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 38
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: Bryan J.
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Bryan J.
from
$22
per visit
5.0 out of 5 stars
• 9 reviews
8 repeat clients
20 years of experience
Chester, MD, 21619

“My dogs loved him almost immediately (even my nervous rescue). He has a very quick response rate. I will absolutely plan on booking him again.”

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Frances C.
Sitter Profile Image: Ryan L.
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Ryan L.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
• 19 reviews
7 repeat clients
25 years of experience
Annapolis, MD, 21409

“Ryan is awesome! He took such great care of our dog while we were away. I could relax on vacation knowing how well cared for Napoleon was in Ryan’s care!”

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

“Bo did an exceptional job caring for our kitties. She went above and beyond, providing informative check-ins and plenty of pictures during each visit. Her attention to our communications and responsiveness were greatly appreciated. I will definitely rely on Bo for future trips away from home and recommend her to anyone in need of pet sitting.”

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Madison 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
32 repeat clients
10 years of experience
Stevensville, MD, 21666

“Jason and Tracy are awesome! Very thorough and follow your instructions exactly as you like….and my three pups love them after only 2 visits!! I highly recommend them!”

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Wendy W.
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: Jacqueline G.
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Jacqueline G.
from
$20
per visit
1 year of experience
Chester, MD, 21619

About: What sets me apart from other sitters is trustworthiness, reliability, punctuality, and care. I care for others' animals just as I would my own! With love, attention, and energy. I’m typically available from Thursdays - Sundays. Please reach out to confirm 24 hours in advance so I can make sure my schedule aligns with yours. I can adhere to any guidelines you set for me while in your home. I am a trustworthy and respectful sitter who will take loving care of your furry family members like they're my own!

Sitter Profile Image: Heather B.
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Heather B.
from
$25
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
30 years of experience
Grasonville, MD, 21638

“Heather was fantastic Lola seems happy and ate most of her food which is unusual when she's alone so she must have been to have Heather come by and thanks for all the pictures”

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Andrew F.
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: Summer B.
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Summer B.
from
$30
per visit
5.0 out of 5 stars
• 2 reviews
20 years of experience
Wye Mills, MD, 21679

“Excellent and thorough! Clearly loves dogs and cats. She was on time and did everything I listed for my pets. The Rover site was easy to use and it gave me quick access to pick Summer as our sitter. Will definitely have her back!”

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Mary Ann W.
Sitter Profile Image: Sean K.
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Sean K.
from
$30
per visit
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
Stevensville, MD, 21666

About: I've always been great with animals, able to read them and good at figuring out what they need. I volunteered at Animal Welfare League of Queen Anne's County for several years starting in High School. I've worked closely with large animals with behavioral problems, so I'm down the handle whatever quirks your pet has. My schedule is very flexible, and I can usually provide services as needed when given prior notice. Anytime of day as well, within reason ofc. I'm very adept at reading animals behavior and figuring out when they need attention, when they need space, and good at gaining an animals' trust.

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: alison r.
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alison r.
from
$20
per visit
10 years of experience
Easton, MD, 21601

About: I’ve taken care of dogs and cats my whole life and now I frequently walk, cat/dog sit, and board occasionally in my home. I thoroughly enjoy meeting new furry friends! Im currently working full time but have availability all throughout the day variating some days. For the most part afternoon times are best for the week I care for clients pets exactly how the wish for me to. I never want to impose my own beliefs on an animal that is not mine.

Sitter Profile Image: Marley W.
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Marley W.
from
$30
per visit
5 years of experience
Grasonville, MD, 21638

About: I’ve taken care of my own dogs since I was 8. I had a medium sized low energy dog and now I have a high energy bigger dog so I have a good range of care. I’ve always been the one neighbors have reached out to to take care of their dogs Currently I am unemployed so I am pretty openly available! It really just depends on your dogs needs and how I can best provide for them! I am really good with handling dogs and getting them to listen. I’m super athletic so I’ll love taking your dogs on walks and playing! Super openly available for all there needs.

Sitter Profile Image: Imani W.
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Imani W.
from
$14
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
20 years of experience
Easton, MD, 21601

About: I’ve taken care of dogs since I was 8 my family and friends always ask me to take care of walking ,feeding , and administrating medicine . I work at the Easton Elementary i usually get off anywhere between 3:55-4pm so I can do check ins and or walks Monday through Friday after I get off from work on the weekends I have a very flexible schedule so I can do anytime I had 2 dogs they passed away this year due to older age couple of months ago but I have a backyard with a closed off fence top to bottom so your pets will be very safe and have a good yard to run around and stretch

Sitter Profile Image: Michael P.
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Michael P.
from
$35
per visit
5.0 out of 5 stars
• 76 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: Shacja S.
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Shacja S.
from
$25
per visit
5.0 out of 5 stars
• 9 reviews
3 repeat clients
45 years of experience
Ridgely, MD, 21660

About: Active Dog Loving Grandparents We enjoyed the pleasure of having pets our entire lives, they have brought us a sense of peace and joy and best of all unconditional love. Our best friends have been Boston Terrier’s, German Sheppard’s, American Bulldogs and Boxers. They are all unique in their personalities but all love to be loved, just like us. We are retired so one of us are at home all the time. We live on a great fence property with an awesome nieghborhood that we love to take walks around multiple times a day (weather permitting.) The dogs usually have a grand time taking a run around the property and playing. Should it be too warm of course they enjoy the air conditioning ? Now that our children are grown and married with children/dogs we occasionally keep their Boxer brother (Duke) and sister (Honey) and our grandchildren too. You can feel safe leaving your pets in our care. We will look after them and love them like our own! In fact, they may not want to leave as our grand-dogs do? Can provide a bath prior to your return if you would like. Look forward to meeting you and your baby soon. Grandma J

Sitter Profile Image: Laurie H.
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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.

Sitter Profile Image: Jordan B.
Verified Enhanced Background Check
Jordan B.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
• 12 reviews
3 repeat clients
3 years of experience
Bowie, MD, 20721

“Jordan is so amazing with YODA I am so thankful for his flexibility and kindness”

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Alexis S.
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: Shaniah H.
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Shaniah H.
from
$20
per visit
15 years of experience
Glen Burnie, MD, 21060

About: Dogs have always been part of our family, and I have over 15 years of hands-on experience caring for dogs of all ages, sizes, and personalities. As a family with three friendly dogs, we understand how important it is to know your pet is safe, comfortable, and loved while you're away. We provide a clean, structured, and supervised home where dogs receive plenty of attention, playtime, exercise, potty breaks, and affection throughout the day. We are experienced with puppies, senior dogs, administering oral medications, maintaining feeding schedules, crate-trained dogs, and multi-dog households. Every dog is treated like one of our own. You'll receive regular photo and video updates so you can relax knowing your pet is happy and well cared for. Our goal is to create an stress-free, loving environment where every dog feels at home. My family and I have a flexible schedule that allows us to provide consistent care and supervision throughout the day. Because we work from home part of the week, there is almost always someone available to monitor, play with, and care for your dog. We maintain regular feeding schedules, frequent potty breaks, daily exercise, enrichment activities, and plenty of affection. We offer flexible drop-off and pick-up times whenever possible and work hard to accommodate each family's needs. Your dog's safety, comfort, and happiness are our top priorities. We have a clean, smoke-free home with a dedicated space designed specifically for boarding dogs, giving them plenty of room to relax, play, and feel comfortable. We have three friendly, well-socialized dogs and always introduce pets carefully to ensure everyone gets along. We closely supervise all interactions and can separate dogs whenever needed for meals, rest, or individual care. We follow each owner's feeding schedule, medication instructions, exercise routine, and any special requests. We welcome crate-trained dogs and can accommodate dogs who need extra attention, senior care, or a quieter environment. You'll also receive daily photo and video updates so you can enjoy peace of mind while you're away.

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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

What a great experience. This was my forst time using Rover and Anna made it a great experience. She was communicative and great with my babies. Thank you so much Anna, will definitely use you again and again.

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Lissi A.
Drop-In Visits
5.0 out of 5 stars

She was very communicative. She's definitely a dog-enthusiast at heart, my pack loved her and we will be using her again for sure.

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

Taylor was great with our cats, she even looked in and took care of our bunnies and fish! We could relax on vacation knowing they were in good care! She was reliable and always communicated with us! Thank you so much!!

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Ashley R.
Drop-In Visits
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

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
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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.

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    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

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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 Pet Sitting - Chester

Frequently asked questions about Rover

The average cost of Pet Sitting in Chester is $21 per visit as of November 2026. Most bookings cost between $20 and $26 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 5,070 sitters on Rover offering Pet Sitting across Chester. 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 Chester. On Rover:

  • 86% of sitters can help with special care needs
  • 92% 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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