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 29
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: Julia M.
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Julia M.
from
$22
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
20 years of experience
Campbell Hall, NY, 10916

It was our first time using rover so we didn’t know what to expect but we couldn’t have been happier! Julia is fantastic! We will be using her whenever she’s available.

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Shea O.
Sitter Profile Image: Jake F.
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Jake F.
from
$25
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Goshen, NY, 10924

Jake took very good care of my babies!

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Melanie V.
Sitter Profile Image: Eryn K.
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Eryn K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
188 reviews
57 repeat clients
5 years of experience
Florida, NY, 10921

I’m very happy with hiring Eryn for my anxious pup. She came by for a meet and greet before we solidified the dates she would come by for a visit which I appreciated. Milo is an anxious one, especially when he doesn’t know people & On Eryn’s first day alone with Milo, she stayed 30min longer so he could get to know her/ get used to her and there has been progress with every visit. She is detailed on her report cards which I appreciate and responds back to messages very quickly. She was also able to work well with my schedule! I will definitely continue to hire her when I’m in need of a visitation/walk so her and Milo can continue to bond! Thank you for your help this week, Eryn!

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Arianna H.
Sitter Profile Image: Mallory K.
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Mallory K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
52 reviews
25 repeat clients
20 years of experience
Goshen, NY, 10924

Mallory did a wonderful job taking care of the differing needs of both my pups. They were very comfortable around her and she handled their energetic personalities easily :)

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Lisette B.
Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
49 reviews
6 repeat clients
15 years of experience
Chester, NY, 10918

So amazing! Came and met us before the day of and notified me when she was there. Chip was a sleepy happy puppy when we got home! Definitely will use again ❤️

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Julia C.
Sitter Profile Image: Gavin O.
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Gavin O.
from
$16
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
5 years of experience
Chester, NY, 10918

About: I have personal experience with two dogs (Sunny and Roland) and a cat (Loki). Additionally, I have taken care of the pets of family and friends for years without complaint. I have worked as a dog sitter/walker for over 5 years now, and 3 of those on Rover. Unless my employment status changes, I am available 24/7 over summer, winter, fall, and spring breaks. My time is also very flexible and I don’t mind if I need to work at odd hours. I try to be as gentle and friendly as possible towards pets and will do more than the bare minimum when it comes to exercise and entertainment. I also have experience with cleaning up all kinds of potential messes.

Sitter Profile Image: Giselle G.
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Giselle G.
from
$25
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Goshen, NY, 10924

Giselle was absolutely amazing. She took such good care of our pugs, and she sent great photos everyday. We will definitely be using her again!!!!

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Missi M.
Sitter Profile Image: Linda B.
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Linda B.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
32 reviews
15 repeat clients
25 years of experience
Scotchtown, NY, 10940

This is the first time we used Rover and it was a very good experience. Linda took excellent care of our dog and 2 cats as well as our home. She checked in with pictures at each visit which enabled us to enjoy our vacation knowing our pets were in good hands. We will definitely ask Linda again to care for our pets in the future.

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Carolyn G.
Sitter Profile Image: Joseph G.
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Joseph G.
from
$20
per visit
5.0 out of 5 stars
51 reviews
17 repeat clients
2 years of experience
Chester, NY, 10918

Joseph was great. Very accommodating and responsive. Would book again.

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Sarah G.
Sitter Profile Image: Vicky A.
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Vicky A.
from
$25
per visit
5.0 out of 5 stars
16 reviews
7 repeat clients
15 years of experience
Middletown, NY, 10940

Vicky did an awesome job caring for Bruce. She was in communication with me and sent great pictures so I had complete peace of mind. I think Bruce really liked Vicky and the feeling was mutual. I highly recommend Vicky to care for your fur baby.

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Veronica W.
Sitter Profile Image: Amber C.
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Amber C.
from
$35
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
25 years of experience
Chester, NY, 10918

Thanks Amber for being so great to Oliver! He was so happy. You made our Christmas even better not having to worry about him!

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Karen M.
Sitter Profile Image: Shannon & Justin M.
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Shannon & Justin M.
from
$30
per visit
5.0 out of 5 stars
10 reviews
7 repeat clients
20 years of experience
Warwick, NY, 10990

Justin was reliable and got along great with my German Shepherd.

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Leilani W.
Sitter Profile Image: Carole S.
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Carole S.
from
$20
per visit
1 year of experience
Washingtonville, NY, 10992

About: Hi! I’m a devoted dog mom to Millie, my Cavalier King Charles Spaniel, and I bring that same hands-on care to every dog I look after. Raising Millie has taught me how much dogs thrive on consistency — reliable potty breaks, patient leash time, and reading their cues. I’m comfortable with feeding schedules and specific dietary needs, and I love a good sniff-led walk that lets a dog explore at their own pace. I’m patient, observant, and treat every dog’s home and routine like my own. Expect close attention to your instructions, thoughtful updates, and a sitter who genuinely loves the work. Looking forward to meeting your dog! 🐾 Pet care is already woven into my everyday routine — I’m home with Millie for feedings, potty breaks, and walks multiple times a day, so caring for a dog on a consistent schedule is second nature to me. I’m happy to build drop-in visits around your dog’s existing routine, whether that means a quick midday potty break or a longer afternoon walk. Since I’m mainly offering drop-in visits and walks, I focus on keeping things consistent with what your dog already knows — following their regular schedule, feeding routine, and any specific instructions closely. In my own home, I’m hands-on with Millie’s daily care, from meals to sniff-led walks, and I bring that same patience and attention to detail into your home so your dog feels comfortable and looked after.

Sitter Profile Image: Tina T.
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Tina T.
from
$18
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Monroe, NY, 10950

Tina was simply amazing and I cannot believe I found such a gem on this app. I have too much gratitude to express regarding her care of my life, my bay, my everything, a little chihuahua mix who I senior at 12 years old now with bad arthritis. I could tell from the minute I met Tina that she, like me, see dogs as human beings who just need consistent love, positive affirmation, attention and regular food/exercise care. My baby is very shy and shy around other dogs but she warmed up to Tina so so quickly, and was already crying when dropped off by Tina at home after Tina left her. I have the highest recommendation of Tina and even hesitate to post this bc I don’t want her to become too busy to take care of Nell again very soon and for a long time!

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Suzanne T.
Sitter Profile Image: Virginia V.
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Virginia V.
from
$18
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
6 years of experience
Goshen, NY, 10924

Virginia is reliable and so caring! Would definitely use her again!

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Rivka M.
Sitter Profile Image: Jill S.
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Jill S.
from
$25
per visit
5.0 out of 5 stars
175 reviews
46 repeat clients
57 years of experience
Washingtonville, NY, 10992

Jill was great! Very reliable, takes lots of pics, and took great care of our special needs cat during the Christmas holidays. I'm so glad I found her and will definitely be using her again next time we need a sitter. Thank you, Jill!

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Jennifer E.
Sitter Profile Image: Amy D.
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Amy D.
from
$30
per visit
4.8 out of 5 stars
35 reviews
11 repeat clients
20 years of experience
Goshen, NY, 10924

About: Hi! My name is Amy and I truly love dogs. I have taken care of several, many whom I have strongly bonded with and have learned a great deal. Your dog will be treated as if she/he were my own I will play catch and give lots of belly rubbing. We have many toys for them to play with. I will provide a safe environment for them. I *****Drop-off and pick-up times are flexible Please bring their food, poop bags, treats, and toys. For meet and greets, I am available during the week and all day on the weekends. I am home full time so can give you pup all of The attention and love they need! They will get plenty of playtime outside I have three very friendly dogs and a large backyard for them to run in. I go with the schedule you would like me to follow

Sitter Profile Image: Michael C.
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Michael C.
from
$25
per visit
4.9 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Florida, NY, 10921

Michael took care of our dog for 2 weeks while we were on vacation. We had him do drop in visits twice a day and he was amazing. He also watered our outdoor plants and did anything else we asked! He was responsible and very caring. Our dog absolutely loves him! We will call on him every time we go away. Thank you, Michael, for taking such good care of "our girl"!

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Angela A.
Sitter Profile Image: Jenna C.
Verified Background Check
Jenna C.
from
$25
per visit
4.6 out of 5 stars
18 reviews
3 repeat clients
10 years of experience
Chester, NY, 10918

Jenna was amazing! Our usual sitter had to cancel last minute after we had already left. Jenna accommodated a VERY last minute request and saved the day so we didn’t have to leave our event! She was reliable, caring, and gave us total peace of mind. Highly recommend her! Thank you Jenna!!

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Jill C.
Sitter Profile Image: Madeline B.
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Madeline B.
from
$20
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
18 years of experience
Goshen, NY, 10924

About: Hi there! My name is Madeline, and I would love to hear from you about your furry friend. I grew up surrounded by horses, dogs, and cats alike on farms across the Hudson Valley, which instilled a love for animals within me at a very young age. I understand that each client and animal requires an individualized approach. I am more than willing to listen to your desires and make adjustments to accommodate them to the best of my ability. I would consider myself quite the outdoorsy person, which makes me a great candidate to spend time with your animals. I am more than willing to answer any questions that you may have for me, and I look forward to hearing from you. I enjoy spending time with animals and ensuring they receive consistent attention, exercise, feeding, and affection. I plan my schedule to be sure every pet gets the care they need, whether it's walks, playtime, or simply keeping them company and comfortable. I care for every pet as if they were my own by following the owner's instructions carefully and maintaining their normal routine. I give pets plenty of love, attention, and positive interaction while respecting their individual personalities and needs.

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The median cost per visit for pet sitting in Chester is $25

Pet parents share their Rover experiences - Chester

1 / 1
5.0 out of 5 stars

Hailey did an amazing job with our cats while we were away. She came daily to care for them. She spent quality time loving on them and playing with them. She loved them like they were her own. She made sure their food was full and litter cleaned. I highly recommend her and will absolutely use her again to care for my fur babies.

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

We had an emergency pet request while we were out of town and Amber came at short notice, she is our pet hero! thank you so much Amber!!!!

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Adam 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
  2. 2. Meet In Person

    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

Popular requests for pet sitting - Chester

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Chester average 5
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 $33.3 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 2,532 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:

  • 94% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 97% 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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