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 288
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
• 46 reviews
19 repeat clients
20 years of experience
Chester, VA, 23831

“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.
Sitter Profile Image: Abby M.
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Abby M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 310 reviews
113 repeat clients
14 years of experience
Chester, VA, 23831

“Abby M. is great! She has been great with communication, easy to work with our ever changing schedules, and our dogs present happy and well-cared for. I definitely recommend her!”

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Barrie B.
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: Lisa C.
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Lisa C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 71 reviews
22 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: Airlea e.
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Airlea e.
from
$12
per visit
5.0 out of 5 stars
• 6 reviews
13 years of experience
Richmond, VA, 23237

About: I have over a decade of professional pet care experience as well as a lifetime of personal pet care experience. I prefer to work with the elderly or medically complex pets as I know they need special attention, adherence to routines, and a calm environment. I focus on providing fun daycare and boarding for pets that don’t do well in regular boarding facilities and require a more home-like experience. Prices are negotiable after a meet and greet. Please fill out your profile in full before meeting! Incomplete/no profile image profiles will not be given my address. I work from home so I spend a majority of my day with my pets and guest pets. Dogs are given mostly free range inside and allowed outside into the huge fenced yard many times a day. They get playtime with other pets and alone time when needed. Our yard is fenced and our house is doggy proofed to avoid trash cans, toilets, and non-chewable items from being accessed. Dogs are crated when they can’t be supervised.

Sitter Profile Image: Crystal A.
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Crystal A.
from
$25
per visit
5.0 out of 5 stars
• 15 reviews
10 years of experience
Chester, VA, 23831

About: I have taken care of dogs ranging from 10 pounds to 160 pounds my entire life. I have owned chihuahua dachshund mix, akitas, huskies, and German shepherds; so I understand big breeds as well as smaller ones. I have helped family members and neighbors with their dogs growing up with house sitting and dog walking. I know how important furbabies are to families, and treat each and every one as I would my own. I currently work full time with every other Monday off. I go to work about 7 am and get home about 430 pm. I do have volleyball leagues on Monday Wednesday and Friday nights that I am gone for 2 hours between 6-11pm as it varies based on game time. I love to hike and be outside so taking the dogs for walks a non issue. I treat all furbabies as if they were my own. I adjust my schedule accordingly to accommodate the animals as best as I can. I have given insulin shots and medication to animals and am comfortable with it.

Sitter Profile Image: Michelle H.
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Michelle H.
from
$25
per visit
5.0 out of 5 stars
• 13 reviews
7 repeat clients
25 years of experience
Chester, VA, 23831

“Michelle was great with my dog. We met ahead of time and I felt great about having her drop in while we were away. My dog got the break he needed and some playtime and treats as well. I would definitely recommend Michelle and would rebook next time I need someone.”

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Amanda H.
Sitter Profile Image: Meghan H.
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Meghan H.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
• 26 reviews
8 repeat clients
4 years of experience
Richmond, VA, 23234

“Meghan did a fantastic job with my dog. She was timely and followed his medical instructions since he’s on medication and is used to a certain schedule. She was great and I would hire her again!”

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Lenora H.
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.
Sitter Profile Image: Tianna L.
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Tianna L.
from
$28
per visit
4.5 out of 5 stars
• 8 reviews
2 repeat clients
5 years of experience
Courthouse, VA, 23832

About: I’ve taken care of my sisters dogs in the past, also owned many dogs growing up. My daughter LOVES them. My availability is pretty open! We would love to meet your furry friends. I’m in college and and i’m not currently working. My availability is open so that I will have plenty of time to care for your furry friend. We love animal's in my home we will treat them as our own of course. My place is clean and taken care of perfect setting.

Sitter Profile Image: Lashell D.
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Lashell D.
from
$35
per visit
5.0 out of 5 stars
• 32 reviews
6 repeat clients
15 years of experience
Chester, VA, 23831

“Lashell was great—prompt and excellent with communication. When Tut insisted on a short walk in the neighborhood, she was accommodating which was most appreciated. Will work with her again!”

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Christine H.
Sitter Profile Image: Taylor B.
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Taylor B.
from
$18
per visit
5.0 out of 5 stars
• 9 reviews
1 repeat client
5 years of experience
Henrico, VA, 23231

“Taylor is such an amazing pet sitter! She gives such great updates and takes so many pictures that I basically feel like I'm still home lol. I'd highly recommend Taylor and will be reaching out to her again for future needs.”

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Michelle W.
Sitter Profile Image: Rangeen A.
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Rangeen A.
from
$45
per visit
4.9 out of 5 stars
• 46 reviews
14 repeat clients
10 years of experience
Richmond, VA, 23237

About: I am a former dog owner who's trained a few dogs. I will treat the dog like my own! I understand the importance of routine, exercise, and cuddles! I work full time. Mostly from home. My significant other has an alternative schedule so the dog would be under 24 hour supervision. I can't wait to have a buddy with me throughout the day! I understand how anxious your paw partner may be while you are away -- I am here to console your paw partner until you are back 💕 I live in a single home with a large fenced backyard with a pool they can play in! Great parks and trails nearby. Dogs will have freedom in all rooms of the home. Dog will be supervised 20-24 hours a day. This helps me ensure pet safety and quick turnaround on any changes to health and/or behaviors.

Sitter Profile Image: Elizabeth J.
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Elizabeth J.
from
$20
per visit
5.0 out of 5 stars
• 3 reviews
25 years of experience
North Chesterfield, VA, 23234

About: My boy kitty passed away last year at 14 years old. He became very sick in his last 2 years so his care required daily shots, weekly vet visits. I became very proficient in giving pills by mouth as well. He was big and strong and didn’t like the vet or car rides so i learned how to best manage a very scared kitty. My mom had a senior dog who developed diabetes so I cared for him in my home for the last few years of his life. I gave him insulin shots twice a day and performed his medical care. I gave him meds by mouth and performed other care duties. I work part-time and am in school at ODU online so my hours are flexible. I live in the Richmond area and service a fairly wide range as I have my own reliable transportation. I prefer to pet-sit in the clients home as I have a cat myself. My grandma rescued hunting dogs, particularly hounds and beagles, when I was growing up, so I am safety minded when it comes to pets, especially ones who get scared easily.

Sitter Profile Image: Lilliana C.
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Lilliana C.
from
$20
per visit
4.8 out of 5 stars
• 11 reviews
6 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: Allejah K.
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Allejah K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 7 reviews
7 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

About: What sets me apart is my calm, low-stress home where I host max 2 compatible dogs at once. Perfect for anxious, selective, or reactive pups who need peace over chaos. I also offer solo-stay pricing for dogs who need to block my second spot. My experience shines with senior dogs (gentle mobility support, meds) and high-energy mediums (structured play without overwhelming them). I work less than 10 minutes from home and have a flexible schedule that allows me to check in during my breaks for walks, playtime, and potty breaks. While I’m away, I use indoor cameras to monitor pets and ensure their safety and comfort. I’m fully available and home on weekends, so your pup will get plenty of attention, care, and activity throughout their stay. I don’t have any pets of my own currently. I have a nice size fenced yard and I love taking pups on long walks in my neighborhood or at the local dog park if possible. You can also book my backyard on Sniffspot!

Sitter Profile Image: Michelle C.
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Michelle C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 19 reviews
3 repeat clients
15 years of experience
Midlothian, VA, 23832

“Michelle was diligent and caring while we were out of town for the weekend. We were able to travel with peace of mind due to her level of care. Will be rebooking!”

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Emilee O.
Sitter Profile Image: Lauren K.
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Lauren K.
from
$16
per visit
4.8 out of 5 stars
• 8 reviews
2 repeat clients
30 years of experience
Hopewell, VA, 23860

“Lauren was really great, especially given our cat is very skiddish/scared and runs under the sofa at the slightest noise. Thank you for being caring and compassionate. When we go out of town again, Lauren will definitely be our selection. We highly recommend her.”

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Brandon N.
Sitter Profile Image: Steph & Calvin Z.
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Steph & Calvin Z.
from
$22
per visit
4.7 out of 5 stars
• 14 reviews
3 repeat clients
20 years of experience
Chesterfield, VA, 23832

“Steph took absolutely wonderful care of my two pups! She was very communicative and a complete sweetheart! I’d definitely book with her again. Highly recommended :)”

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Cheayenne T.
Sitter Profile Image: Divine M.
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Divine M.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
3 repeat clients
4 years of experience
Richmond, VA, 23231

“Divine was very nice and gave my dogs all the love.”

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Katrina S.
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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

Indiana is clearly passionate about working with animals. She seemed excited at the challenge of winning over my nervous pit mix, which made us feel like this was the right fit! I’m looking forward to Norma having a sitter that not only tolerates her, but loves and appreciates her as we do.

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Emily K.
Drop-In Visits
5.0 out of 5 stars

Hi Sabrina, thank you so much for looking after our babies. We really appreciate you! Looks like cleo warmed up to you. Im glad the boys were excited to see you again!

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

I have been a repeat customer with Abby. She always does a great job with the dogs - definitely recommend her. =)

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

Trusted Phyllis so much so, we hired her again! Cant thank her enough for taking such good care of our fur babies! We always knew how they were doing at check ins 😊 Youre amazing Phyllis!!

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

We had such a great experience! She came over ahead of time to meet Duke, Winnie, and Green Bean, and immediately made us feel comfortable leaving them in her care. She was so kind, patient, and attentive with all three of our dogs and treated them like they were her own. You can tell she genuinely loves animals and takes the responsibility seriously. We felt completely at ease knowing our pups were being well cared for. We would absolutely recommend her and will definitely use her again!

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Lindsay Y.
Drop-In Visits
5.0 out of 5 stars

Our go to! She helped us in an emergency and worked around her schedule to be able to take care of our kitty. Thank you again!

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John W.
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

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
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  • 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?

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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

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Popular requests for pet sitting - Chester

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Sitters in Chester average 7
repeat pet sitting clients

FAQs for Pet Sitting - Chester

Frequently asked questions about Rover

The average cost of Pet Sitting in Chester is $20 per visit as of November 2026. Most bookings cost between $14 and $34 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 2,486 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:

  • 90% of sitters can help with special care needs
  • 94% 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 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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