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 263
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: Abby M.
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Abby M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
293 reviews
106 repeat clients
14 years of experience
Chester, VA, 23831

Abby was great! She responded to my last minute request. She was very respectful and polite. Sir loved her and she sent plenty of pictures during her visit. I will definitely be using her again!

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Delrita B.
Sitter Profile Image: Annabella C.
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Annabella C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
23 reviews
9 repeat clients
4 years of experience
North Chesterfield, VA, 23237

Annabella was able to help with Elvis very last minute and she was so great and patient with him. Would absolutely recommend her, she was fabulous !

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Ruby V.
Sitter Profile Image: Indiana M.
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Indiana M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
38 reviews
13 repeat clients
15 years of experience
Chester, VA, 23831

Indiana was phenomenal to work with. Took excellent care of our cats, was super respectful of our home and helped take care of a few things here and there in our house. Was also very communicative and let us know what was happening with our pets. 10/10 she’ll be our go to pet sitter whenever we are in need and she should be your go to as well!

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Azmi K.
Sitter Profile Image: Amanda B.
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Amanda B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
28 reviews
7 repeat clients
20 years of experience
Chester, VA, 23831

Well, well, didn’t we just find the perfect lover of dogs, even the crazy and energetic ones like ours? Amanda was perfect with our crew, sending pictures and updates and making sure they always had fun and got snuggles while we were away. I think the dogs are ready for us to head out of town again so that Miss Amanda will come back to play! (And we will be soon, boys!)

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Traci L.
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
214 reviews
60 repeat clients
10 years of experience
Chester, VA, 23831

Allison did a great job with my two cats while my family and I were out of town. During our trip, we had a false alarm trip from our alarm system. Even though the police checked and cleared the scene, I asked if she'd check the window where the alarm originated on her next visit. She has no problem checking it and also took pictures per my request. She responded to all my messages quickly and sent fun pics of my girls. Overall great experience, thanks Allison!

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Michelle G.
Sitter Profile Image: Phyllis N.
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Phyllis N.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
110 reviews
47 repeat clients
50 years of experience
North Chesterfield, VA, 23237

Phyllis did an exceptional job! She was on time and took phenomenal pictures of my cat Mable! If your looking for someone who is trustworthy and cares for your pets as much as you do, she's the lady!!!!! 10/10

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eric o.
Sitter Profile Image: Crystal C.
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Crystal C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
299 reviews
107 repeat clients
15 years of experience
South Chesterfield, VA, 23834

Crystal did a fantastic job with our cat while we were out of town. I loved the pictures, descriptions of the visits, and reassurance that Artemis was doing perfectly fine. We won't hesitate to use her again. Thanks Crystal!

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Michelle G.
Sitter Profile Image: Lisa C.
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Lisa C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
71 reviews
21 repeat clients
40 years of experience
North chesterfield, VA, 23237

If you’re looking for someone reliable, thorough, and trustworthy it is Lisa! She has been so accommodating and helpful with our dogs, especially when we made last minute arrangements to our schedule.

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Mallory N.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
53 reviews
14 repeat clients
15 years of experience
Chester, VA, 23831

Sabrina took amazing care of our cats while we were away and sent plenty of photos. We wouldn’t hesitate to trust her with them again on our next trip!

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Casey B.
Sitter Profile Image: Samantha B.
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Samantha B.
from
$35
per visit
5.0 out of 5 stars
31 reviews
17 repeat clients
30 years of experience
Chester, VA, 23831

Samantha was great with my 2 pups! They seemed happy when I got home from work-no complaints from them. Received pictures throughout the drop in visit, which was nice. Definitely will book again

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Evelin V.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$20
per visit
5.0 out of 5 stars
41 reviews
21 repeat clients
18 years of experience
Chester, VA, 23831

Jessica has dropped by on my pupsters on two separate occasions, and I would trust her anytime I need some help. She always provides adorable updates and is communicative. The pups have a great time with her. I will book Jessica everytime if she's available!

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Erin B.
Sitter Profile Image: Jynette V.
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Jynette V.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
30 years of experience
Chesterfield, VA, 23832

About: I've raised dogs my whole life. Everything from cocker spaniels to a golden retriever. I recently upped the difficulty by training our puppy to be a service animal. Happy to play, cuddle, or just let them have a quiet place to settle. I have no problems taking care of your baby. While I'm newer to cats my partner has fostered kittens to elderly cats and is passing on their knowledge. I am currently full time at home so I have a very open schedule to help your fur baby with all those difficult times when you can't be with them. Your home and your fur baby will be treated with complete respect. I understand that I am being trusted with one of your most precious possessions.

Sitter Profile Image: Alyssa H.
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Alyssa H.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
6 years of experience
Richmond, VA, 23235

She was very thorough and communicated each step of the way. I will definitely use her services in the future.

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Kristie M.
Sitter Profile Image: Amanda W.
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Amanda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
59 reviews
17 repeat clients
15 years of experience
Chesterfield, VA, 23832

Amanda is great with our shy tortie, Kallie! She goes above and beyond with extra pets and attention. We always come home to a happy cat and a clean home. I would definitely recommend her!

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Jackie N.
Sitter Profile Image: Grace L.
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Grace L.
from
$20
per visit
5.0 out of 5 stars
40 reviews
14 repeat clients
17 years of experience
South Chesterfield, VA, 23834

Grace sent us lovely updates and pictures of our cats each day which made being away much easier. The cats were well played with and barely seemed to notice when we returned 🤣.

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Shelley. R.
Sitter Profile Image: Alecia B.
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Alecia B.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
60 reviews
20 repeat clients
20 years of experience
Chester, VA, 23836

Alecia was very prompt with her visits and she was wonderful with my fur babies. I appreciate it her patience and knowledge of dealing with all types of dogs.

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Dwayne H.
Sitter Profile Image: Lilliana C.
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Lilliana C.
from
$20
per visit
4.8 out of 5 stars
9 reviews
5 repeat clients
10 years of experience
Chester, VA, 23836

Lilliana was excellent and extremely professional. She was on time and went the extra mile to make sure our pets were taken care of. I will definitely be using her services again.

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Nykita J.
Sitter Profile Image: Journei F.
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Journei F.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
7 years of experience
Richmond, VA, 23234

About: I’ve been taking care of pets for most of my life. My family and friends have always counted on me to care for our/their pets when needed. I have walked, bathed, fed, snuggled and played with them! I am a full time worker, five days a week, nine hours a day from 9AM to 6PM. And I also have a part-time job that I do on the weekends, but I am still open to any service I could possibly provide for you and your pet! I receive my part-time job schedule weekly schedule every Saturday, so communication is key. I will care for your pets in your home by providing them the care that they need, walks, runs, snuggles, playtime, you name it! If there is anything specific you want me to know or abide by please let me know and I will make sure you and your pet are left satisfied :)

Sitter Profile Image: Joanette C.
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Joanette C.
from
$40
per visit
4.9 out of 5 stars
42 reviews
18 repeat clients
9 years of experience
A chesterfield, VA, 23834

Thank you so much. She did very good with the cats, and they are not the easiest. Always showed up and made sure they were happy and took lots of pics 🙂

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erin u.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$14
per visit
5.0 out of 5 stars
2 reviews
5 years of experience
Richmond, VA, 23234

About: Animals have always been a big part of my life. I have over 5 years of experience caring for dogs of all breeds, sizes, and personalities, including my own pets and my professional experience as a kennel attendant at a pet daycare. I’m experienced with walks, feeding routines, baths, medication, and providing care for pets with different needs and temperaments. I understand that every pet has their own personality and routine, so I take the time to make sure they feel safe, comfortable, and cared for. My goal is to give your pet the same attention, patience, and love I would give my own. I have a flexible schedule that allows me to give pets the time and attention they deserve. I plan my days around making sure each pet gets proper care, playtime, walks, and check-ins without feeling rushed. I treat every pet like they’re my own. I focus on keeping them safe, comfortable, and following their normal routine so they feel relaxed while their owner is away. I pay attention to their behavior, needs, and any instructions provided to make sure they receive the best care possible.

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

Pet parents share their Rover experiences - Chester

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5.0 out of 5 stars

Amanda was absolutely amazing! My Ollie loved her immediately which was so comforting being that this was my first time leaving him alone with someone other than a family member. Amanda was prompt, communicative, and even did more than she was expected to, which made it very clear she loved my pup and it brought me so much comfort being away. 10/10 recommend reaching out to her for all your pet care needs.

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Amanda L.
Drop-In Visits
5.0 out of 5 stars

Phyllis was amazing! She took perfect care of our cat, sent thorough updates, and kept the house in order while we were away. We will absolutely use her in the future whenever we can!

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

Sam is AMAZING!!!!!! I cannot say enough about how lucky we were to find Sam. Unexpectedly, just a few days before a lengthy trip, one of our senior pups suffered a seizure in the middle of the night. We couldn't cancel our trip, but we found ourselves with increased anxiety about leaving the dogs and unable to ask our usual housesitter to potentially administer his new emergency medications. We were immediately drawn to Sam's experience as an ER vet tech, but meeting her surpassed even our wildest hopes: she has such a deep wealth of experience in caring for animals and a real passion for ensuring animals live their best, most comfortable lives. As part of her daily visits, Sam did wellness checks on the dogs and sent us detailed, reassuring updates about how well our dog was adjusting to his new medication. Recognizing their limited mobility, she spent her visits loving on them and doing gentle stretches to help with their joints. We returned to healthy, happy pups, and the peace of mind we were able to find on the trip, especially knowing our medically complex dog was in such great hands, was invaluable. We will happily work with Sam again and cannot recommend her to others more highly!

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Jenna G.
Drop-In Visits
5.0 out of 5 stars

Abby is amazing with our sweet old girl. Sadie doesn’t like many people but fell in love with Abby. Thank you again

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

Sabrina took great care of our 3 boys. I'm glad my boys got to stay cozy in our home while we were on vacation. Sabrina sent us pictures of each and they warmed up and were playful even excited Sabrina was there. I highly recommend Sabrina she took great care of our fur babies and will book in the future!

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Judith E.
Drop-In Visits
5.0 out of 5 stars

Annabella was an amazing sitter for our dog, Ash! She communicated about each visit and sent us some pics of our sweet boy. She was on time each day and even cleaned his bowls and lick mats for us so we came back home and could get back into our routine easily.

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Katie W.
Drop-In Visits
5.0 out of 5 stars

Rebecca was amazing - we last minute needed a sitter and she was able to help. She would send us updates when she would drop in and we loved the pictures she sent us as well. She did a great job and I already rebooked her!

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

My cats are very shy and it looks like they didn’t end up interacting with Indiana, but she sent me pictures of them hiding every day :)

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

Tiffany was a joy to work with. Great response time and punctual. She dealt well with our dog’s feeding requirements. Took very good care of our dog, and we really appreciated it.

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Renee P.
Drop-In Visits
5.0 out of 5 stars

Cassidy goes above and beyond for our cat and our house! We feel SO comfortable knowing that she's taking care of everything.

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

Charlotte responded promptly with the shortest time possible and gave me some peace while I was away for an emergency. Tech was well well taken care off. Definitely recommend her for your pur

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

We had a great experience with Jessica and will definitely use her anytime we need a cat sitter. We were away for 5 days and she took excellent care of our 8 cats (including two 4 month old kittens). Jessica was very communicative and kept us informed if anything happened. After every visit, she sent photos of each cat and gave a summary of how the visit went. It was obvious that she genuinely cared about our babies and was attentive to their individual needs.

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

Brandie always does an amazing job with our pets. We know they’re in good hands when Brandie is taking care of them.

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Kelsey G.
Drop-In Visits
5.0 out of 5 stars

Lisa walked into a mess. It's my father's house who had lived in filth unbeknownst to me, as I live out of state. Despite this, she was kind and understanding. Would recommend to anyone!!!

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Jennifer H.
Drop-In Visits
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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

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Popular requests for pet sitting - Chester

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Chester average 7
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 $19.98 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 2,457 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:

  • 93% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 98% 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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