Dog Walking Chesterfield

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

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Over 4
pet parents in Chesterfield have booked dog walking

Chesterfield, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Janet M.
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Janet M.
Star Sitter
$34
total per walk
4.9 out of 5 stars
• 19 reviews
9 repeat clients
53 years of experience
Chesterfield, MA, 01012

“Janet is very responsive to msgs, shows up at the scheduled times, and provides summaries of her visit. Thanks Janet!”

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Allen B.
Sitter Profile Image: Shawna B.
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Shawna B.
$35
total per walk
5.0 out of 5 stars
• 9 reviews
4 repeat clients
15 years of experience
Westhampton, MA, 01027

About: I have taken care of family and friends pets (cats and dogs) for many years and have regular clients for pet sitting and dog walking. I have had my own pets as well for most of my life. I have fostered many cats through a local animal shelter and have volunteered with a local organization to walk dogs. I have completed a Pet Sitter and Dog Walking Certification. I will treat your pets as I do my own and will provide loving care and I will ensure that your requests are met for your pet. I am organized and trustworthy and am available for pet sitting in my home, drop in visits and some house sitting. I am available on weekends and weekdays depending on the request. I work from home so if your pet is staying in my home I am able to let them out as needed (for dogs) and provide lots of loving attention throughout the day. Depending on the service-Boarding/pet sitting is provided in my home. We have a big yard and trails in the woods so dog walking is easy and enjoyable. Drop in visits can be set up at your home for cats or dogs as well.

Sitter Profile Image: Kristin B.
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Kristin B.
$56
total per walk
5.0 out of 5 stars
• 17 reviews
4 repeat clients
20 years of experience
Goshen, MA, 01032

About: Have owned dogs for over 20 years, pet sit for friends, family, and neighbors. I am over cautious and protective when it comes to animals, I'm also active so love walking dogs, throwing a ball for them, or taking them to our local lake for a swim. I have tons of patience for shy dogs, I have dealt with rescue dogs and know when to get close or not to an animal. I have never had an incident where I have had a dog become aggressive with me. I have taken my own dog to obedience school a few times and learned a few key trips for working with difficult dogs or puppies. I have taken care of puppies within the past three years and am comfortable with the extra care they require. I have a solid connection with our local vet and emergency animal hospital and am able to handle dogs who need shots or medications administered. I work from home and have several pets already needing care. Bathroom breaks, walks, ball throwing, catnip time, all of it already happens in my home. We have several pet fences within our home and a puppy proof first floor. If a pet is okay of leash then we walk them around our 4 acres throwing a ball or whatever the pet likes. If a pet is not okay off leash, then we just walk them on a leash on our land every 1.5 or 2 hours or as needed. Water bowls are everywhere, no chemicals are on site within reach of curious puppies, and no cars move very quickly on our driveway and everyone who does arrive at our home knows we have several pets and need to slow down. We have owned dogs for over 25 years and have never had any of our pets get injured.

Sitter Profile Image: Amanda C.
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Amanda C.
$34
total per walk
60 years of experience
Florence, MA, 01062

About: I have taken care of animals since I was little. Home pets mostly. But also my neighbors dog. I love any kind of animal Cats, dogs, bunnies, birds all!! I am currently retired and am free most days and nights. I have 2 grandchildren and big helpers! But if not comfortable with that please let me know I have an un fenced yard and 2 very friendly dogs, I would be willing to stay at your home or bring them my way

Sitter Profile Image: Evan A.
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Evan A.
$34
total per walk
5.0 out of 5 stars
• 7 reviews
10 years of experience
Florence, MA, 01062

About: I'm available for all holidays starting with Thanksgiving, Christmas, Hanukkah, Kwanza and New Year's Eve I'm a lifetime pet owner and pet sitter with strong references 🙏 I'm not employed by anyone else, so my time is wide open and I live on a quiet dead end street and close to regular parks and dog parks / trails. I always take the owners preferences seriously, but I do like to spoil with good food and treats. I also am good with grooming calmingly.

Sitter Profile Image: Amad E.
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Amad E.
$28
total per walk
5.0 out of 5 stars
• 34 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

About: I've been house and pet sitting for ten years plus, besides that I've been an owner of many dogs and cats. There is nothing that makes me happier than the well-being of them. When you choose me for the care of your fur babies, they'll be taken care of to the maximum comfort and standard. I'm flexible in that I work remotely... So i huge amount of the time i will be around to cater to your pets. And also will be able to walk them often and keep them stimulated I'll make sure their safety and the environment they're in are safe and nurturing. If it's the owner's house I won't change a thing, if it's my house I'll have them have access to all that they would have at their home.

Sitter Profile Image: Leona O.
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Leona O.
$20
total per walk
4.8 out of 5 stars
• 13 reviews
3 repeat clients
10 years of experience
North Adams, MA, 01247

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.

Sitter Profile Image: Jessica M.
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Jessica M.
$28
total per walk
5.0 out of 5 stars
• 19 reviews
4 repeat clients
10 years of experience
South Hadley, MA, 01075

About: As a child, I owned almost every pet imaginable - from house cats to Rottweilers to lizards to ferrets! Bless my poor mother's heart - we practically had a small zoo at our house! As an adult I owned a cat for 5 years and also "dog /cat sat" for friends and families many times. I'm an all-around animal lover who is comfortable with many different types of pet care. I'm a stay-at-home mom with a four year old. Please be advised that if I pet-sit overnight at your home, my daughter will most likely be accompanying me for at least part of the job assignment. If you aren’t comfortable having well-behaved, well-supervised children at your home, then unfortunately I’m not a good fit your you. I have plenty of flexibility on both weekdays and weekends to provide care for your pets. I live in a pet-friendly house with a fenced-in back yard. The neighborhood is quiet and safe for walks. I also have access to a nearby park.

Sitter Profile Image: Lilly T.
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Lilly T.
$34
total per walk
5.0 out of 5 stars
• 11 reviews
3 repeat clients
19 years of experience
Belchertown, MA, 01007

“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!”

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Susanne P.
Sitter Profile Image: James M.
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James M.
$34
total per walk
5.0 out of 5 stars
• 73 reviews
19 repeat clients
5 years of experience
Boston Road, Springfield, MA, 01119

“Thank you for the great communication and taking such great care of our Cooper!”

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Allison L.
Sitter Profile Image: Sydney D.
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Sydney D.
$38
total per walk
20 years of experience
Southwick, MA, 01077

About: I’ve been an animal lover for as long as I can remember! I grew up with Labs, so I’m very familiar with big personalities, lots of energy, long walks, playtime, and plenty of slobbery love. 🐾 I also adopted a cat, which taught me that sometimes the best way to win a pet over is to let them come to you (and maybe offer a few treats!). Although my own pets have since passed, they gave me years of experience, amazing memories, and a genuine love for caring for animals. I’m patient, playful, attentive, and always focused on making pets feel safe and comfortable. Whether your pet wants an adventure outside, a game of fetch, or just some extra love and company, I’m happy to be their new buddy while you’re away! ❤️ I currently own my own business and make my own hours and work from home, so I can easily make my own schedule fit around any pet care! I'm lucky to have an open, comfortable and clean home where I can walk animals on the many acres I live on. I can also crate animals if that's how they are trained. When in other people's homes, I'm incredibly conscious of being considerate, following directions to respect their space, and understanding how the animal uses and loves the space.

Sitter Profile Image: Tayo F.
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Tayo F.
$12
total per walk
4.0 out of 5 stars
• 2 reviews
3 years of experience
West Hartford, CT, 06110

About: I've helped family members with their dogs since I was 7, spent months working 11 hours a day at dog training school, and recently, my home has become a second house for a little Scottish terrier named 'Zoe.' and for a few years, we've been taking care of her, and her owner has been happy to send her back again and again. I am very flexible, I can work any day as I love taking care of pets and knowing they are as happy and safe as they can possibly be. I am not able to host dogs in my home, however, when taking care of a dog in your home, I would be willing to feed, walk, bathe or play with them in exactly the preferred way.

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The median cost per walk for dog walking in Chesterfield is $23

Dog parents share their Rover experiences - Chesterfield

1 / 1
4.0 out of 5 stars

Janet is very responsive to msgs, shows up at the scheduled times, and provides summaries of her visit. Thanks Janet!

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Allen B.
Dog Walking
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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

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Popular requests for dog walking - Chesterfield

Select a filter and find qualifying sitters offering dog walking.

Sitters in Chesterfield average 3
repeat dog walking clients

FAQs for Dog Walking - Chesterfield

Frequently asked questions about Rover

The average cost of Dog Walking in Chesterfield is $24 per walk as of October 2026. Most bookings cost between $24 and $34 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 890 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 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 Chesterfield 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 Chesterfield. On Rover:

  • 91% of walkers can help with special care needs
  • 92% 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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