Pet Sitting Chester

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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Over 57
pet parents in Chester have booked pet sitting

Chester, 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: Brigid S.
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Brigid S.
from
$20
per visit
5.0 out of 5 stars
4 reviews
18 years of experience
Chester, MD, 21619

Very friendly, knowledgeable, competent, reliable. Came to the house for last minute weekend care of our cats. Sent pictures during the weekend. We definitely recommend Brigid.

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zetasean s.
Sitter Profile Image: Bohdanna G.
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Bohdanna G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
79 reviews
28 repeat clients
25 years of experience
Stevensville, MD, 21666

My 2 dogs loved Bo as soon as she walked in the door for our meet & greet. She did 3 drop-ins on 1 day & took wonderful care of our pups. Bo sent updates & pictures of each visit. This is our first time using Rover & Bo is the perfect fit. She is a very caring & professional person who treats your pets & house like hers. Great communication!

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Wanda M.
Sitter Profile Image: Mary L.
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Mary L.
from
$25
per visit
4.9 out of 5 stars
36 reviews
16 repeat clients
30 years of experience
Stevensville, MD, 21666

Mary took wonderful care of my Kitty, Prim. Prim is usually a scaredy-cat and keeps her distance but came right out to Mary for cuddles. Great communication and updates. Will use again. Thank you Mary!

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Jenny H.
Sitter Profile Image: Savannah T.
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Savannah T.
from
$30
per visit
5.0 out of 5 stars
10 reviews
4 repeat clients
1 year of experience
Stevensville, MD, 21666

Savannah was so friendly and helpful. She handled everything how i would have. My boys are pretty emergentic and cuddly- she was able to really help me feel at ease while we were gone. She did a wonderful job and we will be using her again for sure!

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ruthie b.
Sitter Profile Image: Jason & Tracy Y.
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Jason & Tracy Y.
from
$12
per visit
4.9 out of 5 stars
78 reviews
31 repeat clients
10 years of experience
Stevensville, MD, 21666

Jason is very good with our dog, Samson. He loves Jason and responds well on walks with him. Jason is very patient and knows how to handle him well with all of his puppy energy.

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Frank & Teresa R.
Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$40
per visit
4.9 out of 5 stars
21 reviews
6 repeat clients
20 years of experience
Stevensville, MD, 21666

Lena was a calm, caring presence for my senior kitty -- just what he needed. I so appreciated her photos and videos as well. Will definitely use her again!

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Laura T.
Sitter Profile Image: Bryan J.
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Bryan J.
from
$20
per visit
5.0 out of 5 stars
3 reviews
3 repeat clients
20 years of experience
Chester, MD, 21619

Bryan did an excellent job dropping in on our two elderly dogs and my cat 4x a day for three days. I highly recommend him. He followed my instructions with medications for my dogs precisely. Walked and spent time with them all and sent great pictures and reports daily. We are very pleased with Bryan’s outstanding care for our fur babies. I already rebooked with him for future dates.

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Joanna Z.
Sitter Profile Image: Brooke F.
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Brooke F.
from
$25
per visit
5.0 out of 5 stars
77 reviews
17 repeat clients
10 years of experience
Chester, MD, 21619

I needed a last minute sitter just to stop at my house and feed my dog this last weekend (mind you- he’s a German Shephard/Lab- he’s a big boy!) breakfast and take him out to go potty. I have been hesitant to use a kennel, as my dog was severely bit a few months ago. So I turned to Rover- Brooke was luckily able to pick up the job at the last minute and help out! She met with me the day before, we video chatted and she was understanding of Ace’s routine and our home guidelines. She has tons of experience with dogs! I highly recommend Brooke & will be using her again!

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Chrissy L.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$25
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Chester, MD, 21619

Thank you Hannah for this trial run. Taking the time to get to know my boys & their schedules We are looking forward to our vacation now knowing they will be well taken care of while we are gone

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Julie B.
Sitter Profile Image: Rachel R.
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Rachel R.
from
$20
per visit
8 years of experience
Stevensville, MD, 21666

About: I have been caring for cats and dog since I was a freshman in high school and have pet sat for several families! I have taken care of all different breeds from small to big and young to old! Whether it’s just a quick feed, playtime, administering medicine, or overnight care, I will make sure your pet feels loved, safe, comfortable, and cared for! I currently work at a produce stand working about 5 days a week! My schedule however is extremely flexible as I get to choose the days I want off. I also work with other girls my age that pet sit and we are able to leave when needed to provide care! In my home, we have a nice sized backyard where I am able to play catch and I also live in a large neighborhood where I walk everyday and can exercise with your pet! I also have a clean house if your pet is indoors!

Sitter Profile Image: Ryan L.
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Ryan L.
from
$25
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
25 years of experience
Annapolis, MD, 21409

About: I’ve been a lifelong "dog guy" and have spent years caring for the pets of friends, family, and neighbors. As the saying goes, "There are no strangers here; only dog friends you haven't yet met." I’m an expert at making dogs feel loved and secure while their parents are away. I find that exercise and companionship make for happier fur friends. I am a freelancer, which allows me to be very punctual and reliable for morning, mid-day check-ins, or afternoon walks. I understand how hard it is to leave your pet, so I like to send updates and fun photos so you never feel out of the loop. I’m happy to help with: *Standard neighborhood walks/jogs *Drop-in visits for potty breaks and playtime. *Feeding and refreshing water bowls. Attuned to dogs with diet restrictions *Transporting your four-legged loved one to parks (example: Greenbury Point, Quiet Waters Park) *Transporting to the groomer, vet appointments I have great flexibility in the mornings and afternoons. Mon- Friday Morning: 5:00 am - 2:00 pm Evening: 3:30 pm-9:00 pm Saturday-Sunday 5:30 am - 9:00 pm Care in my home: I have a large fenced yard, great for playing catch, if you require morning or afternoon care away from your home. Care at your home, where most pups prefer, I can follow your family's routine: potty breaks, exercise level.

Sitter Profile Image: Emmy S.
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Emmy S.
from
$15
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Stevensville, MD, 21666

Emmy was absolutely wonderful! She took amazing care of our baby while we were away and went above and beyond to stay in touch and make sure he always had what he needed. We highly recommend Emmy and will definitely be using her again. Thank you, Emmy!

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Courtney C.
Sitter Profile Image: Terri H.
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Terri H.
from
$20
per visit
7 years of experience
Stevensville, MD, 21666

About: Hello! My name is Terri but I usually go by T. I have owned both dogs and cats my entire life. Ive worked as a supervisor at 2 boarding and daycare facilities over the course of 4 years until I ultimately moved into veterinary medicine as a technician at a specialty clinic! So I have a lot of experience and am comfortable around all breeds,sizes, ages, and most (stable) medical conditions. I’ve always had a special place in my heart for animals and promise to provide the best care possible to ensure that your fur baby gets all the love he or she deserves. I’ll treat them like my own and you can rest easy knowing your pet is getting all of their necessities and some extra love along the way. I work as a surgical veterinary technician 5 days a week so walking is a side gig for me on my off time but the more time I get to spend around animals the better :) I promise to follow any particular instructions/tips you have for keeping your pups safe and happy! As well as provide some extra love in the process.

Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
30 years of experience
Annapolis, MD, 21409

Tiffany was a real trouper to come visit our 3 month old puppy. She is knowledgeable, organized and loves dogs. Communicates promptly, and is open to changing circumstances. I highly recommend her.

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Shirley C.
Sitter Profile Image: Brianne S.
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Brianne S.
from
$25
per visit
4.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Chester, MD, 21619

About: Before joining Rover I mainly provided my services through word of mouth. I have experience with providing basic medical care for dogs and cats, and training experience including potty training and easing separation anxiety. I have vast experience and knowledge on various breeds and their specific needs, and really just love being able to have the time and availability to be able to provide these services. They say a dog is a man’s best friend, but in my case, a dog has always been a woman’s best friend! I offer dog sitting, walking, training and boarding at my home as well. I am brand new to the app but I do have plenty of references and want to make all owners feel just as comfortable as I want to ensure their pets will feel with me! I currently work a part-time job from my home, so I have a flexible schedule and able to meet any needs your pet has. I am available everyday, all hours mainly, and can accommodate you and your pets schedule! In my home all pets are welcome. I have plenty of walking trails and a back yard for pets that stay at my home. I typically will customize the walks, food, bathing etc depending on the needs of the pet and what works best for them and the owner.

Sitter Profile Image: Julie K.
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Julie K.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Chester, MD, 21619

She was amazing!! Super flexible with our crazy schedule!

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Jenna K.
Sitter Profile Image: Cristina M.
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Cristina M.
from
$30
per visit
5.0 out of 5 stars
9 reviews
25 years of experience
Stevensville, MD, 21666

Cristina is an excellent pet sitter! Our sweet kitty is in end stage cancer and Cristina took such great care of her, ensuring she got her shot and monitored her food/water intake to assure us that all was well while we were away. I would definitely hire Cristina again!

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Sue M.
Sitter Profile Image: Lindsay G.
Verified Enhanced Background Check
Lindsay G.
from
$20
per visit
5.0 out of 5 stars
2 reviews
3 years of experience
Chester, MD, 21619

Lindsay is very friendly and took great care of our pet(s) plus did everything we asked and extra! Thank you so much! We would love to book again soon!

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Ashley R.
Sitter Profile Image: Kate M.
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Kate M.
from
$25
per visit
4.8 out of 5 stars
5 reviews
2 repeat clients
32 years of experience
Chester, MD, 21619

About: I absolutely love animals. I currently have a black lab and I love to just spend time cuddling with her, or going for long walks. If possible, I try to bring her along (assuming they get along at the meet and greet). I’ve noticed that dogs can wear each other out a lot faster than I can, and probably have more fun doing it too. Maddie gets along with everyone and just loves to meet someone new. For your dog, I will treat him/her as my own. I will play with them and take them for walks. I have no problems cleaning up messes, sometimes accidents happen. Let me love and take care of your pet so you don't have to worry about them during the day. Why I love dog sitting I've always been an animal lover. I've had dogs all my life and had two of my own. They truly are the best things that ever happened to me. I’m very active, so I would spend as much time outside as possible with your fur baby. My experience administering medication: I am fine with administering medication, but would like to have the owner show me the correct way of doing it before I start.

Sitter Profile Image: Amanda M.
Verified Enhanced Background Check
Amanda M.
from
$25
per visit
5.0 out of 5 stars
1 review
15 years of experience
Chester, MD, 21619

About: I love playing with dogs and walking them. I've grown up around all types of dogs small and large. I'm very fun and outgoing as well as criminal justice trained ensuring your pets safety. I have taken care of our families dogs as well as watching other family friends pets. I have watched animals with allergies and medication needs. Dogs of all ages are welcome. I will meet any needs of the dog/dogs and ensure to have them back to you safe worn out and happy. I work part time so most of my day is running errands or cleaning the house. If they love car rides they are more than welcome to drive around with me. I will adjust my schedule to meet the needs of the dog or animal. Also absolutely love my kitties. Open to all animal requests just ask! Im a full time optician and part time cook. With plenty of notice I will take off my parttime job to care for your babies. Your pet will be loved as family. Your pet will be able to sleep with me and get full access of my apartment. Toilet bowl lids will always be closed

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

Pet parents share their Rover experiences - Chester

1 / 1
5.0 out of 5 stars

Very friendly, knowledgeable, competent, reliable. Came to the house for last minute weekend care of our cats. Sent pictures during the weekend. We definitely recommend Brigid.

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zetasean s.
Drop-In Visits
5.0 out of 5 stars

We just love savannah. We always know are dogs are loved and played with! We always recommend her to everyone we know! Shes the best. 🐾

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ruthie b.
Drop-In Visits
5.0 out of 5 stars

Allie was great and I'd definitely recommend her! I really appreciated her communication and how much she cared for my kitties.

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Tim
Drop-In Visits
5.0 out of 5 stars

I could tell you guys had good quality time Thanks so much Meanwhile Beans is doing very good & it was not cancer ❤️❤️❤️

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Julie B.
Drop-In Visits
5.0 out of 5 stars

Rebeka couldn’t be nicer and handled our handful of a dog very well. She responds to messages quickly, and I appreciated her reaching out to confirm the day of our scheduled appointment. She is very prompt and has a lot of dog behavioral experience that is helpful. I would not hesitate to use her again!

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Stacey S.
Drop-In Visits
5.0 out of 5 stars

Loved MariAnn. She was prompt, professional, and took excellent care of our three fur babies. I would very much use her services again. Plus I loved the photos she sent.

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Lynn C.
Drop-In Visits
5.0 out of 5 stars

Thank You Jackson, It is such a relief knowing the pets can stay in their own home and are well taken care of.

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Thomas T.
Drop-In Visits
5.0 out of 5 stars

Stacey was so great taking care of our two kitties and watching over our home while we were away. She is just so wonderful and thoughtful and our cats love her! Always keeping us up to date on their daily activities and they got plenty of scratches and love from Stacey while we were away. She’s just the best!!

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Sarah B.
Drop-In Visits
5.0 out of 5 stars

Sydney met with me and Jojo beforehand and then did a drop-in visit with Jojo. Jojo loved her visit. It was nice knowing I can count on Sydney while I am at work and I received a report card, pictures & a video! Thanks so much!

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Cheryl C.
Drop-In Visits
5.0 out of 5 stars

Our dog, Daisy, loved spending the day with Melanie. In fact, she didn’t want to go home at the end of the day. I also appreciated Melanie as a pet sitter.She was always communicative and easy going. Highly recommend!

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Anne S.
Drop-In Visits
5.0 out of 5 stars

Cristina is an excellent pet sitter! Our sweet kitty is in end stage cancer and Cristina took such great care of her, ensuring she got her shot and monitored her food/water intake to assure us that all was well while we were away. I would definitely hire Cristina again!

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Sue M.
Drop-In Visits
5.0 out of 5 stars

Lindsay is very friendly and took great care of our pet(s) plus did everything we asked and extra! Thank you so much! We would love to book again soon!

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Ashley R.
Drop-In Visits
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Popular requests for pet sitting - Chester

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Sitters in Chester average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Chester

Frequently asked questions about Rover

The average cost for Pet Sitting in Chester on Rover is $21.09 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet Sitting 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 Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 5,022 sitters on Rover offering Pet Sitting across Chester. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chester stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 Chester. On Rover:

  • 92% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 95% 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 pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters 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 sitter.

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