Dog Walking Chesterville

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Sitter Profile Image: maranda c.
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maranda c.
from
$20
per walk
5.0 out of 5 stars
• 17 reviews
5 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: Liliana O.
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Liliana O.
from
$25
per walk
5.0 out of 5 stars
• 16 reviews
3 repeat clients
10 years of experience
Chestertown, MD, 21620

“Liliana was great! She was communicative and punctual and was awesome with my dog Ziti! Ziti is high-energy but Liliana did a great job of tiring her out with a nice long walk which was very much appreciated! Would recommend Liliana and would definitely book her again in the future!”

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Margaret E.
Sitter Profile Image: Delaney M.
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Delaney M.
Star Sitter
from
$24
per walk
5.0 out of 5 stars
• 39 reviews
13 repeat clients
9 years of experience
Dover, DE, 19901

“Delaney is great with Nala!! She is very informative about what Nala does on her walk. She seems to care about the pets that she is caring . I am grateful for how she takes. Good care of my girl. Thank you so much, Delaney!! You rock!!”

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Latanya A.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$28
per walk
5.0 out of 5 stars
• 31 reviews
17 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: Josiah S.
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Josiah S.
from
$15
per walk
3.7 out of 5 stars
• 3 reviews
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: 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: Krista K.
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Krista K.
from
$25
per walk
5.0 out of 5 stars
• 15 reviews
4 repeat clients
10 years of experience
Camden, DE, 19934

About: Over the past year, I've had the pleasure of caring for dogs and cats of all ages, from energetic puppies to sweet senior companions. Every pet has their own unique personality and routine, and I take the time to make sure they feel safe, comfortable, and loved while you're away. I have experience administering medications to senior dogs and understand the importance of following care instructions carefully and consistently. Whether it's sticking to feeding schedules, giving medications, going for walks, or simply providing companionship, I treat every pet as if they were my own. When I house sit, I also take great pride in caring for your home. I always aim to leave it cleaner than I found it, so you can come home to happy pets and a tidy, well-cared-for space. My goal is to give you complete peace of mind, knowing both your furry family members and your home are in caring, reliable hands. Caring for animals is already woven into my daily rhythm. I work part-time with flexible hours, giving me plenty of space in my schedule for peaceful walks, playtime, and check-ins with pets. I’m used to creating a balanced routine around my own dog, and bringing that same calm, attentive energy to other pets feels completely natural. I am currently free to sit/walk any day of the week as well as house sit for as long as you need. When caring for pets in a client’s home, I focus on creating a safe, calm, and familiar environment for them. I follow your routines exactly as you outline them — from feeding instructions to walk times to any training cues your dog is used to. I keep doors and gates secured, monitor their body language closely, and make sure they always have fresh water and a comfortable space to relax. Trust is extremely important to me, so I communicate clearly, send updates/photos, and treat your home with the same respect and care I treat your pet.

Sitter Profile Image: Courtney L.
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Courtney L.
from
$40
per walk
5.0 out of 5 stars
• 2 reviews
10 years of experience
Dover, DE, 19904

About: I genuinely love animals. I grew up with two dogs and a cat. I’ve watched over other family dogs and cats for weeks and even months at a time. I work at most 6 hour shifts per day and 4 days per week so I have plenty of free time for play, walking and cuddles. I currently live with one pup who I walk daily before work and we love going on hikes or to the lake on a nice day

Sitter Profile Image: Teresa D.
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Teresa D.
from
$25
per walk
5.0 out of 5 stars
• 100 reviews
36 repeat clients
Frederica, DE, 19946

About: Hello! My name is Teresa! I work full-time on the weekdays but I have weekends free for dog sitting. I have been a dog sitter for a few of my neighbors in the past for fun. Your dog(s) will have a nice house to run around in, we'll take long walks around the neighborhood, going to the Bowers beach, playing in the sand. Since its only me in the house, they will have my undivided attention and love. In the summer, they will be cool, and in the winter, they will be warm by the fireplace. I truly enjoy the company of pets and I look forward to providing you peace of mind and the utmost in care for you and your four legged family members!

Sitter Profile Image: Bridgette M.
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Bridgette M.
from
$20
per walk
8 years of experience
Viola, DE, 19979

About: I’ve been dog sitting, house sitting and dog walking for awhile up to weeks at a time. I enjoy being around all types of dogs small to big. I love getting all the puppy love!! I’m currently babysitting part-time but I can move my schedule around pretty easily and fast. I would like to pursue pet care part time as well! I have a fenced in backyard in a very quiet neighborhood. I have a dog myself. He is very lovable and doesn’t bother anyone. You tell me your feeding schedule and I will go along with it

Sitter Profile Image: Birol M.
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Birol M.
from
$29
per walk
5.0 out of 5 stars
• 108 reviews
27 repeat clients
7 years of experience
Newark, DE, 19711

“Birol is so patient with the doggies owners. 🤓. Birol has such a great energy and delights in being with our doggies. They both took to him instantly. Birol is very thoughtful and conscientious. We lucked out!!”

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Marty M.
Sitter Profile Image: Ella M.
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Ella M.
from
$22
per walk
5.0 out of 5 stars
• 1 review
2 years of experience
Annapolis, MD, 21401

About: As a dedicated dog walker and in-home pet sitter with over two years of experience, I know how important it is to find someone you can truly trust with your pet. I care for every dog (and cat!) as if they were my own — with patience, love, and attention to their unique needs and routines. What You Can Expect: ✅ Safe, fun, and tailored walks ✅ Home visits that follow your pet’s schedule ✅ Clean water, food, meds (if needed), and lots of affection ✅ Daily photo updates and messages so you never have to wonder how things are going ✅ Respect for your home and your pet’s space I’m trained in basic pet first aid and always check collars, leashes, and gates before heading out. Whether it’s a quiet walk or an energy-burning play session, your pet's safety and happiness are always my top priority. Let’s schedule a meet-and-greet! I’d love to learn more about your pet and how I can help make your time away stress-free for both of you. 🐶🐾 Pet care fits naturally into my daily routine because of how flexible and rewarding it is. Since I set my own schedule, I can book pet care clients around my part-time job shifts and study blocks, which helps me stay balanced and productive. Walking dogs gives me a much-needed mental reset from screen time and studying, and it keeps me active throughout the day. It’s also a great way to supplement my income without taking on another traditional job. Most of all, spending time with animals brings me a lot of joy and motivation — it breaks up long study days and reminds me why I love what I do Whether you’re at work or away for a few days, I provide reliable, in-home care that keeps your pets safe, happy, and stress-free in their familiar environment. From daily walks to feeding, playtime, and medication routines, I tailor every visit to your pet’s unique needs. 🔐 Safety & Professionalism Equipped for pet first aid always carrying a kit Detailed home-entry and security protocols Leash and harness checks before every walk Weather-conscious and always alert to potential hazards Respectful of your home, your pets, and your time 📸 Peace of Mind After each visit, you’ll receive a photo and short update so you know how your furry friend is doing — because trust is built on communication

Sitter Profile Image: Chris M.
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Chris M.
Star Sitter
from
$42
per walk
5.0 out of 5 stars
• 67 reviews
21 repeat clients
50 years of experience
Wilmington, DE, 19809

“Chris is wonderful. My dog Archie loves her, which shows how nice she is. She’s been walking Archie.”

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

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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?

  • 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.

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

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog walking - Chesterville

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Sitters in Chesterville average 4
repeat dog walking clients

FAQs for Dog Walking - Chesterville

Frequently asked questions about Rover

As of October 2026, there are 2,436 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 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 Chesterville 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 Chesterville. On Rover:

  • 88% 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 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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