Dog Walking Chesapeake City

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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: Paul C.
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Paul C.
from
$24
per walk
5.0 out of 5 stars
10 reviews
2 repeat clients
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: Kelsie T.
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Kelsie T.
from
$18
per walk
5.0 out of 5 stars
13 reviews
4 repeat clients
15 years of experience
Elkton, MD, 21921

She was great! Will definitely book her again!

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Jenelle C.
Sitter Profile Image: Jenni L.
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Jenni L.
from
$30
per walk
5.0 out of 5 stars
195 reviews
78 repeat clients
15 years of experience
Newark, DE, 19711

Always on time to walk Mulligan. Extremely good with the dog and built a rapport very quickly. Excellent communication and easy to work with. Highly recommend him.

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Karen Q.
Sitter Profile Image: Anneliese C.
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Anneliese C.
from
$23
per walk
5.0 out of 5 stars
21 reviews
7 repeat clients
5 years of experience
Middletown, DE, 19709

Very professional. On time and very canine friendly. Knew exactly how to handle my dog. And he's a big dog (Cane Corso). My dog took a liking to Anneliese instantly. Will definitely use her services again.

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Richard A.
Sitter Profile Image: Mark & Kayleigh B.
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Mark & Kayleigh B.
from
$25
per walk
5.0 out of 5 stars
4 reviews
10 years of experience
Bear, DE, 19701

About: Dogs have always been a big part of my life. I grew up with Border Collies and have also adopted several dogs over the years, so I'm comfortable with everything from high-energy working breeds to laid-back companions. I've also volunteered at several shelters, giving me experience with dogs of different ages, sizes, temperaments, and backgrounds. I work from home (as does my wife) so your pet will be getting consistent, attentive care. To be honest, our dog passed away last fall and we are missing the joy of being dog owners and having dogs around, but we need something a little more flexible for the time being. You are getting two sitters for the price of one and we will care for your dog as if they were our own :) As a former dog parent who has used Rover, my goal is to provide exactly what I was looking for each time I booked a walker/sitter: clear communication, limited hassle, and all of the assurances that you can rest easy and not worry...your doggo is in good hands! I work from home and call my own hours (as does my wife) so as long as we know your dog's routine we will make sure to incorporate it into our own. We have a fenced-in yard and a walking path near our home so walks are never a problem (we love walks). My wife and I both work from home so one of us will always be giving your dog attention/supervision. We have previously owned dogs who were flight risks so we have been conditioned to keep an eye out, keep doors closed, etc. We have a big fenced-in yard and have a little indoor gate/fence that we use in the house if need be to secure a hallway, etc.

Sitter Profile Image: Nancy L.
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Nancy L.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
14 reviews
2 repeat clients
12 years of experience
Newark, DE, 19702

Nancy was fabulous with our dog! She was dependable and respectful. Our dog enjoyed her time with Nancy so much that she was upset when she left. I would gladly book her services again!

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Pat L.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$28
per walk
5.0 out of 5 stars
27 reviews
16 repeat clients
8 years of experience
Townsend, DE, 19734

Luke always has a great time! Thanks again.

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Jeffrey s.
Sitter Profile Image: Amarachi N.
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Amarachi N.
from
$35
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
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: Shirl B.
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Shirl B.
from
$20
per walk
5.0 out of 5 stars
26 reviews
8 repeat clients
12 years of experience
Elkton, MD, 21921

About: Hi everyone! My name's Shirl and I am hoping to make your life a bit easier by taking away the stress of leaving your pup behind while you're away. I have been pet sitting for over 12 years; I used to have dogs come board with me while owners went away, but I've found that most owners prefer their pets to stay in the comfort of their own home. I have years of experience doing overnight pet sitting, but unfortunately my growing family (3 dogs and a cat of my own) no longer allows for me to stay away from home overnight. I am happy to provide multiple daily visits and/or walks! My goal is to keep your pet as comfortable as possible while you're away, by keeping their daily routine as close to "normal" as possible. I've cared for all types of pets including dogs, cats, bunnies, chicks, quail, lizards, fish, etc.! I am an experienced dog handler/ animal lover at heart. I worked at/managed a doggie day care/boarding facility for 4 years, learning from a very experienced trainer who focuses on positive reinforcement techniques ONLY. During my time there, I had opportunities to complete trainings to understand dog behaviors and body language. I have volunteered at BARCS as a dog walker/foster, working primarily with bully breeds. Why I love dog sitting I have been an animal lover my entire life. From playing with salamanders as a kid, to growing up with cats and dogs of all shapes and sizes; I've also had bunnies, fish, frogs, hermit crabs, hamsters, birds...the list goes on! I couldn't imagine a life without animals in it. My experience administering medication Yes. Working at a dog boarding facility for nearly 2 years I have had to give many forms of medications, and my personal pets also take oral medications. I am not trained to give injections. My full time job allows me to work from home majority of the week. That makes it easy for me to swing by for a visit at different times of the day. The latest drop in I can provide is 7pm. I am happy to provide updates as soon as I arrive, during the stay, and as I leave. For dog walks, I prefer not to introduce any dog that I’m handling to another dog passing by. This ensures everyone’s safety.

Sitter Profile Image: Matthew B.
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Matthew B.
from
$25
per walk
5.0 out of 5 stars
56 reviews
17 repeat clients
37 years of experience
Philadelphia, PA, 19104

Matthew is awesome! He’s reliable, energetic, has such a positive outlook, and our greyhound, Guinness, LOVES his walks with him. He treats Guinness like he was one of his own pets. The notifications with pictures, videos, and maps of their walks are very helpful, giving me piece of mind that our best bud is being handled properly in our absence. Since this can be a source of anxiety for me during my “in-office” work days, I feel much better knowing that Matt will come through when we need him. Thanks, Matt. We really appreciate your help last week!

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Jeremy W.
Sitter Profile Image: Lillyanne D.
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Lillyanne D.
from
$20
per walk
5.0 out of 5 stars
10 reviews
5 repeat clients
5 years of experience
Newark, DE, 19702

About: Extremely flexible! I'm experienced in taking care of cats, dogs, turtles, bearded dragons, and fish. I would love to give your furbaby the best care possible! I am a recent graduate from the University of Delaware. My schedule is pretty flexible this summer, I am extremely communicative & love to care for pets. I live with 2 dogs & 2 cats. The cats & dogs are separated. I am very patient with animals! I am also extremely diligent with their care such as cleaning food/water bowls, scooping poop, changing pee pads, following feeding/medication schedule, and playing with animals.

Sitter Profile Image: Reid C.
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Reid C.
from
$62
per walk
5.0 out of 5 stars
69 reviews
18 repeat clients
24 years of experience
Glasgow, DE, 19702

Reid is the best dog caregiver!

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Marianne S.
Sitter Profile Image: Busara C.
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Busara C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
89 reviews
14 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: Christine S.
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Christine S.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
29 reviews
16 repeat clients
25 years of experience
Elkton, MD, 21921

Christine does a phenomenal job caring for our puppy while we are at work. She responds immediately, takes a bunch of pics for us, and always ensures he is comfortable before leaving. Christine always makes sure to meet our specific needs and is very attentive with Arlo. We are so thankful to have such a reliable and kind person to assist us when needed.

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Kourtney R.
Sitter Profile Image: Miabella M.
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Miabella M.
from
$20
per walk
5.0 out of 5 stars
3 reviews
8 years of experience
Wilmington, DE, 19808

About: I’ve cared for pets since age 11, and I truly enjoy giving them the love, attention, and gentle care they need and deserve every day. Pet care fits easily into my daily life because I’m in school, working part-time, and have a flexible schedule that allows me to help whenever needed. I don’t provide in-home boarding, but I always respect and carefully follow each owner’s instructions to ensure pets feel comfortable, safe, and well cared for.

Sitter Profile Image: Lauryn F.
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Lauryn F.
from
$20
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
8 years of experience
Newark, DE, 19711

About: I have done pet sitting for many years, I have worked with multiple different types of animals many times. I love animals, can handle stressful situations, and know how to make responsable decisions regarding your home and beloved animals. I also will communicate effectively and be timely in my care of your pet. I work a job that has a flexible schedule, I do not have any prior commitments on weekends and any pet sitting jobs I book will become top priority. Pets should be treated with just as much respect as any person. Introducing yourself, acting calm and kindly, and also reading body cues and signs to make sure they remain comfortable at all times.

Sitter Profile Image: Emmanuella L.
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Emmanuella L.
from
$25
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
21 years of experience
Newark, DE, 19711

About: I’ve been trusted to watch and play with many family friends pets over the past and have grown up with pets for my entire life. I love animals and would love to spend my college break caring for some! I am currently working part-time so have plenty of time to walk/watch pets and am very amenable with my schedule. Open to working around the owners lifestyle. I carefully listen to instructions and rules set forth by the pet owner and ensure that the animals are safe and well cared for while I am with them!

Sitter Profile Image: Makenzi G.
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Makenzi G.
from
$10
per walk
5.0 out of 5 stars
7 reviews
1 repeat client
5 years of experience
Belcamp, MD, 21017

About: Hi! My name is MaKenzi and I have had pets as long as I can remember, I grew up with two pitbulls rescues, two smaller dogs, and an older cat that I assumed most of the care for as both parents worked full time jobs. Taking care of multiple animals at one time requires a lot of energy and the ability to organize the things they need well but I learned very quickly! Since I have lived on my own I have helped friends and coworkers with taking care of their beloved fur babies while they’re on vacation or just need an extra hand with their pets. In the last year I have rescued my own kitten and I have absolutely spoiled her with all of the patience, love, affection, and extra care that her heart could desire.

Sitter Profile Image: Breanna P.
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Breanna P.
from
$18
per walk
5.0 out of 5 stars
59 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: Lindsey C.
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Lindsey C.
from
$25
per walk
5.0 out of 5 stars
25 reviews
10 repeat clients
8 years of experience
New castle l, DE, 19720

Lindsey was kind, patient and very informative. In under an hour she was geeing out Nova to follow commands.

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clarice m.
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The median cost per walk for dog walking in Chesapeake City is $20

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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
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Popular requests for dog walking - Chesapeake City

Select a filter and find qualifying sitters offering dog walking.

Sitters in Chesapeake City average 4
repeat dog walking clients

FAQs for Dog Walking - Chesapeake City

Frequently asked questions about Rover

The average cost for Dog Walking in Chesapeake City on Rover is $19.98 per walk (as of September 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 September 2026, there are 1,793 sitters on Rover offering Dog Walking across Chesapeake City. 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 Chesapeake City. 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 Chesapeake City.

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 Chesapeake City. On Rover:

  • 96% of walkers can help with special care needs
  • 94% 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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