Dog Walking Chester

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

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Over 14
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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: Monta K.
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Monta K.
from
$23
per walk
10 years of experience
Chester, NY, 10918

About: Hi there, fellow pet lover! :) I grew up with dogs, cats, a rabbit, chickens... and yes, even a cow and goats! I'm new to Rover, but caring for animals has always come naturally to me. I work for myself, so my hours are flexible and your pet gets real attention, never a rushed visit. I'm happy to send photo updates and even water your plants! I work from home and have a car so I'm pretty flexible! Mornings and midday are when I'm at my best, and early evenings work too, just no late nights please :) For now, I'm not able to host pets in my own home, but I'm happy to come to yours! you can trust me to follow your instructions, keep doors and gates secure, and treat your home with care and respect. I'll keep you updated with photos so you alway know how things are going.

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: Jill S.
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Jill S.
from
$25
per walk
5.0 out of 5 stars
• 182 reviews
48 repeat clients
57 years of experience
Washingtonville, NY, 10992

“Jill was fantastic! I reached out at the last minute right before Thanksgiving when other accommodations feel through. She was so great when she met our poodle, who immediately was comfortable. Jill was very communicative on the walk day, and sent some great pics of their walk around the neighborhood. Can’t wait to book with Jill again. Thank you!!!”

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Nancy V.
Sitter Profile Image: Nancy C.
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Nancy C.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
• 9 reviews
5 repeat clients
10 years of experience
New Windsor, NY, 12553

“Great with my huskies!”

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Jaleesa L.
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: Julia R.
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Julia R.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 43 reviews
11 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: 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: Jacklyn S.
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Jacklyn S.
from
$30
per walk
5.0 out of 5 stars
• 5 reviews
1 repeat client
23 years of experience
New Hampton, NY, 10958

About: I have been taking care of pets for almost 30 years. I have also worked at a veterinary hospital for about 5 years as a vet tech. I love every pet like they are my own I am a stay at home mom so I am available anytime of the day. Some days I will have to bring my son with me. Early mornings and evenings. I am one call away to care for your pet. I care for your pet just like they are my own. I make sure they have everything they need and time to exercise and get their energy out. If they need medication I am there for them. Whatever they need

Sitter Profile Image: Jade Marie C.
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Jade Marie C.
from
$20
per walk
5.0 out of 5 stars
• 15 reviews
3 repeat clients
4 years of experience
Middletown, NY, 10940

“Friendly and great with dogs. Even my grumpy dog liked her.”

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Phab C.
Sitter Profile Image: Hannah W.
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Hannah W.
from
$15
per walk
5 years of experience
Warwick, NY, 10990

About: I’ve grown up with pets, both dogs and cats, my entire life. I house sit for family members with pets and take it upon myself to love and care for them like they are my own. I love to take them on adventures in the car, to walking trails or lakes to engage with them! I currently work a full time job Monday through Friday in office with one day to work from home. I can provide evening and night care, as well as weekends! I can be flexible as well to stop in at nights or early mornings for your pet needs. I am willing and able to house sit and adjust myself for your pet’s schedule and comfort. I have one dog and one cat in my home who are cared for around the clock. I love taking my dog for visits to different state parks or hiking trails!

Sitter Profile Image: Shelby T.
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Shelby T.
from
$18
per walk
1 year of experience
Westtown, NY, 10998

About: I’ve been certified as a Vet Assistant, I am also currently in school for my license as a Vet Technician. I’m very confident that I will be a safe environment for your furry friends! I’m currently a student so weekends will be more manageable for me, In case of any emergencies of course I can make accommodations during weekdays. I’ve had more than 11 animals my whole life growing up (5 dogs) (4 cats) (2 two fish) I would say I’m extremely experienced in caring for animals. Professionally my experience would be under a year as I am still in school, I live on 67 acres and a large yard which will give your dog enough room to run with the wind and enjoy the fresh air.

Sitter Profile Image: Danian C.
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Danian C.
from
$18
per walk
2 years of experience
Harriman, NY, 10926

About: i have walked dogs and cared for them for as long as i can remember, im pretty good at reading body language and predicting behavior in order to understand the needs and desires of the dog/cat in my care. i basically have open availability, im either looking for a dog/cat to care for or working for doordash. i have my 100% attention on being there for your pets. i care for your pets by staying in toutch with the parent owner and giving little updates and moments, or any questions i have to fully understand and respect the boundaries of not only the pets but the parents and how things should be done and all the tasks required of me.

Sitter Profile Image: Beata L.
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Beata L.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 3 reviews
2 repeat clients
16 years of experience
Tuxedo Park, NY, 10987

“Beata was so great! She was such a sweetheart and oki had such a great time with her. Will definitely book her again.”

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Saeun Y.
Sitter Profile Image: Leah O.
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Leah O.
from
$40
per walk
8 years of experience
Monroe, NY, 10950

About: Hi, I’m Leah! Animals have always been my passion, and I take pride in providing safe, loving, and reliable care. As a dog mom, I understand how important it is to find someone you trust with your pet. I have experience caring for dogs, cats, and horses, and I treat every pet like family. I offer personalized care based on your pet’s unique needs and provide flexible scheduling, including evenings and weekends. I look forward to caring for your furry family members! Pet care fits naturally into my daily routine. I have a flexible schedule that allows me to provide dependable care, including walks, feeding, playtime, and companionship. I enjoy staying active and making sure each pet receives the attention, love, and consistency they deserve. I care for every pet as if they were my own by following their regular routine to help them feel comfortable and secure. Whether in my home or yours, I provide plenty of attention, exercise, playtime, fresh food and water, and lots of affection. I also follow any special instructions, including medications, feeding schedules, or other specific care needs, to ensure your pet stays happy, healthy, and well cared for while you’re away.

Sitter Profile Image: Diana H.
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Diana H.
from
$65
per walk
5.0 out of 5 stars
• 8 reviews
1 repeat client
18 years of experience
Middletown, NY, 10940

About: I’ve been a pet owner all of my life as well as caring for pets.I truly love animals and so do my kiddos! I’m a stay at home mom so I have all the time for you fur baby ! May fiancé works in law enforcement in NYC ( detective) your pup is safe with me ! I also have nanny cameras since I have toddlers ! Spoiler alert ! Your pup will be spoiled while in my care 🥰 I’m a stay at home mom so pet sitting works out well for my schedule and routine. Overall, the pets will be taken care of with the up most care and love! I love the interaction with all dogs and their cute personalities. I like to hear what the client would like in regards to care and how their normal routine goes in their homes. I like to help the client keep their pet on the schedule they’d normally have at home. Dogs will be walked on a leash at all times. I also use puppies wipes to clean up their paws/other areas after walking outside🙂.

Sitter Profile Image: Lizbeth S.
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Lizbeth S.
from
$30
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
15 years of experience
Westtown, NY, 10998

About: Hello! My name is Lizbeth. Pets have been a part of my life since I was young. And throughout those years my family and I have had and cared for several dogs and my own cat. I have experience from caring for puppies to senior dogs with disabilities. I love to spend time with them and look forward to meeting your pet family. Please don’t hesitate to reach out with the schedule you are seeking care for, I am flexible and will be more than happy to work with your schedule if that is something I can do. I currently have a part time job and l am available most mornings and early afternoons. My schedule varies week by week and is flexible, so please feel free to reach out! I am more than happy to adapt to what each client needs/prefers and what each pet is used to. My main goal is to help each family and pet that I work for to feel happy and comfortable.

Sitter Profile Image: Victoria F.
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Victoria F.
from
$25
per walk
5.0 out of 5 stars
• 5 reviews
1 repeat client
5 years of experience
Bloomingburg, NY, 12721

About: I’ve worked with dogs of all shapes and sizes, I have volunteered countless hours in a shelter and have lived with dogs for the last 10 years. I have experience with both pure breed and rescues. I am an active person so your dog will always have someone to play with! I currently work nights so late night or early morning visits are never an issue! I love to stay active and four legged friends the attention they deserve, so if you want your animal to not only be acted for but loved then please reach out to me. Depending on the services provided and your dogs actively level I would love to take them for a long walk or chase each other in the backyard. I am currently a nursing student so I enjoy having an outlet of pet therapy to distract from the stress of school work.

Sitter Profile Image: Eric S.
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Eric S.
from
$22
per walk
4.8 out of 5 stars
• 52 reviews
16 repeat clients
15 years of experience
Montvale, NJ, 07645

“Was very communicative and friendly! Took them on a great walk and kept me informed about how it went! Would totally reach out again for future walks!”

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Jordyn L.
Sitter Profile Image: Jennifer N.
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Jennifer N.
from
$17
per walk
15 years of experience
Newburgh, NY, 12550

About: • Specialized Senior Pet Care – Gentle handling, mobility support, medication administration, and extra patience for slower-paced walks or special routines. • Health & Comfort Focused – Attentive to changes in mood, appetite, or mobility, with prompt updates if something seems off. • Customized Care – From joint-friendly play to warming up meals, I tailor every visit to your pet’s needs. • Reliable & Communicative – Daily updates with photos and videos so you feel connected and reassured. • Compassionate & Calm – I take my time, ensuring your pet feels safe, loved, and never rushed. Pet care is a priority in my daily routine. I’m available for morning, midday, and evening visits, as well as overnight stays when needed. My flexible schedule allows me to adjust to your pet’s feeding, walking, and medication times. Consistency is key, so I make sure my visits are always on time and unrushed—your pet gets my full attention every time. When caring for pets in a client’s home, I treat their space and their animals with the same respect and care as I would my own. I follow the pet’s regular routines—feeding, walking, playtime, and any special instructions—to keep them comfortable and stress-free. I make sure fresh water is always available, litter boxes are cleaned, and living areas are tidy. If medications are needed, I administer them exactly as directed. I also spend quality time giving affection and companionship, so your pet feels secure while you’re away. Before leaving, I ensure the home is secure, lights and doors are as you prefer, and you receive an update with photos so you know everything is safe and well.

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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.

How to book dog walking

  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.

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 of Dog Walking in Chester is $28 per walk as of October 2026. Most bookings cost between $0 and $33 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 2,465 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 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 , 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 , 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 .

Yes, you can find walkers who have experience with handling special pet needs in Chester. On Rover:

  • 87% of walkers can help with special care needs
  • 91% 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 .

walkers on Rover set their own , 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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