Pet Sitting Chesterville

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Chesterville, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Dawn D.
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Dawn D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 17 reviews
5 repeat clients
12 years of experience
Chestertown, MD, 21620

“Dawn was fabulous -- both with Athena and with the situation; she came and sat with our dog Athena while there was a wedding going on outside and it was an utter madhouse and she was kind and soothing with both the canine and dog customers. Do not hesitate to book with Dawn. She is knowledgeable and flexible.”

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Marsh R.
Sitter Profile Image: Aaron W.
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Aaron W.
from
$19
per visit
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: maranda c.
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maranda c.
from
$22
per visit
5.0 out of 5 stars
• 17 reviews
6 repeat clients
10 years of experience
Church Hill, MD, 21623

“Fantastic job with taking care of our pets. She took some of the best pictures and kept us thoroughly updated. We would happily use her again.”

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Justin A.
Sitter Profile Image: Ashley C.
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Ashley C.
from
$25
per visit
5.0 out of 5 stars
• 14 reviews
2 repeat clients
10 years of experience
Centreville, MD, 21617

About: I’ve been dog walking and sitting for neighbors since I was 12 years old. I’ve dog sat multiple types of dogs. I’ve done dog walking, check-in & potty break visits, and I’ve stayed at a clients home for long periods of time (5+ days) to be with their pups. I’ve also been tasked with administering insulin shots to dogs before. And I have a lot of experience with dogs that have anxiety, whether with new people, thunderstorms, or anything else, as I have one myself and a long remaining client of mine does as well. I’ve always loved dogs, having grown up having 2 smaller dogs myself. I am hoping to do pet sitting as a new permanent business, so I will have nothing but time to look after your pets! I will schedule out days and time periods based on client necessity and to provide the optimal care for your pets. Because I have two dogs myself, one of which has severe people and other animal anxiety, which for the safety of your pets and mine means I am unable to bring any pets into my home as of current. However, I’ve stayed at the homes of clients before to be with their pups while they’re away. I feed them every morning and night or make sure the food bowl is full depending on how the client feeds their dogs. I give them any medicine or joint tablets that they need to be well. I let them out multiple times a day whenever they need it. And I try to play with and pet them as much as I can while I’m there so they don’t miss their humans too much. I will even take them on a walk if allowed.

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

“Cameryn is the best pet sitter! She truly loves animals and kept us updated on their care while we were away. We would definitely hire her again!”

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Christina L.
Sitter Profile Image: Ann B.
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Ann B.
from
$25
per visit
10 years of experience
Middletown, DE, 19709

About: I’ve been a devoted dog owner for 10 years, and I’m passionate about both dogs and staying active. As a schoolteacher, I’m excited to continue doing what I love while earning extra income to help pay off my student loans and purchase supplies for my classroom. I can walk dogs Monday through Friday after 3:30 pm. If you’re running late and need someone to help out in a pinch, I'm happy to assist. I’m available on Saturday and Sunday to walk your furry friend three times a day, or more if needed. Our dog is incredibly spoiled and loved. Whenever I come home, she brings me her ball, and we play fetch before anything else. She is groomed monthly, walked several times daily, and receives constant attention. When we have salmon, we cook her a plain fillet, which she loves.

Sitter Profile Image: Crystal D.
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Crystal D.
from
$25
per visit
5.0 out of 5 stars
• 11 reviews
5 repeat clients
17 years of experience
Ridgely, MD, 21660

“Crystal was a great sitter. We have 4 different breeds of dogs, (including a puppy and a senior) and she was able to meet all of their individual needs. She was on time and communicated regularly. I felt very comfortable leaving the dogs in her care.”

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Pamela A.
Sitter Profile Image: Josiah S.
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Josiah S.
from
$10
per visit
3.7 out of 5 stars
• 3 reviews
12 years of experience
Centreville, MD, 21617

“Josiah was wonderful! We will be requesting him again!!😊😊”

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Alayne K.
Sitter Profile Image: Samantha C.
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Samantha C.
from
$20
per visit
25 years of experience
Smyrna, DE, 19977

About: Ive had several dogs all sizes, breeds and temperaments and I understand that different dogs need different types of care and attention. I was on Rover a couple yrs ago and I loved working with the bigger dogs! I’ve also worked with and around horses my whole life! I Currently work for The Little Farm daily mainly feeding the animals and working with the horses. My schedule is usually mon-sat depending.. same with the time. I can accommodate as needed! Message me and I can definitely give more info! I’m not able to board due to housing but I can definitely do drop ins and walking! I am available mon-Friday and can talk more about weekends!

Sitter Profile Image: Jen P.
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Jen P.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
• 80 reviews
22 repeat clients
25 years of experience
Middletown, DE, 19709

“Jen is absolutely the BEST petsitter you will ever experience. My cat is very high maintenance with her attitude and her massive hair (forest cat). Upon my arrival home kitty was calm, very content , and had an extensive grooming! My home was exceptionally clean with the removal of litter and cat food cans. Jen met me before the sitting dates and she was extremely knowledgeable . She has tons of common sense--- You will not need to give her pages of instruction. She GETS IT ! In addition, my plants were watered during this 94 degree weather , mail was placed neatly inside, and trash cans were taken to the curb . Photos are sent to you at each visit. Love Jen to take care of my cat.”

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Jane E.
Sitter Profile Image: Lillian S.
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Lillian S.
from
$30
per visit
4.9 out of 5 stars
• 40 reviews
19 repeat clients
25 years of experience
Elkton, MD, 21921

“Lillian was awesome looking after our old cat. I told her our cat was old and small and would probably hide for all the visits. But she just loved Lillian! Came out each time, sat in her lap and got lots of ear rubs. Litter and food areas were cleaned well also. Thanks!”

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Andrew B.
Sitter Profile Image: Steven H.
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Steven H.
from
$25
per visit
3 years of experience
Grasonville, MD, 21638

About: I have hands-on experience caring for my own dogs, Koda and Eddie. Koda is a Cane Corso puppy, which has helped me learn the importance of patience, consistency, positive reinforcement, and proper exercise. I make sure my pups receive plenty of love, attention, playtime, and daily care while keeping their safety and comfort a priority. I understand that every dog has a unique personality and needs, and I would treat every pet in my care like family! 🐶❤️ Pet care is something I enjoy and make time for in my daily schedule. I strive to be flexible, dependable, and attentive to each pet’s needs, ensuring they receive plenty of exercise, attention, and care. I communicate with pet parents to coordinate schedules and make sure every pup gets the time, love, and attention they deserve! 🐾 I prioritize safety, patience, and trust when caring for every pet. I make sure each animal feels comfortable, loved, and secure while following the owner’s instructions and respecting each pet’s unique needs. I believe in keeping open communication with pet parents, providing regular updates, and creating a safe, welcoming environment where both pets and their owners can feel confident and at ease. My goal is to treat every pet like family! 🐾❤️

Sitter Profile Image: Briana B.
Verified Background Check
Briana B.
from
$35
per visit
4.9 out of 5 stars
• 18 reviews
6 repeat clients
12 years of experience
Newark, DE, 19702

“I recently had the pleasure of working with Briana, and I couldn't be happier with the experience! From our first interaction, it was clear that she had a genuine love for animals and a deep understanding of dog care. Briana took the time to get to know my dogs' personalities, habits, and specific needs, which put me at ease right away. During the time I was away, she provided regular updates and adorable photos, which reassured me that my pups were in great hands. Thank you Briana”

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

“Birol is the best- we are so appreciative for how thorough and thoughtful he is. 1000/10 recommend”

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Maura G.
Sitter Profile Image: Courtney L.
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Courtney L.
from
$40
per visit
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: Lauryn F.
Verified Enhanced Background Check
Lauryn F.
from
$25
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
8 years of experience
Newark, DE, 19711

“Great communication, responsive, excellent job.”

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Nicole D.
Sitter Profile Image: Jamiah B.
Verified Background Check
Jamiah B.
from
$20
per visit
5.0 out of 5 stars
• 54 reviews
25 repeat clients
20 years of experience
Wilmington, DE, 19805

“Jamiah dropped by my apartment daily to take care of my two cats while I was on vacation, including feeding them and cleaning the litter boxes. Since cats get stressed in new environments, I really did not want to board them, so the house visits worked out great! Jamiah is super friendly and has cats of her own, so I knew I wouldn't have to worry leaving them. She took great care of the cats and sent lots of photos. I would definitely recommend Jamiah for pet-sitting!”

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Kim T.
Sitter Profile Image: Michael P.
Verified Enhanced Background Check
Michael P.
from
$35
per visit
5.0 out of 5 stars
• 75 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

“Our cats felt very comfortable with Michael, and so did we! He's reliable, kind, and respectful of animals, and also very intuitive with them. Their personalities are very different, but he gave Bagheera plenty of active play and made friends with the very shy Laska. We highly recommend Michael and will use him again. Great Rover cards, by the way!”

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Margaret C.
Sitter Profile Image: Heather B.
Verified Enhanced Background Check
Heather B.
from
$35
per visit
5.0 out of 5 stars
• 38 reviews
14 repeat clients
18 years of experience
Wilmington, DE, 19803

“Thanks Heather for taking such great care of Moxie and Stella last night!”

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Stefanie B.
Sitter Profile Image: Laurie H.
Verified Enhanced Background Check
Laurie H.
from
$30
per visit
45 years of experience
Annapolis, MD, 21401

About: I truly adore cats and their unique personalities. I'm a retired empty nester, who is flexible, attentive, patient, affectionate, and I believe great cat care includes a fresh, spotless litter box every day. Your cat will get plenty of love, attention, and a comfortable environment giving you a peace of mind while you're away. Being retired gives me a flexible schedule and plenty of time to devote to your pets, providing attentive, dependable care without rushing or juggling another job. Whether in my home or yours, I follow each pet's normal routine, providing plenty of love, attention, exercise, fresh water, clean spaces, play time and personalized care.

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The median cost per visit for pet sitting in Chesterville is $20

Pet parents share their Rover experiences - Chesterville

1 / 1
5.0 out of 5 stars

Patient and great communication throughout our guy was taken care of and would definitely use again!

Profile image
Ryan W.
Drop-In Visits
5.0 out of 5 stars

Dawn was fabulous -- both with Athena and with the situation; she came and sat with our dog Athena while there was a wedding going on outside and it was an utter madhouse and she was kind and soothing with both the canine and dog customers. Do not hesitate to book with Dawn. She is knowledgeable and flexible.

Profile image
Marsh R.
Drop-In Visits
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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.

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  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 pet sitting - Chesterville

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Chesterville average 6
repeat pet sitting clients

FAQs for Pet Sitting - Chesterville

Frequently asked questions about Rover

As of November 2026, there are 2,545 sitters on Rover offering Pet Sitting across Chesterville. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter 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.

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.

Yes, you can find sitters who have experience with handling special pet needs in Chesterville. On Rover:

  • 88% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 94% 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 sitter 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 sitter 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 sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, 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 sitter.

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