Dog Walking Chesterville

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Chesterville, 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: Carolyn G.
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Carolyn G.
from
$25
per walk
5.0 out of 5 stars
1 review
45 years of experience
Galena, MD, 21635

About: I’ve had several dogs through out my life. I’m an animal lover. I’ve had Shetland sheepdogs and I currently have 3 English Bulldogs in my home. I have a very flexible schedule. I’m available to do multiple drop in visits throughout the day and night. I have weekday and weekend availability I do not offer pet care in my home. I am able to come to your home to care for your animals. Client home care only

Sitter Profile Image: Sabrina G.
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Sabrina G.
from
$25
per walk
4.6 out of 5 stars
32 reviews
9 repeat clients
15 years of experience
Chestertown, MD, 21620

Sabrina is always interacting with Peaches and has bri get her dogs to teach Peaches how to play.

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Jane Ann W.
Sitter Profile Image: Delaney M.
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Delaney M.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
31 reviews
11 repeat clients
9 years of experience
Dover, DE, 19901

Delaney is wonderful and Nala loves her. She is professional, polite, and always on time. Your pets will definitely be in good hands with her.

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Latanya A.
Sitter Profile Image: Heather C.
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Heather C.
from
$25
per walk
1 repeat client
3 years of experience
Georgetown, MD, 21930

About: I am new here and I am excited to begin this part of my journey! I am also a mother of 3 magical human beings, a shamanic reiki student, hospice companion and a volunteer at my local animal care shelter. Over the last few years I have been learning to live with chronic illness and I have found a lot of healing spending time with animals of all kinds. Mondays & Tuesdays I am available between 9:30AM - 2:30PM. Wednesdays through Fridays, I am also available in the morning and evening. Ask about weekends - I might have availability! It is my goal to lead with care, respect and play. I am a sensitive soul and I do my best to approach each pet gently and with consideration for who they are and what they need.

Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$25
per walk
5.0 out of 5 stars
26 reviews
12 repeat clients
8 years of experience
Townsend, DE, 19734

Great, as usual!

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Jeffrey s.
Sitter Profile Image: Busara C.
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Busara C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
84 reviews
12 repeat clients
5 years of experience
Dover, DE, 19904

Our Chance simply loves Busara and for great reasons!!

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Lynnell W.
Sitter Profile Image: Cameryn C.
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Cameryn C.
from
$20
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
6 years of experience
Clayton, DE, 19938

About: I have 6 years of experience taking care of 4 cats and my dog!! I can feed, give water, take walks, scoop boxes, and entertain with toys. I am also excellent with anxious pets and those who need a little extra care and love. I have a gentle voice and will always try to be aware of your pets' comfort level before approaching. I am currently in college, so I go to class various times during the week! Because of this, I may need to adjust arrival times depending on my class schedule and what days you need me for. This also means that I am good for vacations and other short-term jobs. I will work hard to provide a safe environment for all animals in accordance with guidelines set by my clients. For dogs, I prefer a fenced in yard, but will consider leashed walks depending on the size of your dog.

Sitter Profile Image: Robyn L.
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Robyn L.
from
$25
per walk
5.0 out of 5 stars
3 reviews
15 years of experience
Clayton, DE, 19938

About: With 10+ years of caring pets of all kinds—dogs, cats, and more—I treat every animal like my own. I bring patience, reliability, and always want to learn each pet’s quirks and needs. Whether it’s walks, playtime, basic training, or medication, I provide loving care with regular photo and text updates to keep you updated and connected. I have a flexible schedule! I’m open to any time, day, or length your pets need care. So house-sitting and overnights work great for me! I guarantee your pets will receive plenty of love, walks, and pets when I’m there. When caring for your pets, I will make sure to keep their routines as consistent as possible—from walks and activities to mealtimes and medicine. I respect your home and space by keeping it clean and secure so both you and your pets feel comfortable and safe. I also enjoy sending photo and text updates to keep you updated and connected!

Sitter Profile Image: Paul C.
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Paul C.
from
$20
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Elkton, MD, 21921

Paul and his fiancée do a great job with my Husky. My dog normally doesn’t enjoy other humans, and he loses his appetite when I travel. But Paul’s energy didn’t bring any of those concerns out.

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Andre J.
Sitter Profile Image: Ashley C.
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Ashley C.
from
$25
per walk
5.0 out of 5 stars
11 reviews
2 repeat clients
10 years of experience
Centreville, MD, 21617

I appreciated her flexibility and text/picture updates

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Meaghan K.
Sitter Profile Image: maranda c.
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maranda c.
from
$20
per walk
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Church Hill, MD, 21623

Great communication before and during booking

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Meaghan K.
Sitter Profile Image: Amarachi N.
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Amarachi N.
from
$35
per walk
5.0 out of 5 stars
2 reviews
20 years of experience
Middletown, DE, 19709

About: I have owned pets all my life and am an experienced pet owner, I’ve cared for pets with different personalities, routines, energy level and age ranges. I’m comfortable with long walks, drop in visits, feeding, medication administration, playtime, enrichment and following detailed instructions. I am also attentive, reliable and communicative and will always treat your pet and home with care and respect. I’m currently have a flexible schedule and offer drop in visits, dog walking and house sitting. I am available throughout the week and will do my best to accommodate your pet’s normal routine. As a pet owner I also understand communication and consistency matters, so I aim to be punctual, as communicative as possible and reliable. For walks, drop-ins, and house sitting, my goal is to make your pet feel safe, comfortable, and cared for in their own environment. I follow feeding instructions, routines, medication schedules, and activity preferences closely. I also pay attention to behavior, energy levels, and comfort cues and will always communicate any concerns. I treat clients homes with care and respect and will provide updates and photos for peace of mind while you’re away.

Sitter Profile Image: Josiah S.
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Josiah S.
from
$15
per walk
5.0 out of 5 stars
1 review
12 years of experience
Centreville, MD, 21617

About: I will love and take care of your pets as if they were my own. I love to go out and play with pets I care for. I would dog sit when I was in high school for different families. Those families loved how attentive I was, and as a result they would refer me to their friends. I’m always available for you buddies! You and me both know that your pets are more than pets, theyre family. You don’t want just anyone taking care of family. I do currently work full time, however I have a job that is extremely flexible. I set my own hours, including when I am in my office. This pairs perfectly with animal care and house care because I can come and go as frequently as needed. Due to my open schedule I can be available for any needs your pets may have. I prefer to let the client tell me exactly what they want for their pet. I like to keep your life as simple as possible while giving you peace of mind by following any requests you have. If you need your animal crated, if you want them roaming, whatever is asked you can expect to be done.

Sitter Profile Image: Courtney W.
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Courtney W.
from
$25
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Townsend, DE, 19734

About: Hey, I’m Courtney, a passionate animal lover with hands on experience in veterinary care and a deep commitment to keeping pets happy, safe, and loved. I’m a recent graduate from Delaware State University and I work as a Veterinary Assistant at a local animal hospital in Middletown, DE. Over the years, I’ve cared for dogs of all sizes and personalities from cuddly to high energy. My experience includes everything from administering medications, handing emergencies, senior and puppy care,daily walks, playtime, and providing lots of belly rubs! Whether you’re looking for drop in, dog walking or overnight care, I bring professional compassionate care tailored to your pet’s needs. I treat every dog like family because that’s what they deserve. Let me know how I can help give you peace of mind while you’re away. I’m excited to meet your furry friend. Im working full time as a veterinary assistant, but I’m still available to your pet depending on your needs morning or nights to play with them and give them care. I have an extra crate at home. In clients home I like to establish trust and bonding with pets. Maintain a routine if any for the pet and provide good stimulation.

Sitter Profile Image: Kevin M.
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Kevin M.
from
$15
per walk
30 years of experience
Townsend, DE, 19734

About: I’ve taken care of dogs including raising 5 of my own for over 30 years. Happy to drop in or provide walks as needed. Look forward to hearing from you. I work from home every other week which enables me the flexibility to drop in and take your pup for a walk or feed and let them out. I’ve taken care of dogs including raising 5 of my own for over 30 years. Happy to drop in or provide walks as needed. Let me know how I can help

Sitter Profile Image: Taylor G.
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Taylor G.
from
$20
per walk
5.0 out of 5 stars
49 reviews
2 repeat clients
10 years of experience
Smyrna, DE, 19977

Taylor was great with our dog. She asked questions and took detailed notes. We will definitely be using her services again.

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Devon C.
Sitter Profile Image: Beverly H.
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Beverly H.
from
$30
per walk
5.0 out of 5 stars
13 reviews
1 repeat client
10 years of experience
Church Hill, MD, 21623

Beverly was awesome. We needed someone on short notice and she stepped right in for us. She met the dogs the night before and today she kept us updated on both the walks. Highly recommend her services.

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MIchael C.
Sitter Profile Image: Breanna P.
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Breanna P.
from
$18
per walk
5.0 out of 5 stars
56 reviews
19 repeat clients
16 years of experience
Middletown, DE, 19709

Breanna was perfect. She came through for us last minute and took great care of our boy.

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Dan R.
Sitter Profile Image: Aaron W.
Verified Enhanced Background Check
Aaron W.
from
$25
per walk
25 years of experience
Worton, MD, 21678

About: I have lots of compassion when it comes to animals, and I have years of experience working for cat/dog rescues as well as pet transports, I currently have a four day weekend at my current job and have way too much free time! I also have no problem with early mornings or late nights! I have two small dogs that I take for a couple walks a day, and I Help prepare their food which is home made and all natural. I also have a cat with urinary tract issues so I’m used to keeping their litter boxes spotless.

Sitter Profile Image: Hannah B.
Verified Enhanced Background Check
Hannah B.
from
$20
per walk
5.0 out of 5 stars
1 review
1 repeat client
10 years of experience
Warwick, MD, 21912

About: When I was around 8 I started volunteering at a barn simply because I loved to be around animals. I was constantly walking my neighbors dogs and my own. I now work at a boarding facility where I take care of dogs and cats. I love it and enjoy nothing more than making sure your pets are happy and cared for when you are not able to be there all the time. My friends and neighbors often ask me to watch their pets when they are away. My family currently has 3 rescue dogs, a cat and 3 horses. I look forward to the opportunity of caring for your fur babies!! I am going into my freshman year of community college and love the opportunity to be able to do something that I love in my free time I currently have 3 dogs that get along really well with each other and other dogs. I pay very close attention to how dogs act around each other and their environment to ensure they are safe.

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The median cost per walk for dog walking in Chesterville is $20

Dog parents share their Rover experiences - Chesterville

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5.0 out of 5 stars

Dawn did a great job taking of our dog (7 year old beagle mix). She followed all instructions, took long walks and sent us multiple pictures of our dog each day. This is the first time we have had anyone other than family and friends take care of our Cooper. We are more than satisfied with the experience and will definitely book again.

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Samantha F.
Dog Walking
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  • 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

    Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for dog walking - Chesterville

Select a filter and find qualifying sitters offering dog walking.

Sitters in Chesterville average 3
repeat dog walking clients

FAQs for Dog Walking - Chesterville

Frequently asked questions about Rover

As of August 2026, there are 2,418 sitters on Rover offering Dog Walking across Chesterville. 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 Chesterville. 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 Chesterville.

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 Chesterville. On Rover:

  • 95% of walkers can help with special care needs
  • 98% 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 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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