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 246
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.

1 / 1
Sitter Profile Image: Amanda B.
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Amanda B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
21 reviews
6 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: Indiana M.
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Indiana M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 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: Annabella C.
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Annabella C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
21 reviews
8 repeat clients
4 years of experience
North Chesterfield, VA, 23237

Annabella is great. She picked up a very short notice drop-in visit, and gave me and my wife peace of mind on our weekend trip. She followed every request I had exactly and I highly recommend her to anyone in need of a sitter!

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John W.
Sitter Profile Image: Abby M.
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Abby M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
282 reviews
98 repeat clients
14 years of experience
Chester, VA, 23831

Abby was very cool and understanding. I had a bit of a speedbump right before I left and she was cool with it. The dogs (Tuco and Bruschi) liked her immediately :) I was a bit nervous because I have not trained Tuco yet and he can be a lot to handle. Abby handled everything great!!! We would like to tip her, but I don't see a command button for this function on this page?? We all thank her... John, Fran, Tuco, Bruschi and Max the Cat

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John C.
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
210 reviews
59 repeat clients
10 years of experience
Chester, VA, 23831

Thank you for always being patient with our girl, and anticipating her needs on any given day. I also want to thank you for bringing our package in!

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Emily K.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
49 reviews
10 repeat clients
15 years of experience
Chester, VA, 23831

Excellent cat sitter. She came on time or even early to some of the appointments days. My cat Bonnie instantly loved her. My home was just as I left it when i returned. She was a pleasure to work with!

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Amanda B.
Sitter Profile Image: Phyllis N.
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Phyllis N.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
99 reviews
43 repeat clients
50 years of experience
North Chesterfield, VA, 23237

Phyllis was amazing and jumped in to help with a last minute family situation!! As someone who has been a petsitter on Rover, I couldn’t recommend her more 😊❤️

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Kellye M.
Sitter Profile Image: Cassidy R.
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Cassidy R.
from
$15
per visit
5.0 out of 5 stars
30 reviews
12 repeat clients
25 years of experience
Chester, VA, 23831

Cassidy was wonderful. There were daily updates and the cutest pictures. Even added a last minute walk since my pups were feeling cooped up. She let me know if there were any problems and I came home to happy pups.

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Manami H.
Sitter Profile Image: Crystal C.
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Crystal C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
291 reviews
103 repeat clients
15 years of experience
South Chesterfield, VA, 23834

Crystal was fantastic! We have 5 Pomeranians and were gone a week. She sent us photos of all of the pups each visit. Several have some problem behaviors and she gave us a number of very helpful training tips when she came to meet us and the dogs. It is VERY clear she understands how dogs think, understands their varied behaviors, needs, is patient, positive. They liked her immediately. She is reliable, was happy to bring in the mail and deal with the house alarm system. We were able to relax and completely enjoy our break, knowing they were in excellent hands. We recommend her most highly. Will definitely seek her out again when we next travel.

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Reid & Lori K.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$20
per visit
5.0 out of 5 stars
39 reviews
19 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: Lisa C.
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Lisa C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
70 reviews
21 repeat clients
40 years of experience
North chesterfield, VA, 23237

First time meeting Lisa for a drop in visit with our dogs and she is great . Asked great questions regarding dog care and she interacted well with my dogs . Would use her again !

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Kami J.
Sitter Profile Image: Jeanette A.
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Jeanette A.
from
$20
per visit
5.0 out of 5 stars
11 reviews
1 repeat client
30 years of experience
Chester, VA, 23831

About: For 30 plus years I had my own dogs from Rottweilers to peekapoos. Always had two so they had a buddy. Well trained where I didn’t need a leash. I babysit my friends dogs here at the house. I’m auntie. They go home spoiled. I travel a lot so, when my dog passed away I did not get another one. I work from home. I am empty nester who just went through a divorce. They can hangout with me all day. Ability to leave on the weekend to come back as required. Full fenced in yard. Traditional metal fence. With only two neighbors who have no animals. Quite neighborhood with a place to walk them around ponds.

Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$25
per visit
5.0 out of 5 stars
2 reviews
3 years of experience
Chester, VA, 23831

Rebecca cared for our three cats for about a week and a half, doing drop ins every other day. She was kind and communicative from start to finish, and went above and beyond to keep us and our kitties happy including lots of playtime, topping off food and water, and even watering a plant for us and bringing packages inside. Would book her again for future travel!

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Allison H.
Sitter Profile Image: Hailey S.
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Hailey S.
from
$15
per visit
5.0 out of 5 stars
3 reviews
15 years of experience
Chester, VA, 23831

Thank you for all your help you did so great with my precious Hank!

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Jordan C.
Sitter Profile Image: Darnell M.
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Darnell M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
101 reviews
38 repeat clients
14 years of experience
Colonial Heights, VA, 23834

Darnell took such great care of Monroe. He was very communicative and kind to my girl. She has separation anxiety so I was stressed leaving her at first l, but Darnell eased that very quickly. Will definitely book with him again in the future. Thank you Darnell!

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Alexandra P.
Sitter Profile Image: Lindsey R.
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Lindsey R.
from
$18
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
2 years of experience
Chester, VA, 23831

Lindsey was reliable and great with our “son”!! Sent us plenty of pics and gave him nice walks. Would definitely hire again.

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Kim R.
Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$25
per visit
5.0 out of 5 stars
28 reviews
12 repeat clients
23 years of experience
Chester, VA, 23831

We absolutely love how Tiffany takes great care of our little ones! She always updates us with fun & loving pictures. She is also very quick to respond with any questions or concerns & always on time!

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Calandria B.
Sitter Profile Image: Sarah K.
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Sarah K.
from
$20
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Chester, VA, 23836

Sarah was wonderful. She provided reliable top notch service. I highly recommend her and would use her services for my next request.

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Dwayne H.
Sitter Profile Image: Mia M.
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Mia M.
from
$20
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Chester, VA, 23831

About: Animals have been a massive part of my life for as long as I can remember, and growing up in a household with both dogs and cats taught me how to read their unique body language and personalities. Today, I am a proud pet parent to two wonderful cats of my own, so I know firsthand just how much your pets mean to you and the level of care they deserve. I have hands-on experience handling pets of all shapes, sizes, and ages, which includes raising a family dog from a puppy and training him to sit, as well as managing and pet-sitting two energetic 80-pound dogs simultaneously. I am also entirely comfortable with the less glamorous sides of pet care, as I am highly experienced in administering oral pills and various medications to both cats and dogs, maintaining strict routines, and handling unexpected bathroom accidents or cleanups calmly and thoroughly. I work full-time Monday through Friday, making my daytime availability perfect for early morning or evening walks, check-ins, and feeding routines. I am also available for overnight housesitting during the week, though this is typically best suited for independent adult animals who are comfortable being alone during standard work hours. My weekends are completely open and flexible for overnight care, extended daytime sitting, and drop-ins. Because young puppies require constant, round-the-clock supervision and undivided attention, I only accept puppy-sitting bookings strictly on Saturdays and Sundays to ensure your little one gets the dedicated care they need. Building a foundation of trust is my top priority when entering your home to care for your pets. For dogs, this means maintaining strict leash safety during walks, keeping a watchful eye for hazards, and following their established feeding and bathroom routines to minimize any anxiety. For cats, I prioritize a calm, respectful environment, giving them the space they need to feel secure while ensuring litter boxes are pristine and food is fresh. I treat your home with the utmost respect—keeping it clean, locking up securely, and handling unexpected messes or accidents quickly and thoroughly. Whether keeping a energetic dog safe on a walk or administering medication to a sensitive cat, I am committed to providing a secure, stress-free environment so you can have total peace of mind while you are away.

Sitter Profile Image: Abreya K.
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Abreya K.
from
$30
per visit
4.8 out of 5 stars
48 reviews
18 repeat clients
23 years of experience
Chester, VA, 23831

Abreya did well with my cat.

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Kiana D.
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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

Amanda was great with my dogs, and she had such a wonderful personality! I truly appreciated her care and would definitely book with her again.

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

Rebecca cared for our three cats for about a week and a half, doing drop ins every other day. She was kind and communicative from start to finish, and went above and beyond to keep us and our kitties happy including lots of playtime, topping off food and water, and even watering a plant for us and bringing packages inside. Would book her again for future travel!

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Allison H.
Drop-In Visits
5.0 out of 5 stars

Phyllis works well with my dog even though she can be a little sassy. I appreciate her patience and making sure my dog is taken care of. I highly recommend her.

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

We loved how Sabrina took care of our pets. She followed all of our instructions for their care and on a timely basis. We will probably be asking for her again.

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Suzanne F.
Drop-In Visits
5.0 out of 5 stars

This was my first experience with Rover and it couldn’t have gone better. Abby took wonderful care of my cat.

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Elizabeth V.
Drop-In Visits
5.0 out of 5 stars

Took care of a senior cat and an 8 week kitten. No problems. Good communication and a very pet friendly and caring personality

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Mark B.
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

Bella was very responsive and dependable. I have a very scared dog and she was very patient & kind with her. Will definitely book with Bella again!

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Shelby W.
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
5.0 out of 5 stars

She took a last minute booking as I had to run out for an emergency, A friend told me about her and she was nothing less than awesome Thanks!

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The V.
Drop-In Visits
5.0 out of 5 stars

Stephanie took extra special care of our 3 dogs. Even did some cleaning! I am so appreciative! Would love for her to take care of our babies again!

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

When we go out of town, we want to make sure our two cats are checked on by someone who genuinely cares for animals. Caitlin was a wonderful communicator and I didn't have to worry about our boys one bit while we weren't home. I'd be happy to ask for her help with them again, with either our cats or our dogs.

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Elisabeth & Chris B.
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 Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
  2. 2. Meet & Greet

    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

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 July 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 July 2026, there are 2,437 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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