Dog Sitting in Chester

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

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Top rated Chester dog sitters

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: Jervilyn J.
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Jervilyn J.
from
$35
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Warwick, NY, 10990

Jervilyn was wonderful with our two dogs! 🐕 We loved that she spent so much time interacting and playing with them. One of our dogs needed to be given medication and Jervilyn administered with no issues! Would definitely have Jervilyn drop in again!

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Kimberly A.
Sitter Profile Image: Julia R.
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Julia R.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
39 reviews
10 repeat clients
20 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: Samantha K.
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Samantha K.
from
$30
per visit
5.0 out of 5 stars
19 reviews
4 repeat clients
12 years of experience
Campbell hall, NY, 10916

Sammy is the absolute best in the area! She took such good care of our dog Ellie and we would use her services again in a heartbeat. We got lots of pictures of the visit, and she took her for a nice long walk. She definitely knows her stuff with dogs, and when she first met us and Ellie, she let Ellie warm up to her on her own terms and took her time. Before we knew it Ellie was curled up on her lap. We trust Sammy to watch her in the future and highly recommend all of her services! She is very flexible and accommodating as well. Very satisfied dog parents here!

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Kaleena A.
Sitter Profile Image: Robert L.
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Robert L.
from
$35
per visit
5.0 out of 5 stars
4 reviews
30 years of experience
Warwick, NY, 10990

Robert was a great dog care person! He gave our dogs special attention by interacting with them in play & extra pets and cuddles. Our dogs love Robert. Highly recommend.

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Kimberly A.
Sitter Profile Image: Natalie H.
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Natalie H.
from
$25
per visit
6 years of experience
Monroe, NY, 10950

About: From the age of 4 i’ve had two cats. Now I have two dogs as well. Both rescues one a mutt, and another a pit mix. Outside of my own pets I have taken care of friends, family, and neighbors pets. Whether it be walking, drop-in visits or staying overnight I love taking care of all animals. If needed, I can help medicate too. I have a flexible schedule and my own car. I’m here to be a last minute carer, or a reliable and stable carer for your pets. I am available for walking, drop-in visits, and overnight stays. With my own car I am willing and able to drive far distances. I will care for your pets by communicating clearly with you on any and all their needs. I will treat your home and your animals with care. I will love your pets like my own!

Sitter Profile Image: Kristina G.
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Kristina G.
from
$24
per visit
4.9 out of 5 stars
12 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: Jacklyn S.
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Jacklyn S.
from
$30
per visit
5.0 out of 5 stars
4 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: Alexa M.
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Alexa M.
from
$25
per visit
5.0 out of 5 stars
2 reviews
8 years of experience
10916

About: I have grown up with animals my whole life. I have been responsibly taking care of my dogs and cats on a daily basis. I have experience with a variety of dogs at all different ages. I’m also familiar with dogs who need special accommodations for medical conditions. I wholeheartedly love animals and would provide the utmost care to your pets that I would want for my own from a sitter. My schedule changes week to week, but generally I can be available in the morning, afternoon or evenings. Feel free to message about dates you need someone to care for your pet! I have plenty of experience dealing with animals and would want to create a safe environment for them. I would ensure that your pet is happy and cared for to the highest extent of the service. I’m happy to stick around to give your pets extra attention as well!

Sitter Profile Image: Colleen R.
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Colleen R.
from
$14
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
7 years of experience
New Windsor, NY, 12553

Super sweet gal!

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Allyson J.
Sitter Profile Image: Nancy C.
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Nancy C.
from
$18
per visit
10 years of experience
New Windsor, NY, 12553

About: I have experience with being around animals since I’ve been 5 years old. I have two dogs of my own and three cats as well. I will make sure the animals are comfortable, loved and taken care of properly. I am patient, caring, and have high energy. I am big on play time and walks and making sure they get their exercise for the day. I have walked dogs before and also provided in house care for several of my neighbors and close family friends. I really do enjoy being around animals and find it very relaxing. I’m a college student and can be very stressed at times so getting to play with an animal really is something I look forward to. Thank you (: On a daily basis I am always making sure my animals are fed, getting play time in, cuddles and more! They are so important to me! Making sure my pets always have water and their litter box is clean on a daily basis. I always ensure they get little extra treats throughout the day as well as cuddles!

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: Athena L.
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Athena L.
from
$20
per visit
10 years of experience
Warwick, NY, 10990

About: I’ve had a golden retriever, Toby, since I was seven years old and I love spending every moment with him! I’ve dog sat for my family members and friends many times and have dealt with dogs of all sizes and breeds! I’m currently in school right now so I am available any weekday after 4:30 and all day on weekends. I am very flexible with my schedule. I have an open back yard where my dog can roam and I can play fetch with him, I also sometimes talk him to the dog park and run with him there!

Sitter Profile Image: Sophie G.
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Sophie G.
from
$30
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
13 years of experience
Middletown, NY, 10940

You’re amazing, thank you so much!!! Last minute and in a bind, you really came through🫶🏼

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Abby Q.
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: Ryan S.
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Ryan S.
from
$20
per visit
12 years of experience
Harriman, NY, 10926

About: I have a 6 year old pit mix who I’ve raised since she was 8 weeks old and previously had two family dogs since the age of 3. I’ve never experienced living with out a dog/pet and I’ve grown to love every second of it. Not only do I have experience with my own pets but I have helped out my neighbors in the past taking care of their dogs as well. I work full-time but I am available most week day evenings and most Tuesday mornings. I am also available for walks during select weekends as needed I can help provide walking, feeding, playing, or whatever fits the needs of you and your pet in a safe and fun environment at your home

Sitter Profile Image: Bri S.
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Bri S.
from
$20
per visit
5.0 out of 5 stars
1 review
1 repeat client
7 years of experience
Middletown, NY, 10940

About: Hi! Me and my boyfriend Jerry just started rover together ( i have had an account with rover for a little over 5 years i did rover on a side years ago and also worked for my sisters dog walking business in the city as well!! ) We’re a reliable, animal loving couple with years of experience caring for pets. We both grew up with family dogs and currently have two cats together ! ( no dogs yet unfortunately until we move into an apartment that allows us to 😔) one we’ve had for over two years and another we recently fostered and welcomed into our home a little over 3 months ago . We treat our pets like family and understand how important it is to have someone trustworthy caring for yours. We both work mornings full-time and are looking to spend our extra time doing something we genuinely enjoy — walking dogs and caring for pets!! we would love to meet your fur babies please message us with anyyyy questions or concerns ! :) We both work full-time at our family owned bagel shop café during the mornings, so we’re available for afternoon and evening walks, drop-ins, and pet care! We typically get out of work around 3 PM during the week and 2 PM on Sundays. We’re also off every Wednesday and every other Saturday, which gives us extra flexibility for longer visits or weekend care. We’re dependable, responsive, and excited to spend our free time caring for pets! Please message me to see if we can work something out!! i will be sure your babies will be in a clean & safe environment & will always make sure you know what’s going on, also that your dog gets all the attention i can give ! 🥰 we love to provide as many photos to provide peace of mind ( i know when i leave my babies with a sitter the photos always help me feel at peace)

Sitter Profile Image: Kamille W.
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Kamille W.
from
$30
per visit
4.9 out of 5 stars
19 reviews
3 repeat clients
15 years of experience
Goshen, NY, 10924

Used Kamille for the first time for my puppy for a drop in visit. She was quick to schedule a meet and greet once I contacted her, I could tell she was good with animals as soon as I met her. The visit went very well, she did everything that was asked and I could tell my puppy was very happy when I got home. The report card was detailed and let me know exactly how things went.

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Elissa L.
Sitter Profile Image: Maddy A.
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Maddy A.
from
$20
per visit
5.0 out of 5 stars
4 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: Madison F.
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Madison F.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
3 years of experience
University, Newburgh, NY, 12550

About: I’ve owned dogs that I have actively taken care of for years now! Raising my own boxer puppy and helping out family and friends by dog sitting and taking care of dog their dogs for them! I’m currently a freshman at UB! My classes are pretty short and spread out throughout the day! I would have ample time to check on your dog multiple times day! I am also available almost every weekend! I can actively take your dog out, play with it, take it for walks! Whatever is needed to make sure your dog is in a good environment!

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

I am sorry that I am always late with my tip. We are so grateful to have Mo to help care for our dog we go away! She is very attentive to the smallest details!

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Barbara H.
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Chester dog parents share their Rover experiences

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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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog sitting in Chester is $25

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Chester average 5
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Chester on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Chester dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,457 dog sitters in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 86% of Chester dog sitters respond in under an hour.

Dog sitters in Chester have an average of 16 years of experience. Dog sitters with repeat customers have an average of 5 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Chester.

Rover makes it easy to find Chester dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 2,457 dog sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 97% of dog sitters offer daily exercise, 96% offer medication administration, and 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.