Dog Walkers in Chester, NY

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. 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.
Star Sitter
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: Mallory K.
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Mallory K.
from
$22
per walk
5.0 out of 5 stars
45 reviews
23 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: Julia R.
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Julia R.
Star Sitter
from
$26
per walk
5.0 out of 5 stars
37 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.

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Marcy R.
Sitter Profile Image: Julia D.
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Julia D.
from
$20
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
9 years of experience
Chester, NY, 10918

About: I currently work full time from home with a friendly pup of my own. I graduated from the Orange-Ulster Boces animal science program in 2018 where I received my Vet Assistant certification, along with my Pet-Aid CPR certification, and have been pet sitting on and off since 2016. My job offers a lot of flexibility for long walks mid day and my dog is also 30-lbs of love and energy, always excited for new friends. Whether you need me there with your pet or if you’d prefer to drop them off to me we can discuss further to see what will work best. Since I do have a dog of my own, id be open to having 1 other small or medium dog here with her and I, otherwise, we can discuss drop ins at your home instead. I want nothing but the best for you and your best friend, so if have any questions, feel free to ask! I currently work full time from home Monday-Friday. This allows me to take breaks where needed, taking my dog for long walks and including another pup in our day to day. Since I don’t work weekends and am off most holidays, that also allows more flexibility on my end to care for your pet whether here or in your home. In my home, I have a 30 lb pup who loves to play and would be happy entertaining more throughout the day and would be very happy to have a new walking buddy for our longer daily walks. I also have many bones and treats and different stimulation activities to keep my dog entertained even on rainy days. I have a nice balcony that she loves to sit on and get some fresh air and people watch which has a seat for her and any other doggy friend! My dog is very spoiled with toys as well and a medium sized crate if needed. We also live a step away from a long walking trail or a quick ride to a few different dog parks if the weather allows. Your pet, whether in my home or yours will be treated just as my own!

Sitter Profile Image: Amber C.
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Amber C.
from
$35
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: Shannon & Justin M.
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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!

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

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

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Kyle B.
Sitter Profile Image: Michael C.
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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!!

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Evelisis V.
Sitter Profile Image: Erika S.
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Erika S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
41 reviews
12 repeat clients
37 years of experience
Monroe, NY, 10950

My first time trying Rover and it was a great experience. Erika took great care of my pups while I was away. I highly recommend her and I will use her again.

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Theresa U.
Sitter Profile Image: Jenna C.
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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: Jill S.
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Jill S.
from
$25
per walk
5.0 out of 5 stars
170 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.

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Stephanie J.
Sitter Profile Image: Robbie O.
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Robbie O.
from
$25
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
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: Marlenie M.
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Marlenie M.
from
$15
per walk
5.0 out of 5 stars
2 reviews
2 years of experience
Middletown, NY, 10940

Marlenie was so kind to take Trudy on a walk for me. I’ve been sick and haven’t been able to walk her and I felt so bad, but Marlenie saved the day! She was available within an hour of when I contacted her. This was my first experience using a dog walker and it was definitely a good one! Thank you!

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Kiara S.
Sitter Profile Image: Sade P.
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Sade P.
from
$20
per walk
5.0 out of 5 stars
1 review
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: Samantha K.
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Samantha K.
from
$30
per walk
5.0 out of 5 stars
17 reviews
3 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!

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Benny H.
Sitter Profile Image: Raquel P.
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Raquel P.
from
$25
per walk
5.0 out of 5 stars
32 reviews
12 repeat clients
6 years of experience
New Hampton, NY, 10958

Cannot recommend raquel enough! She did a great job of providing quality updates, and ensuring my pup had plenty of love while I was away. Will definitely be using her more in the future!

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Mandy R.
Sitter Profile Image: Rebecca M.
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Rebecca M.
from
$25
per walk
5.0 out of 5 stars
25 reviews
4 repeat clients
40 years of experience
Goshen, NY, 10924

About: 🐾 TOP 10 REASONS OUR DAYCARE IS A PAW ABOVE THE REST 🐾 1. See Your Pup Anytime We offer a live webcam option so you can check in during the day, plus videos and photos sent to you consistently every 1–2.5 hours. You’ll always know your fur baby is safe, happy, and loved. 2. Love Like They’re My Own I’m a proud fur-mom myself — my dog is my heart. Under my care, your pup becomes part of my family, receiving the same love, attention, and TLC they deserve. 3. Professional, Medical Expertise I’m a licensed, registered nurse trained in pet CPR, medication administration, and caring for toy breeds and seniors. Health, safety, and well-being come first. 4. Engaging Walks & Mental Stimulation Daycare includes 2–3 interactive outdoor walks plus potty breaks as needed. Overnight stays include 4 walks. We explore nature, encourage play, and keep minds sharp with puzzles and paw-friendly games indoors. 5. Individualized 1:1 Attention Every pup gets personal playtime, cuddles, and socialization. 6. Fur-Family Celebrations We celebrate birthdays and milestones with pup-friendly parties! 7. Home Full-Time Your pup is never left alone for more than 20 minutes. Full-time care means full-time love. 8. Fun Field Trips Outings to dog-friendly cafés and parks keep things exciting. 9. Spotless, Safe, Sunny Home A clean, bright, pup-friendly environment that’s sanitized daily. 10. Exclusive Discounts First-time clients, extended stays, and referrals all get special pricing. ⸻ 💡 Bonus Care Perks • Daycare Rate: $75 for 8 hours, includes two 30-minute walks + potty breaks. Additional hours: $10/hour. • Overnight Rate: $150 for 24 hours, includes four walks. • Complimentary Mini Groom: Your pup comes home clean, fresh, and styled. • Optional Webcam or frequent photo/video updates. • Training Support: I have dog training experience (not certified). ⸻ 🏡 Why Choose Me Over Larger Facilities? When you book with me, you’re guaranteed that your pup will be with me 100% of the time — not left alone while the caretaker runs other walks or drop-ins. Safety, supervision, and affection are constant. Group play is encouraged, but every dog gets individualized love and attention. ⸻ 📅 Book Your Meet & Greet A quick chat or in-person meeting helps me learn your pup’s needs and ensures a happy, stress-free stay. 📲 Contact Me 20% off first-time clients! Rover Code: REBECM30584 Book on Rover Here I work part time from home in the *evenings* so my complete undivided full attention is on your furbabies ensuring their enjoyment, exercise and mental stimulation. Even when walking with them, I continuously interact by talking and encouraging them. This is not your typical mass daycare where the majority sign up as many babies as possible to generate the most income, all the while most are ignored or left to their own vices to provide themselves with their own socialization and care. This is a boutique individualized daycare which means only 4-5 at the very omost daily as the ultimate goal is to enrich and foster love in the daily life of your baby. To provide safety, 1:1 care and genuine enriched intellectual fun and stimulation only a very small group are accepted. I am covid vaccinated and up to date booster along with the flu vaccine. My apartment is kept clean, sanitized, safe, child proof and doggie proof! And no, I have no “human children” but I do have a fur baby of my own and safety is my number one priority

Sitter Profile Image: Nicole S.
Verified Enhanced Background Check
Nicole S.
Star Sitter
from
$40
per walk
5.0 out of 5 stars
46 reviews
5 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: Amy D.
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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.

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Cynthia S.
Sitter Profile Image: Vicky A.
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Vicky A.
from
$25
per walk
5.0 out of 5 stars
7 reviews
2 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.

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Over 28
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The median cost per walk for dog walking in Chester is $25

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Sitters in Chester average 3
repeat dog walking clients

Dog Walking FAQs

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 Mar 2026 was about $25 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 Mar 2026, there are 1,364 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, 89% of Chester dog walkers respond in under an hour.

Dog walkers in Chester have an average of 16 years of experience. Dog walkers with repeat customers have an average of 3 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 1,364 dog walkers in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 91% 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.