Dog Walking Chester

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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: Laura G.
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Laura G.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
112 reviews
33 repeat clients
16 years of experience
East Haddam, CT, 06423

Great job! Thanks again!

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Chelsea G.
Sitter Profile Image: Kristen M.
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Kristen M.
from
$25
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
45 years of experience
Killingworth, CT, 06419

About: I’ve had dogs my whole life and absolutely love being around animals. I’ve also worked as a dog and cat sitter, helping with walks, feeding, drop-ins, and overnights. I’m very reliable and pay attention to the little details so your pet feels comfortable and cared for. I have experience with puppies and senior dogs, can help with basic puppy training, and am comfortable giving medications if needed. I treat every pet like they’re my own and always try to make it a fun, positive experience, whether that’s a good walk, playtime, or just extra cuddles. I have a flexible work schedule and am able to fit pet care easily into my day. I’m available for walks, drop-ins, and some overnights (around my kids schedules), and make sure pets are cared for on a consistent schedule. I’m reliable and always plan ahead so your pet gets the attention and routine they’re used to. I always follow the owner's instructions closely, make sure collars/leashes are secure, and pay attention to any specific needs or behaviors. I’ll also keep you updated so you know your pet is safe, happy, and well cared for while you’re away. On walks I always pay attention to my surroundings to keep your dog safe. I'm not there to pay attention to your beloved dog, not get distractes by my phone or anything else.

Sitter Profile Image: Adam P.
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Adam P.
from
$17
per walk
20 years of experience
Chester, CT, 06412

About: Labradoodle Specialist. I’m a lifelong dog owner who genuinely enjoys spending time with animals. I provide attentive, reliable walks tailored to each dog’s pace and personality, with patience for puppies and gentle care for older dogs. I run a tech company from home, which gives me a flexible schedule. Dog walking fits perfectly into my day as a way to get outside for mid-day exercise while giving dogs the attention and activity they need. I prioritize safety, secure leashing, and awareness of surroundings. Walks are tailored made to each dog’s pace, with plenty of attention, care, patience and love.

Sitter Profile Image: Ileana S.
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Ileana S.
from
$25
per walk
8 years of experience
Deep River, CT, 06417

About: I’ve had dogs my entire life and have been dog sitting and walking for the past 8 years. I’m comfortable caring for dogs of all ages, sizes, and temperaments, including puppies and senior dogs. I’m attentive to each dog’s unique needs, whether that’s sticking to a routine, providing exercise, or offering extra patience and care. I treat every pet like my own and prioritize their safety, happiness, and comfort at all times. I have a flexible schedule and am able to dedicate plenty of time and attention to your pet. I’m available for walks, drop-ins, and boarding on weekends, as well as weekday afternoons and evenings. I make sure each pet gets the exercise, playtime, and care they need, and I’m happy to accommodate specific routines or requests whenever possible. I provide a safe, clean, and loving environment for every pet in my care. I have experience with dogs of different personalities and needs, and I always prioritize their safety and well-being. I follow any instructions closely, including feeding schedules, medications, and routines. I also make sure pets feel comfortable and secure, whether in my home or a client’s home, and I keep owners updated for peace of mind.

Sitter Profile Image: Jade G.
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Jade G.
from
$25
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
East Lyme, CT, 06333

Last minute booking very helpful !

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Kelly T.
Sitter Profile Image: Vincent G.
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Vincent G.
from
$20
per walk
5.0 out of 5 stars
73 reviews
19 repeat clients
10 years of experience
Clinton, CT, 06413

Vincent was wonderful with my pups! He responded quickly to my request and the girls loved him. He is very in-tune with the pups. Thank you Vincent!

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Dannon R.
Sitter Profile Image: Cayton M.
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Cayton M.
Star Sitter
from
$28
per walk
5.0 out of 5 stars
140 reviews
58 repeat clients
10 years of experience
Old Lyme, CT, 06371

Cayton was terrific. My dog is normally very anxious and she was wonderful with Lucy. They went on a nice long walk and Cayton sent me pics and lovely feedback. This was their first walk together but there will be many to come!

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Maris W.
Sitter Profile Image: Delaney B.
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Delaney B.
from
$15
per walk
10 years of experience
Westbrook, CT, 06498

About: I’ve been around dogs all my life, but started caring for them on my own since I was 10 years old. As I got older, I was around cats more and more, and now I have a great love for both pets!! My experience includes walks, potty breaks, playtime, overnighting with pets, senior care, and caring for high energy dogs. I often work on the weekends and Wednesday nights, but like to stay busy during the week. Staying busy mostly means being active and running errands. Pet care is a perfect opportunity for me to fill in the gaps! I will visit the pets as much as needed, feed them when advised to, pet them and play with them, and take them on nice, relaxing walks.

Sitter Profile Image: Sarah J.
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Sarah J.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
30 years of experience
Old Lyme, CT, 06371

About: I treat every pet as if they were my own. I take time to learn their routine, personality, and what makes them comfortable. I’m very dependable and I know how important communication is, I’m happy to send photo updates during visits so you can feel confident your pet is safe, happy, and well cared for. I’ve had animals in my life since I was five years old and have cared for a wide variety of pets over the years. I’ve always had my own dogs and cats. I’m very comfortable with different personalities and care routines. In my thirties I also worked with dog rescues, helping care for and support dogs in transition. While I stepped back from rescue work when my daughter was young, my love of animals has always remained a big part of my life. Because of this background, I’m very patient and attentive and understand that every pet has their own temperament and needs. I currently have a flexible schedule, which allows me to give pets the time and attention they deserve. Pet care fits naturally into my daily routine, and I’m available for morning, midday, and evening visits depending on your pet’s needs. Because I keep my schedule manageable, I’m able to be reliable and consistent with visits, walks, feeding times, and playtime. I enjoy spending time with animals and make sure each pet gets individual attention and care. I’m happy to work with owners to accommodate their pet’s normal routine and can often be flexible with scheduling when needed. Your pet’s safety and comfort are always my top priorities. I take the time to understand each pet’s routine, personality, and any special instructions so they can feel secure and cared for while you’re away. When caring for pets in a client’s home, I respect both your pet’s routine and your home. I make sure doors, gates, and leashes are secure during walks and outdoor time, and I closely supervise pets to keep them safe. I’m attentive to behavior, appetite, and energy levels and will contact you right away if anything seems unusual. I’m happy to follow any detailed instructions you provide—feeding schedules, medications, exercise needs, or special care. I also send regular updates and photos so you can relax knowing your pet is happy and in good hands. Having had animals my entire life and experience working with rescues, I understand how important trust is when someone is caring for a beloved pet.

Sitter Profile Image: Amanda B.
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Amanda B.
from
$20
per walk
20 years of experience
Ivoryton, CT, 06442

About: I have had all sorts of pets since I was a kid from bunnies, guinea pigs and hamsters to dogs and cats. I have a dog of my own. She is a sharp-eagle. She is about 2 years old and loves all dogs. I would love to bring her along with me to go on walks etc at your approval. I am currently a nanny part time and a part time student at SCSU. I would have plenty of time to care for your furry friend on the weekends. I care for your pets in your home and will follow any directions for caring for your furry friend. Whether its feeding and or playing or walking I am there to care for your pet in the time of need.

Sitter Profile Image: Roger B.
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Roger B.
from
$25
per walk
5.0 out of 5 stars
90 reviews
14 repeat clients
28 years of experience
Westbrook, CT, 06498

Roger clearly loves dogs - he became instant friends with our little Maltipoo Brody. Roger was dependable and friendly, and we were lucky to have found him. Highly recommended as a dog walker!

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Lee S.
Sitter Profile Image: Julianne Y.
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Julianne Y.
from
$17
per walk
5.0 out of 5 stars
30 reviews
7 repeat clients
8 years of experience
Middletown Ct, CT, 06457

Julianne is wonderful & it’s been such a relief to know that my dog is getting out for a walk. She’s reliable and always sends me pictures of my dog on the walk!

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Marcy N.
Sitter Profile Image: Frances P.
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Frances P.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
40 reviews
12 repeat clients
30 years of experience
East Haddam, CT, 06423

About: I have loved animals my entire life. I currently have 7 dogs and 1 cat of my own and foster frequently. I volunteer yearly at an animal sanctuary in UT. I transport dogs and cats for rescues. I have participated in many dog/puppy training classes and would continue any training programs for you while your baby is in my care. I will dispense medications and follow any medical instructions necessary. I am currently retired and love to hike and walk. I have an open schedule in the mornings and afternoons 7 days a week to care for your fur babies. I’m sure they would love to join me on a walk or hike. I have 7 dog friendly dogs that romp at my 2 acre property. My home is often referred to by friends as “Fran’s Dog Park” as visiting dogs are always welcomed. My two cats have learned to tolerate the dog infestation

Sitter Profile Image: Beverly T.
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Beverly T.
from
$17
per walk
20 years of experience
Haddam, CT, 06438

About: There has literally been zero times in my life that I did not own some kind of pet. I sincerely like being around any type of animal and their health and well-being and happiness is always at top priority. Currently, I have an open schedule to fit the needs of any routine. From just drop ins to over nights I can accommodate anyone’s needs. my home or yours. Safety and comfort are always the most important. I am extremely flexible and open to whatever is needed. Compassionate and caring 100% of the time.

Sitter Profile Image: Paul O.
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Paul O.
from
$25
per walk
40 years of experience
East Haddam, CT, 06423

About: Hello! I’m Paul, a retired professional with over 40 years of experience in caring for pets of all kinds—from champion lines to rescue breeds. My lifelong passion for animals has led me to start a pet sitting and walking service. I believe every pet deserves love and care, and I am committed to providing the best experience for your furry family members. Let me help keep your pets happy and healthy while you’re away. Pet care is a delightful part of my daily and weekly routine. Mornings start with energizing walks, afternoons are spent providing attentive care, and evenings are reserved for relaxation and enjoying quality time with family. Committed to providing a safe and secure environment for your pets during walks. Ensuring their safety with careful supervision, proper leash handling, and adherence to all safety protocols.

Sitter Profile Image: Sierra J.
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Sierra J.
from
$20
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Old Saybrook, CT, 06475

About: I've taken care of aniamls since I was 3, I take of my friends and neighbors animals, to give feed them and walk them and bathe them. I don't work because I live on a small farm and take care of them and all my dogs and birds and cats and I can work with anyone's pets after school. I have a dog fence with a doggy door for in and out and it's all fenced in and I have very friendly dogs that will Play and keep company.

Sitter Profile Image: Abbey B.
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Abbey B.
from
$25
per walk
5.0 out of 5 stars
4 reviews
18 years of experience
Essex, CT, 06426

About: Greetings! I have grown up with dogs all my life and love the bond shared with each pet I interact with. I have cared for a variety of different breeds and types of pets and dogs. I am an energetic and caring dog lover that takes pride in every animal that crosses my path. I am very reliable and have a flexible schedule. I pride myself on being responsible and professional. When interacting with your furry friends l'll be sure to give the love and care they deserve and you expect! I am currently a student with flexible work schedules as I am working mainly at home for right now. I am able to work most of the week/weekends during a variety of times. I am very reliable, and make your pet and you a priority! I pride myself on being responsible and professional. I treat every pet and home like it was my own and always maintain a certain level of respect and trust for anyone’s home or pet. When interacting with your furry friends I’ll be sure to give the love and care they deserve and you expect!

Sitter Profile Image: Brian W.
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Brian W.
from
$20
per walk
15 years of experience
Deep River, CT, 06417

About: I've taken care of many dogs and have had my owns dogs and cats. I have great patience with animals and have trained several dogs. I have a 9-5 job but am free most of the other times. If you are near Essex I can leave work and take dogs out midday as well. I love playing with cats and dogs and keeping them entertained as well as exercised. I can walk your dog for miles if that is what they like.

Sitter Profile Image: Erin G.
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Erin G.
from
$25
per walk
1 repeat client
25 years of experience
Essex, CT, 06426

About: I have taken care of a huge variety of animals in my career and I am very good with animals. For a very long time my friends have relied on me to provide the best care for their beloved pets. I am currently working part time and would like to make the pet care service my full time career! I will have plenty of time to spend with your pet and I will do my best to provide the best care possible! Working with large animals my whole career I am extremely diligent about safety for all animals. I will put your pet's safety as a first priority.

Sitter Profile Image: Darcy A.
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Darcy A.
from
$30
per walk
5.0 out of 5 stars
24 reviews
10 repeat clients
25 years of experience
EAST HADDAM, CT, 06423

Darcy is great with my 2 girls! On nights when I work late it's awesome to get some cute pics during the middle of the day letting me know they got out and had some fresh air. I could tell immediately she was a true dog lover! Very quick to answer any messages I send, checks they have water before she leaves, and always sends me a report of what they did that day as well as multiple pictures ☺ thank you so much Darcy!

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

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Popular requests for dog walking - Chester

Select a filter and find qualifying sitters offering dog walking.

Sitters in Chester average 3
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 $38.85 per walk (as of August 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 August 2026, there are 2,337 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
  • 98% 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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