Dog Walking Chesterfield
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Chesterfield, 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.
About: I love all animals and have fostered for the local Humane Society for the last couple of years. I am drawn to all animals regardless of type, size or breed. Sometimes the more unique the better but there’s something special about every pet. I work remotely so my schedule allows flexibility that is conducive to pet sitting. I am available 7 days a week. I can sometimes accommodate last minute bookings as well. I work remotely and love getting out for walks. I have a flexible schedule but I also know how hard it can be to entrust someone with your fur babies so I am happy to answer any questions you may have.
“Mila walked Kiki on such short notice and was extremely professional during our meet and greet! Kiki is very excitable with new people and it was nice to see her calm and relaxed during a first meeting :) we look forward to future walks and dog sitting!”
About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.
“Michael is an amazing dog walker for Theo. He is always available for us, even if it’s only a day or so warning and Theodore absolutely adores him. He sends photo updates to me which makes me so happy to see Theo when I’m gone from work! Thank you Michael!!!”
About: I have over 10 years of pet care experience including walks, overnight stays, and short visits. I also grew up with dogs and have lived with a few different cats in my adult life. I am new to the Rover app but am happy to provide references upon request. I work Monday-Friday 11-5 in Brattleboro. I can do overnights any day of the week, but just know that on these days I will be away for 6-7 hours depending on distance from your house. I love taking dogs on long walks and can do so 2-3 times a day. I am super communicative and experienced at house sitting while pet sitting. I am very respectful of people's homes and pets' routines. I will make sure to keep your house as clean - and your pet as happy - as you left them.
About: I’ve taken care of dog of many sizes and health conditions, I have had a cat for 9ish years and have cared for friend and families dogs for years. I am a student, I am relatively free but lots of work to do! I like to go on walks already! I am able to be flexible. I know how to feed animals and care for them, can follow special instructions as I know they are important. As much as I would love to care for your fur baby at my home, I cannot.
About: Hi, my name is Layton and I've been an animal lover my whole life. I've had furry family members since I was five years old and multiple re-occuring caretaking jobs, so I know how to care for your baby. From 2018 to 2020 I worked as a dog groomer and had the privilege to work with pups of all kind - big, small, young, old, excitable and laid-back. I especially love to provide YOU with a sense of comfort knowing that your pet is in wonderful hands. I am available for overnight sittings, drop-in visits, walks, trips to the dog park and even transports to the vet and groomer. Just let me know what kind of care your pet(s) need and I'll be there! I currently have a pretty flexible schedule for the time being. I am willing to take on weekly walks, occasional overnight sittings and longer term stays. I do not offer care at my home (I live with two cats that are not too fond of other animals). But, I can provide meals, walks, play and love for your pet in their own home!
About: Ive been taking care of pets since high-school, from great danes to kitties! Including but not limited to great-danes, pitbulls, hounds, labs and kitties! I am good with animals of all temperaments, from timid and not sure to excited to see anything! I love all animals and would love to help with all your pet and house needs. I am currently part time and can work around your schedule as well. I already get up to take care of my hound, pitbull and kitties. I would love to help you out as well! I love animals and have experience with the animals that also make a mess. I change litter boxes and I can even clean up after the ones who can't always hold it. I feed, and give fresh water. I walk dogs and also have experience with pulling. I can also just let them out if trained to do so and hangout with them as needed!
“Damien went above & beyond walking Louis for close to an hour and even hung out a bit upon their return. I know he cares for other people’s pets like his own!! Much appreciated.”
“Brandy is now my Rover person of choice. She was early to pick up Sophie; gave her a fun yet rigorous workout. And, when she came back, Brandy ensured her paws were clean so she didn't track mud into the house. Sophie adores her as do we. She's the best.”
“I had a work trip and Haley was such a big help walking our pup for the week while I was away. She was very communicative, accommodating, and sent updates everyday. We would definitely ask for her help to care for our pup in the future!”
About: I’ve taken care of senior cats that need lots of care like hand feeding or needing help with litter box. I’ve walked lots of different dogs. I have a 2yr old female gentle potcake. I will be walking your dog with her. I like to take dogs off leash for runs. I’m self employed and work from home here in Walpole. The highlight of my day is walking my neighbors dogs. It would be easy to fit other dogs into my walks or stop by to check in your cat or dog. I’m reliable, kind, generous and trustworthy. I would care for your pet with the same care I would provide my own. I’m not into forcing pets to do anything. Having their participation in any activity is a must.
About: Each pet has their own personality and style and I adapt to exactly what your pets need and want. If they want cuddles, they get cuddles. If they want space, they get space. It's all about the precious pets needs for me. I provide 5 star service and have a flexible schedule to meet your and your four legged friends needs! I don’t have a furry friend of my own but I love the opportunity to give a little love to all the pets I meet. Any dog big or small is awesome in my book. My aim is to make them happy and your life a bit easier! I look forward to hearing from you and getting to spend time with your wonderful pets! I currently work a 9 to 5 remote job and have plenty of flexibility to meet you and your pets needs. I can house sit or do drop ins as needed with my schedule. I am the happiest when I am around dogs and enjoy playing with them! I have been the go to dog sitter for my friends and family for over 8 years. I have access to trails in my backyard and live and work in a dog friendly area. I love meeting new friends and having fun adventures around our gorgeous town.
“Lilly was great to work with, as well as reliable and responsive to a small last l-minute adjustment. I loved getting the photos of Trina. I will definitely ask Lilly to care for Trina again!”
“Jeffrey is amazing! He was on time, personable and professional. He was patient with my dog and now Finn runs right away to Jeffrey. Rover is lucky to have him! As are we!”
About: I have been working as a veterinary assistant for 3 1/2 years. I am experienced in giving oral and injectable medications. I love dogs and cats of any size! I currently work 3 1/2 days a week and I’m doing pet care on my days off. I love spending my time meeting and taking care of new pets! I treat every pet like they are my own. I always send updates to the pet parents throughout my visits so everyone can be stress free!
About: I’ve been around animals since I was 8. I’ve fostered animals, and helped walk, feed, bathe, supply medicine (supplements and pills) to them for friends, family, etc for a little over 8 years now. I’m very experienced with younger dogs and can provide extensive walks / playtime for entertainment and engagement. I also love working with senior dogs as well, and can help provide a calm, stress free environment for them while their owner is away. I’m currently working part-time from home and have a very flexible schedule! I can do drop in visits, overnight stays, and even long weekends / weeks for vacations and getaways! Early mornings and late nights are no problem for me as well. I don’t mind cleaning up messes or puddles, and I can travel very flexibly if needed! I am OK helping with crate training, and providing a positive environment for any pup to grow in while their family is away! I have a fur baby of my own who is almost 4 years old, and absolutely adores other dogs! He is neutered, house trained, and very relaxed. He has been a very good role model for our youngest puppy in the house.
The median cost per walk for dog walking in Chesterfield 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.
Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog walking - Chesterfield
Select a filter and find qualifying sitters offering dog walking.Sitters in Chesterfield average 4 repeat dog walking clients
FAQs for Dog Walking - Chesterfield
Frequently asked questions about Rover
As of September 2026, there are 344 sitters on Rover offering Dog Walking across Chesterfield. 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 Chesterfield. 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 Chesterfield.
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 Chesterfield. On Rover:
- 88% of walkers can help with special care needs
- 97% 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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