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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Chester, Find top rated pet sitting

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
$30
total per visit
5.0 out of 5 stars
• 165 reviews
46 repeat clients
12 years of experience
Becket, MA, 01223

“Kathleen is hands down the best dog sitter! We felt so at ease leaving him with her for the day. Sampson had the BEST day and was the happiest pup when we came home. Thank you for taking such good care of him. :)”

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Jillian H.
Sitter Profile Image: Janet M.
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Janet M.
Star Sitter
$34
total per visit
4.9 out of 5 stars
• 18 reviews
8 repeat clients
53 years of experience
Chesterfield, MA, 01012

“Janet was very communicative & understanding of my shy girl. You can tell right from the meet & greet she is very sweet and caring with animals. She was available at a last minutes notice and followed detailed instructions. Will definitely have her back! Thanks Janet!”

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Sarah D.
Sitter Profile Image: Taylor W.
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Taylor W.
Star Sitter
$27
total per visit
5.0 out of 5 stars
• 21 reviews
9 repeat clients
20 years of experience
Lee, MA, 01238

“Taylor was delightful to deal with. She was prompt, professional and yet warm and friendly. She went the extra distance to clean up around my dog's bowl after meals and seemed very focused while still being engaging and playful with my 16 month old Maltese. I look forward to reaching out to her the next time I will be in her area. She's the kind of young woman who breeds confidence in me that my little one is in good hands! Highly recommend Taylor!”

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Elizabeth S.
Sitter Profile Image: Eliza W.
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Eliza W.
$12
total per visit
15 years of experience
Westfield, MA, 01085

About: I have had all animals of all kind since I was a little kid. I first started dog sitting when I was 11 and have worked as a farm manger and farm sitter throughout the last four years of college in South Carolina with my one year old Vizsla Juno. I have just moved back to Massachusetts, where I grew up, to attend law school and would love to spend time with your pups! I am spending the year studying for the LSAT’s and will be available during week days and weekends for walks and overnight pet sitting whenever you need. I have two very friendly vizslas who love to play and go for walks of hikes with other dogs. I have cared for all kids of dogs including elderly, rehabbing, reactive, and puppies. I am completely committed to keeping your dogs safe and happy life they are my own.

Sitter Profile Image: Mitchell L.
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Mitchell L.
$12
total per visit
26 years of experience
Westfield, MA, 01085

About: I’ve had cats and dogs and I’ve taken care of them and loved them for forever. I’ve recently adopted two kittens and I love to play with them. I’m a student right now with a flexible schedule so I could check in on pets on pretty much every day and throughout the day. I have energy to play with young cats or dogs and can fulfill all their needs. My services will change depending on the pets personality and what they’re needs are.

Sitter Profile Image: Brendon P.
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Brendon P.
$20
total per visit
5.0 out of 5 stars
• 89 reviews
18 repeat clients
40 years of experience
Westfield, MA, 01085

“Brendon has always been great with my dog. He is also very responsive and easy to work with especially considering my weird work schedule and I greatly appreciate his help!”

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Ben G.
Sitter Profile Image: Wendy A.
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Wendy A.
Star Sitter
$17
total per visit
4.9 out of 5 stars
• 7 reviews
3 repeat clients
30 years of experience
Westfield, MA, 01085

“Wendy was punctual, communicative and reliable with our last minute request on a holiday. Really grateful for her service and adorable pictures of our dog, Shadow. We will definitely use her in the near future.”

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Colin & Maria G.
Sitter Profile Image: Paisley R.
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Paisley R.
Star Sitter
$23
total per visit
5.0 out of 5 stars
• 21 reviews
5 repeat clients
10 years of experience
West Springfield, MA, 01089

“Paisley was very reliable, timely with visits, and loving to our pups. Paisley gave detailed updates with great photos so it seemed like we never left! I will definitely book again with Paisley for future dog care needs.”

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Mikenzie M.
Sitter Profile Image: Renee M.
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Renee M.
$23
total per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
5 years of experience
Westfield, MA, 01085

“She was awesome, communicated very well and took good care of my pup.”

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Nathan P.
Sitter Profile Image: Clara M.
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Clara M.
$50
total per visit
5.0 out of 5 stars
• 17 reviews
3 repeat clients
11 years of experience
Tyringham, MA, 01264

“Clara was so wonderful with our animals, very responsive, trustworthy, and friendly. She made it so our trip away (during a snowstorm nonetheless) was as stress free as possible. We were nervous about the weather and her access to the property and the added challenges the storm brought, but she handled it no problem. We are really excited to have someone we can rely on in the future to take care of our furry friends while we’re away.”

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Shawn M.
Sitter Profile Image: Kelly H.
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Kelly H.
$73
total per visit
5.0 out of 5 stars
• 66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

“As always, our dogs were SUPER excited to see Kelly!”

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Eric L.
Sitter Profile Image: Trista S.
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Trista S.
$28
total per visit
5.0 out of 5 stars
• 24 reviews
10 repeat clients
30 years of experience
Pittsfield, MA, 01201

“Trista was wonderful! She sent great pictures of all the pets. They all look so happy and well cared for. Great communication and followed all instructions. You can tell she really cares for your pets. We would highly recommend! 😊”

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Alana L.
Sitter Profile Image: Julie G.
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Julie G.
Star Sitter
$25
total per visit
5.0 out of 5 stars
• 16 reviews
2 repeat clients
4 years of experience
Holyoke, MA, 01040

“Great communication!”

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Meagan D.
Sitter Profile Image: Ace G.
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Ace G.
Star Sitter
$28
total per visit
5.0 out of 5 stars
• 68 reviews
22 repeat clients
9 years of experience
Chicopee, MA, 01020

“Ace was super gentle and patient with my anxious shy guy! He took a liking to Ace quickly— not the norm for my dog. Ace was communicative and took great pics of my boy. Thank you Ace!! Will 100% book again soon ☺️”

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Stephanie H.
Sitter Profile Image: Matt L.
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Matt L.
Star Sitter
$34
total per visit
4.9 out of 5 stars
• 78 reviews
19 repeat clients
32 years of experience
Hadley, MA, 01035

“Wonderful visit and walk. My pet seemed very happy and he was very accommodating to book last minute. My pet instantly liked him, like he has a way with pets.”

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Jimi O.
Sitter Profile Image: Valentina M.
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Valentina M.
$23
total per visit
5.0 out of 5 stars
• 2 reviews
6 years of experience
Stockbridge, MA, 01262

About: I grew up with 2 dogs and 2 cats. My family was part of helping a farm when i was little, I got to take care of ducks. They were so cute. I love animals and let me know if you had questions. I work at Marshall’s. I will be taking care of the animals during my days off. I will make sure they have everything they need I grew up with cats and dogs. I love all kinds of animals. I will take good care of them. I can bring them to my house as well.

Sitter Profile Image: Angela G.
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Angela G.
$23
total per visit
10 years of experience
West Springfield, MA, 01089

About: I’ve taken care of dogs for many years now, my aunt had very sweet german shepard that I would always walk, feed and play with. And now my family has our own dog that we love and care for very dearly! I currently work full-time, but I would be more than happy to take care of your furry friends on any of my days off or any afternoons I’m free!! My cat is indoors, but she always has food and water available, and lots of toys that’s she loves to play with! No fenced yard, but it is big and we have a very long leash that we use to play fetch with! And of course, lots of walks!

Sitter Profile Image: Reymon B.
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Reymon B.
$30
total per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
20 years of experience
Pittsfield, MA, 01201

“Lovely, high energy, reliable Dog Sitter! Looking forward to having Reymon again.”

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Elizabeth S.
Sitter Profile Image: Lydia H.
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Lydia H.
$40
total per visit
5.0 out of 5 stars
• 19 reviews
5 repeat clients
7 years of experience
Easthampton, MA, 01027

“Lydia is the best!! She goes above and beyond to make my kitties and I are happy! Excellent communication, warmth, dedication, and professionalism! I truly wish she wasn't moving away, but I understand that she is going to make a huge difference in many human and nonhuman lives as she pursues higher education! I cannot recommend Lydia enough!”

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Steven D.
Sitter Profile Image: Amad E.
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Amad E.
$32
total per visit
5.0 out of 5 stars
• 34 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

“This is the second time that I used Amad to care for my cats, he has been great, will stay and play with them, easy to reach and will quickly respond . Overall we highly recommended .”

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Fabiola C.
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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

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FAQs for Pet Sitting - Chester

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a 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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