Dog Sitting Chester

Book a Chester dog sitter to watch your dog in your sitter’s home or yours.

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Over 22
pet parents in Chester have booked dog sitting

Chester, Find top rated dog 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: Gavin O.
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Gavin O.
from
$16
per visit
5.0 out of 5 stars
3 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: Tessa D.
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Tessa D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
14 years of experience
Warwick, NY, 10990

About: I’ve been taking care of pets my entire life, and my family and friends look to me if they need me to dog sit (or pet sit) when they’re away or unavailable. I love animals, and so getting to take care of furry friends is an absolute treat!! I’m currently attending college, so monday and wednesday mornings im out of the house from 8-12. any other time, if given enough notice, i can be available for you and your pets! I live in a family home with my dog daisy, who is very friendly and about 14 years old now. She never fails to be entertained, and I love her with all my heart. I will do the same for your pets :)

Sitter Profile Image: Robbie O.
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Robbie O.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
30 years of experience
Campbell Hall, NY, 10916

About: I grew up on a dairy farm with all sorts of animals around. I have had many dogs, cats, parrots, chickens, rabbits, rats, and horses over the years. I have a degree in Equestrian Science and have taken care of animals my entire adult life. I have always been an avid hiker as well and love to take the pups on walks around the area. I currently own 3 dogs, a parrot, and 2 chickens and will give your animals the same love and attention that I give my own! I'm currently working part time and so have plenty of time to play with your fur babies. I am currently available for house sitting, drop in visits and dog walking. If your dogs get along with mine I might be able to do boarding as well. I have a dog door at my house with a fenced in yard along with 5 acres of fields to walk in. When coming to your home, I use my deep knowlege of dogs, cats, and other animals to keep your animals happy in their own home where your pets are MOST comfortable. They have the comfort of knowing they are safe in a place where they can learn to trust me and we can develop a bond so I can give your pets the same level of love and care as I would give my own pets.

Sitter Profile Image: Kacie B.
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Kacie B.
from
$20
per visit
1 repeat client
2 years of experience
Woodbury, NY, 10930

About: I’ve always had a genuine love for animals and enjoy spending time getting to know each pet’s unique personality. I’m patient, attentive, and focused on making pets feel safe, comfortable, and cared for while their owners are away. I have experience at the local animal shelter with dogs and cats of different ages and temperaments, including energetic puppies and more independent or senior pets. I’m especially mindful of routines, feeding schedules, and exercise needs, and I always aim to provide consistent care that matches what pets are used to at home. Whether it’s playtime, walks, or quiet companionship, I make sure each pet feels loved and well taken care of. Pet care fits naturally into my routine because I genuinely enjoy being around animals. I have a flexible schedule that allows me to provide consistent care throughout the day, including mornings, afternoons, and evenings when needed. I prioritize reliability and make sure I’m fully present during each visit or stay. Whether it’s daily check-ins, walks, or extended care, I’m able to adjust my time to meet the needs of both pets and their owners. I prioritize creating a calm, safe, and clean environment for every pet in my care. I follow all instructions carefully, including feeding routines, medication needs, and house rules. In a client’s home, I’m respectful of the space and make sure pets feel secure in their familiar surroundings. I always supervise interactions, ensure doors and gates are secure, and provide constant attention during visits or stays. My goal is to build trust with both pets and owners by being dependable, attentive, and caring at all times.

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: Nancy C.
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Nancy C.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
New Windsor, NY, 12553

I was very happy with my overall experience with Rover. It was easy to set up and choose someone to care for my 2 cats when I was out of town. Nancy was great! She came when she said she would and gave me updates at each visit. When I came home, the house was so calm and peaceful. The cats were safe, fed and happy. I would definitely recommend Nancy and will use her again in the future. Thanks! :) Rose G.

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Rose G.
Sitter Profile Image: Jacklyn S.
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Jacklyn S.
from
$30
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
23 years of experience
New Hampton, NY, 10958

Jacklyn was great! She always sent photos and played with my cat when she stopped in. I felt like my cat was very well taken care of and her communication was great.

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Allyson V.
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: Kristina G.
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Kristina G.
from
$24
per visit
4.9 out of 5 stars
13 reviews
4 repeat clients
24 years of experience
Mechanicstown, NY, 10940

Kristina took good care of my dog, she was always on schedule and kept me updated with my dog progress. My dog enjoyed seeing her every time for the daily check-in

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Maniessa G.
Sitter Profile Image: Maddy A.
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Maddy A.
from
$20
per visit
5.0 out of 5 stars
5 reviews
3 repeat clients
7 years of experience
Warwick, NY, 10990

In a last minute pickle, Maddy was quick to respond and did great with our dog.

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Carly K.
Sitter Profile Image: Julia R.
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Julia R.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
41 reviews
10 repeat clients
30 years of experience
Warwick, NY, 10990

Julie was the absolute the best! She went beyond and so much for our Crumpet. Kept in good contact the whole time and was there for us on short notice and on the holiday. Julie is the best! Will definitely use her service again, and recommend her to everyone!

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Matthew L.
Sitter Profile Image: Rhylee R.
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Rhylee R.
from
$25
per visit
5.0 out of 5 stars
20 reviews
4 repeat clients
8 years of experience
Montgomery, NY, 12549

Rhylee was thoughtful and kind and took great care of our pets. We are new to the area and needed some last-minute care, and she really came through in a pinch.

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Kait H.
Sitter Profile Image: Chris C.
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Chris C.
from
$40
per visit
4.9 out of 5 stars
41 reviews
13 repeat clients
35 years of experience
Monroe, NY, 10950

About: I am a children’s acting teacher that primarily works from home so I can spend lots and lots of quality time with your precious pup! I have a extremely safe and fun environment in Monroe on Mountain Lodge to share and plenty of stellar references from pups and their humans. If your loved one stays at my little cabin they get to walk daily with me to the one of the most BEAUTIFUL waterfalls!! I send lots of pictures if requested and my main goal is to make your lil loved one feel welcome while you go have fun!! About this sitter: I am a children’s acting teacher working primarily from home. I have over 30 years experience with animals of all types having been raised on a farm in Ga. I have plenty of experience with gentle training and specialize in pups with special needs. I offer a very safe and loving environment with lot of fresh air walks to a waterfall! I am a children’s acting teacher working primarily from home so I can spend lots of time with your precious pup or kitty! My main goal is to make them feel welcome with lots and lots of love I live in an extremely safe area on a dead end private road surrounded by beautiful woods and right close by to a waterfall! I’ve had MANY pups and kitties stay and their parents are thrilled by the area

Sitter Profile Image: Julia C.
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Julia C.
from
$15
per visit
5.0 out of 5 stars
3 reviews
10 years of experience
Monroe, NY, 10950

About: I have always walked and house sat for friends and family members that have multiple dogs, cats, rabbits and more. I have my own dog for over a year, and had family animals for my whole life! I will follow your schedule and pets needs as you instruct. I am comfortable walking on a leash, letting out in a yard, bathing and giving medicine as needed. I am a stay at home mom looking to get out of the house and make a few extra bucks at this time so whatever your need is, I will be there! I will make sure to send photos when I get there and communicate through the entire time. Any issues will be problems solved based on our previous conversations or I will reach out with any concerns.

Sitter Profile Image: Jade Marie C.
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Jade Marie C.
from
$19
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
4 years of experience
Middletown, NY, 10940

Jade was reliable and on time every visit. Thank you for caring for my boys

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Nik C.
Sitter Profile Image: Xiomara G.
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Xiomara G.
from
$30
per visit
5.0 out of 5 stars
25 reviews
7 repeat clients
15 years of experience
New Hampton, NY, 10958

Xiomara was an excellent cat sitter! She sent photo and video updates and was friendly and responsive. I will definitely be using her services again!

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Emily Kathleen W.
Sitter Profile Image: Alexis B.
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Alexis B.
from
$25
per visit
5.0 out of 5 stars
67 reviews
31 repeat clients
15 years of experience
Slate Hill, NY, 10973

I wish I could give Alexis more than 5 stars!!! I contacted Alexis last minute about day care for my two German shepherds, plans quickly changed because of my one of dogs health and she didn’t hesitate to offer to come to my house instead. My dog had an accident in my house and she thoroughly cleaned up after him. Alexis goes above and beyond for her clients and their pets from quick response times to genuinely caring for your pet. Keep up the great work and I look forward to booking again with you soon!

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Gianna L.
Sitter Profile Image: Meaghan D.
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Meaghan D.
from
$16
per visit
3 years of experience
Campbell hall, NY, 10916

About: I’ve grown up around animals and have years of experience caring for dogs of all sizes, ages, and personalities. Friends, neighbors, and family have trusted me to walk, feed, play with, and stay overnight with their pets while away. I’m comfortable with energetic puppies, senior dogs, and keeping pets on their normal routines. I’m reliable, attentive, and genuinely love spending time with animals, so I always make sure pets feel safe, cared for, and comfortable. I’m a recent college graduate currently studying for the LSAT, which gives me a very flexible schedule and plenty of free time throughout the day to care for your pets. I’m available for walks, drop-ins, and overnight stays during both weekdays and weekends, and I’m happy to work around your pet’s normal routine to make sure they feel comfortable and cared for. I always make sure pets feel safe, comfortable, and cared for whether I’m in my home or a client’s home. I pay close attention to each dog’s routine, energy level, and personality so they can feel as relaxed as possible while their owners are away. I’m responsible, communicative, and will keep you updated with messages and photos so you always know your pet is in good hands.

Sitter Profile Image: Maureen "Mo" S.
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Maureen "Mo" S.
from
$25
per visit
5.0 out of 5 stars
21 reviews
2 repeat clients
12 years of experience
Mount Hope, NY, 10940

Mo was that absolute best with our Skye Blue. She paid attention to her every need and was very informative. She sent pictures and we could tell how happy and loved Skye while we were away. Hands down we will booking Mo from now on. Book Mo, you won’t be disappointed.

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Shemeka N.
Sitter Profile Image: Natisha D.
Verified Background Check
Natisha D.
from
$100
per visit
4.8 out of 5 stars
77 reviews
36 repeat clients
2 years of experience
Middletown, NY, 10941

Perfect communication and reliability as always!

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Tania L.
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The median cost per visit for dog sitting in Chester is $25

Dog parents share their Rover experiences - Chester

1 / 1
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
1 / 1
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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
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Popular requests for dog sitting - Chester

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Sitters in Chester average 5
repeat dog sitting clients

FAQs for Drop-In Visits - Chester

Frequently asked questions about Rover

The average cost for Dog Sitting in Chester on Rover is $33.3 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 Dog 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 Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 2,436 sitters on Rover offering Dog 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.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Chester choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

A Meet & Greet is a short introductory meeting between you, your dog, 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Chester with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

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.

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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