hi! I’m a devoted dog mom to Millie, my Cavalier King Charles Spaniel, and I bring that same hands-on care to every dog I look after. Raising Millie has taught me how much dogs thrive on consistency — reliable potty breaks, patient leash time, and reading their cues. I’m comfortable with feeding schedules and specific dietary needs, and I love a good sniff-led walk that lets a dog explore at their own pace. I’m patient, observant, and treat every dog’s home and routine like my own. Expect close attention to your instructions, thoughtful updates, and a sitter who genuinely loves the work. Looking forward to meeting your dog! 🐾 Pet care is already woven into my everyday routine — I’m home with Millie for feedings, potty breaks, and walks multiple times a day, so caring for a dog on a consistent schedule is second nature to me. I’m happy to build drop-in visits around your dog’s existing routine, whether that means a quick midday potty break or a longer afternoon walk. Since I’m mainly offering drop-in visits and walks, I focus on keeping things consistent with what your dog already knows — following their regular schedule, feeding routine, and any specific instructions closely. In my own home, I’m hands-on with Millie’s daily care, from meals to sniff-led walks, and I bring that same patience and attention to detail into your home so your dog feels comfortable and looked after.

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

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Popular requests for dog walking - Chester

Select a filter and find qualifying sitters offering dog walking.

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 $27.75 per walk (as of September 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 September 2026, there are 2,485 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:

  • 92% 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.

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