Dog Walking Cheshire

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

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Over 69
pet parents in Cheshire have booked dog walking

Cheshire, 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: Erin M.
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Erin M.
from
$17
per walk
5.0 out of 5 stars
5 reviews
40 years of experience
Wallingford, CT, 06492

About: I have been owned by cats my entire life and have taken care of dogs of all kinds for family and friends for years. I am comfortable with giving medication to cats, including insulin shots. I've had 2 diabetic cats. I am also a Reiki Level 2 practitioner and can give reiki to pets. I have always been the go to pet sitter for my family and friends when they go on vacation. I'm known as the animal whisperer and can usually win over any animal! Just a quick note that my evening visit window ends at 7pm. If you need a later time for a drop-in visit, please mention it before booking so we can confirm whether it is possible. Thanks! I am a home healthcare worker so I have a flexible schedule. I usually finish for the day between 2:30 and 3:30 and am available after that. I can be available during the work day (9-3) with advanced notice to schedule patients around pets! I can also be available some mornings earlier than 9 with advance notice. I will happily come to your home and play with and feed your cats and dogs. I will also walk your dogs and claen up after them. I am willing to give medication if necessary as well.

Sitter Profile Image: Susan B.
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Susan B.
from
$20
per walk
4.9 out of 5 stars
10 reviews
4 repeat clients
40 years of experience
Cheshire, CT, 06410

Susan was so great with my very old dog. She was patient with him and even carried him up the steps when necessary. Susan always arrived when scheduled. I will definitely be using her services again.

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Lynn D.
Sitter Profile Image: Darya H.
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Darya H.
from
$21
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Prospect, CT, 06712

Darya was amazing! Kept in touch and sent lots of pictures! I will definitely be using her again 😊

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Jaime W.
Sitter Profile Image: Hailey T.
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Hailey T.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
79 reviews
23 repeat clients
10 years of experience
Meriden, CT, 06451

Hailey did a fantastic job coordinating and helping walk our energetic puppy! Always responsive and helpful give feedback and ensuring our puppy was happy and had a great time!

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Michael D.
Sitter Profile Image: Julie R.
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Julie R.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
65 reviews
27 repeat clients
20 years of experience
Meriden, CT, 06451

Julie has been amazing with my dog, Cooper. She’s been doing his mid-day walks and has been incredibly reliable and flexible, which I’ve really appreciated. She’s been easy to communicate with and very accommodating with my schedule. Honestly, I’d keep working with her without hesitation if I weren’t moving. Would definitely recommend her to anyone looking for someone trustworthy to take care of their dog.

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Michael M.
Sitter Profile Image: Lori C.
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Lori C.
from
$17
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
25 years of experience
Cheshire, CT, 06410

About: I’ve cared for dogs and pets for over 25 years and truly love being around animals. Friends and family have trusted me to help care for their pets because I’m calm, dependable, attentive, and patient. I understand how important it is to feel your pet is safe, loved, and comfortable while you’re away, and I treat every animal with kindness and care as if they were my own. I’m currently working part time and have a flexible schedule. Pet care fits easily into my daily routine because I truly enjoy spending time with animals. I have a calm, caring home and love walks, outdoor time, companionship, and giving pets the attention and affection they need to feel safe and happy. I provide a calm, safe, and loving environment where pets can feel comfortable and secure while their owners are away. I pay close attention to each pet’s routine, personality, and needs, including feeding schedules, walks, playtime, medication if needed, and plenty of affection and companionship. I understand how important trust is when someone is caring for your pet, and I treat every animal with patience, kindness, and the same care I would want for my own.

Sitter Profile Image: Olivia H.
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Olivia H.
from
$16
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
6 years of experience
Cheshire, CT, 06410

Good communication, very friendly Oscar loves her.

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Christopher K.
Sitter Profile Image: Alexandra C.
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Alexandra C.
from
$25
per walk
14 years of experience
Cheshire, CT, 06410

About: Grew up with four dogs and lifelong pet care experience. Trusted by clients & friends. Skilled with French Bulldogs and Dachshunds, including IVDD-aware handling. Attentive, reliable, communicative! Pet care easily fits into my routine. I have a flexible schedule and am available any day, ensuring pets receive reliable, attentive care whenever needed. I carefully follow each owner's instructions, maintain pets' routines, provide plenty of attention, exercise, feeding, medication if needed, and keep their home clean and secure.

Sitter Profile Image: Rebecca F.
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Rebecca F.
from
$25
per walk
5.0 out of 5 stars
25 reviews
11 repeat clients
20 years of experience
Wallingford, CT, 06492

We don’t have a very easy dog to walk but Rebecca did a great job making him feel comfortable and get plenty of exercise and time outside! She gave us great feedback on ways to help in the future with a scared stressed dog and we will definitely have her walk our dog in the future!

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Michael D.
Sitter Profile Image: Christine W.
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Christine W.
from
$10
per walk
5 years of experience
Cheshire, CT, 06410

About: While I don’t have experience walking other’s dogs, I’ve owned two, both large and medium, and I have many years of experience walking and taking care of dogs. With it currently being summer, I’ve had a very flexible schedule. It would be very easy for me to add pet care to my routine. As a dog owner, I’m familiar with how important walking is in my dog’s daily routine as much as it is for me. I, myself, am a dog owner to both a large and medium dog at some point. Exercise, especially for larger dogs, is extremely important. I take my dog for a walk almost every day in order to insure her health.

Sitter Profile Image: Sara R.
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Sara R.
from
$18
per walk
5.0 out of 5 stars
12 reviews
5 repeat clients
10 years of experience
Prospect, CT, 06712

Sara was awesome!! She came literally with an hour notice and my dog enjoyed her walk with her. Definitely recommend & will book again in the future. Thank you!

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Lusianna M.
Sitter Profile Image: Mary M.
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Mary M.
from
$23
per walk
5.0 out of 5 stars
18 reviews
9 repeat clients
40 years of experience
Wallingford, CT, 06492

Mary has done an excellent job. She shows up on time and gives our dog a nice walk. He seems glad to see her on those occasions when my wife was home at walk time. Happy to suggest her to others.

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Richard L.
Sitter Profile Image: Tatum D.
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Tatum D.
from
$20
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Meriden, CT, 06451

About: My name is Tatum I am 20 years old and have had exotic pets such as birds reptiles bugs and more. I currently have my own dog her name is Ripley and she’s almost a year old pit being trained for obedience and heel work I have training experience and dog care experience as I also used to work at a pet store caring for over 60 puppies at a time cleaning feeding playing with and giving medication! I currently am full time looking to fill up my schedule taking care of everyone’s animals feel free to ask questions and more ! Thank you I offer walks over night stays and I can do training and enrichment activities with your pup ! I’m also experienced with giving medications to sick dogs or seniors if needed

Sitter Profile Image: Hunter D.
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Hunter D.
from
$22
per walk
4 years of experience
Cheshire, CT, 06410

About: I've taken care of dogs since I was a freshmen in high school. My jobs consisted of walking, feeding, playing, and occasionally staying overnight with the dog. I love animals and genuinely care for them, making my service just a bit more special. Currently I only work after 3:45 on weekdays, so I have plenty of time to hangout with your pups! I have enough time for attentive care and multiple visits per day! I do not intend to board any dogs in my home, but I can crate a dog, I am comfortable with fenced in backyards for unleashed pups, and when no fence is available the dog will be leashed/harnessed.

Sitter Profile Image: Millie S.
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Millie S.
from
$20
per walk
1 year of experience
Wallingford, CT, 06492

About: I’ve always loved animals and currently care for my own Yorkshire Terrier puppy, Molly. Being a pet owner has taught me the importance of patience, consistency, and paying close attention to a dog’s needs. As a college student and part-time employee, I am responsible, dependable, and committed to making every walk safe, fun, and enjoyable. I will treat your dog with the same love and care I give my own I’m currently a part-time employee and a college student, which gives me flexibility to provide reliable pet care. I’m available for dog walks during my free time, including evenings, weekends, and many weekdays. I always make sure each pet receives plenty of attention, exercise, and care during every visit. Your dog’s safety is my top priority. I always keep dogs securely leashed during walks, follow each owner’s instructions carefully, and provide fresh water if needed. I pay close attention to each dog’s behavior and avoid unsafe situations. I treat every pet with patience, kindness, and the same care I give my own dog.

Sitter Profile Image: Victoria S.
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Victoria S.
from
$20
per walk
5.0 out of 5 stars
13 reviews
7 repeat clients
10 years of experience
Cheshire, CT, 06410

We couldn’t be happier with Victoria! From day one, her communication has been clear, timely, and thoughtful—keeping us updated with photos and messages every walk. Her professionalism truly stands out, and it’s clear how much she cares. As a sweet bonus, she even made homemade treats and gave us a special doggy bag as a thank-you for trusting her with our pup. It’s rare to find someone so reliable and kind—we highly recommend her!

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Jared C.
Sitter Profile Image: KELLY G.
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KELLY G.
from
$22
per walk
5.0 out of 5 stars
1 review
1 repeat client
30 years of experience
Meriden, CT, 06450

Happy Fourth of July Kelly thanks for all you do

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Christopher J.
Sitter Profile Image: Christopher C.
Verified Enhanced Background Check
Christopher C.
from
$30
per walk
5.0 out of 5 stars
38 reviews
11 repeat clients
15 years of experience
Chesire, CT, 06410

Chris helped us out by walking our two giant dogs for a week while we had a newborn baby to take care of at home. He was super communicative, always on time, and sent lots of updates and photos! Our dogs were SO excited to see him every morning. We will definitely be using him again!

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Natalie D.
Sitter Profile Image: Sabrina H.
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Sabrina H.
from
$25
per walk
5.0 out of 5 stars
42 reviews
19 repeat clients
8 years of experience
Meriden, CT, 06451

Sabrina is great! Very easy to schedule and communicate with, and my dogs lover her!

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Ann C.
Sitter Profile Image: Angela B.
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Angela B.
from
$38
per walk
4.8 out of 5 stars
59 reviews
29 repeat clients
10 years of experience
Cheshire, CT, 06410

Angela is great. She was able to come take care of our puppy on very short notice, and sent us updates throughout the day. We'll definitely be contacting her again!

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Alicia D.
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The median cost per walk for dog walking in Cheshire is $22

Dog parents share their Rover experiences - Cheshire

1 / 1
5.0 out of 5 stars

Absolutely fantastic with communication and updating me throughout the time of us being away. I would 100% recommend her.

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Annmarie H.
Dog Walking
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  • 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?

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  • 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

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Popular requests for dog walking - Cheshire

Select a filter and find qualifying sitters offering dog walking.

Sitters in Cheshire average 3
repeat dog walking clients

FAQs for Dog Walking - Cheshire

Frequently asked questions about Rover

The average cost for Dog Walking in Cheshire on Rover is $21.4 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 2,921 sitters on Rover offering Dog Walking across Cheshire. 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 Cheshire. 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 Cheshire.

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 Cheshire. On Rover:

  • 92% of walkers can help with special care needs
  • 95% 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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