Pet Sitting Cheshire

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 92
pet parents in Cheshire have booked pet sitting

Cheshire, 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: Justin B.
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Justin B.
from
$13
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Wallingford, CT, 06492

About: I started taking care of pets when we got a family dog when I was a kid. Since then, I help my mom with her pet-sitting business and have sat for her 3 dogs for a week+ at a time. I genuinely love taking care of dogs of all ages. I work a full-time job 7-3 M-F, and have afternoon pilot classes about twice a week, always scheduled in advance. Occasionally I go out of town for a weekend, again, scheduled well in advance. I would treat a client's pet as if they were my own, which is to say with lots of love, care, patience, respect, and kindness. And a lot of head pats (if and when applicable).

Sitter Profile Image: Darya H.
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Darya H.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
Prospect, CT, 06712

Darya has done a great job taking care of our corgi puppy! She is always on time and gives a thorough daily update for her drop-in visits. We have appreciated how she follows our detailed instructions and is very responsive. We would definitely recommend Darya!

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Madeline P.
Sitter Profile Image: Erin M.
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Erin M.
from
$15
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
40 years of experience
Wallingford, CT, 06492

Erin took amazing care of our 3 babies. She was extremely quick to respond and would spend 30-45 minutes with our dogs each visit and kept them company. She was very understanding when our plans would change slightly and had no issues adjusting the schedule. Highly recommend.

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Allie K.
Sitter Profile Image: Deborah W.
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Deborah W.
from
$20
per visit
5.0 out of 5 stars
7 reviews
10 years of experience
Cheshire, CT, 06410

Deb was great with my energetic pup! She was very communicative throughout the whole process and provided updates during drop-in visits. I would highly recommend her and will definitely a repeat customer in the future!

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Jessica H.
Sitter Profile Image: Julie R.
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Julie R.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
73 reviews
30 repeat clients
20 years of experience
Meriden, CT, 06451

We absolutely adore Julie. She took her time and not only had no problem with our cat's semi complicated meal routine, but she sat with our very needy cat and gave her undivided attention while we were away. We will absolutely be contacting Julie anytime we are going to be away and need our pets to be taken care of.

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Tova H.
Sitter Profile Image: Susan B.
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Susan B.
from
$20
per visit
4.9 out of 5 stars
10 reviews
4 repeat clients
40 years of experience
Cheshire, CT, 06410

Susan and her husband were lovely. The dogs were well taken care of and happy when we returned home. We will be calling on them again 🐾

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Stephanie H.
Sitter Profile Image: Hailey T.
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Hailey T.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
81 reviews
24 repeat clients
10 years of experience
Meriden, CT, 06451

Hailey is the person you want your pets to see while you’re away. My boys immediately took to her and were happy to see her stop by. Hailey has such a warm and calming presence that made them both comfortable. I appreciated her communication with me to let me know how the visit was going as well as the videos and photos she sent over. This would have been a 10 star rating if this app had that option :)

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Kellsie P.
Sitter Profile Image: Karen M.
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Karen M.
from
$35
per visit
5.0 out of 5 stars
35 reviews
12 repeat clients
25 years of experience
Cheshire, CT, 06410

About: Hi, I have been taking care of animals for over 25 years now. I also use to breed German Shepherds for eight years. I am a stay at home mom and Rover, is my full time job now that my kids are teens. I use to foster dogs and other animals before I had a family and worked on two farms, So I have a lot of experience with different types of breeds, temperaments, past abuse, and very skittish animals. I have much confidence when it comes to taking care of special case dogs, senior dogs, newborn/Whelping puppies and more. We live in a house with over two acres of land, with lots of lovely areas to walk, including a cemetery that is located over the fence in our yard. It has lots of roads that are quiet and safe. I find this great because they gets lots and lots of exercise, and its great for dogs that may be frightened of loud, busy streets, or leash reactive dogs. We also have doggie pools ,( when it's hot) if your pup loves water play! My German Shepherd and Papilions are highly trained and socialized . They are extremely well behaved, as well as amazing house dogs and companions to my autistic son. HOWEVER, your dog/s and my dogs will NEVER come in physical contact with each other. . We are highly active family, so lots of play and exercise fits in our schedule everyday. While hosting your pets at my house, they will receive the same attention and affection as if they were my own dogs. I always sleep in the same room as the pups ( unless told otherwise) to keep they company and comfortable during their stay. We will have lots of potty breaks, keep right on track with feeding schedule. Everyday we will have lots of play time, down relax time, and brain stimulating fun as well. I will take them on long walks at the cemetery that is behind the fence of our home. I ONLY do family boardings, I do not mix other family dog/s. I find no matter how socialized they are, being away from home on top of being with unfamiliar dogs can always have a possibility of disaster. My goal is to keep everyone safe! I will take up to 2 dogs from the same family. Thank you for understanding. I absolutely am an animal lover, and it's the only job that makes me feel happy, confident and I have such a passion for this work So your pets will become my family when they are with me. I will always protect them and care for them like they are my own. I will always send pictures and videos of your furbaby while they are in my care. I am very good at keeping in contact with of my clients via their choice of email, text message or phone/video calls. Please ask me as many questions as you like, I am eager to learn about your fur babies! My dogs are on strict, daily routine that doesn't interfere with my work schedule. However my dogs and your dog/s will not come in physical contact with each other. We have two wings of our home and the main house where are dogs are. Down the hall we have the ..... Huge Doggie Suite!! Equipped with a mini fridge for meds and wet food, with lots of toys, beds,blankets, a big doggie couch, Sink, Raincoats and snow jackets, AC AND HEAT. Lots of windows and sky lights, screen windows to slide open to get that fresh crisp air in the morning and gentle breeze at night. Spring and Fall are best for those times. But we will have fun all year round because I am a huge outdoors person. I also have doggie Tv playing everyday!!😊 My schedule most of the time will be wide open, which only a few days here and there that I won't be available. I will follow all your directions to a T, and you will never be disappointed by my services! I look forward to all my new pup and "hooman" clients.

Sitter Profile Image: Michael F.
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Michael F.
from
$15
per visit
5.0 out of 5 stars
4 reviews
15 years of experience
Cheshire, CT, 06410

About: If I can manage 30 middle schoolers, I can handle your dog." Hi there! My name is Michael, and I am a Cheshire local with 18 years of experience as a teacher, a dad of three kids, and most importantly — a dog dad of two. Caring for animals is not a side hustle for me; it is simply an extension of the way I live my life. My two dogs, Laney and Monster Truck, are at the center of our family. They go on walks, they cuddle on the couch, and yes — they are absolutely spoiled. When your pet stays with me, they become part of that same routine. What you can expect from me: 📍 Daily photo and text updates — I know you miss them. 🏡 A home environment with a yard, kids, and two friendly resident dogs. 🚶 Regular walks, playtime, and one-on-one attention. 🧠 Patience, structure, and consistency — 18 years in a classroom will do that to you. 💬 Clear, prompt communication before, during, and after every booking. A little more about our home: I am available primarily on weekends and summers, which means when I have your pet, I am fully present — not squeezing in visits between a 9-to-5. Your dog gets my undivided attention. I have experience with dogs of all sizes and energy levels. My own two dogs are a larger weiner dog and a medium sized hound/boxer mix, so I understand what it means to manage both ends of the spectrum. Whether you need a dog walker, a drop-in visit, or a full boarding stay while you travel, I would love to meet your pup. Let's set up a free meet-and-greet so your dog can check me out first. Your pet deserves someone who treats them like part of our pack. Pet care is already woven into my daily life. As a dog dad of two, my mornings start with a walk and my evenings end with one. Adding your pet to that routine is natural and effortless for our family. On weekends and during the summer — when I am available for bookings — I am home and fully present, which means your dog is never an afterthought. They are part of the day from start to finish. What you can expect from me: 📍 Daily photo and text updates — I know you miss them. 🏡 A home environment with a yard, kids, and two friendly resident dogs. 🚶 Regular walks, playtime, and one-on-one attention. 🧠 Patience, structure, and consistency — 18 years in a classroom will do that to you. 💬 Clear, prompt communication before, during, and after every booking.

Sitter Profile Image: Tatum D.
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Tatum D.
from
$17
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Meriden, CT, 06451

Tatum was soooo great with my quirky dog! She totally went above and beyond to make sure my nervous nelly was comfortable enough to eat and do her business. She also kept me updated on everything that was going on with my pup and my kitty. I’ll definitely work with Tatum again!

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Alexis G.
Sitter Profile Image: Crystal Z.
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Crystal Z.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
16 years of experience
North Haven, CT, 06473

Crystal was absolutely amazing with ELLA. ELLA took to Crystal as if she had been a part of our family forever. She was kind and nurturing understanding and genuine. I highly recommend Crystal.

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Marcia I.
Sitter Profile Image: Mckenzie P.
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Mckenzie P.
from
$18
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
4 years of experience
Southington, CT, 06479

We had such a great experience with Mckenzie! From the very beginning, she was communicative, reliable, and clearly loves what she does. It gave us so much peace of mind knowing our puppy was in good hands. We also loved the photo updates. We came home to a relaxed, happy puppy, and that says everything. We would absolutely book with her again and highly recommend her to anyone looking for a trustworthy and caring sitter!

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Courtney L.
Sitter Profile Image: Rebecca F.
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Rebecca F.
from
$25
per visit
5.0 out of 5 stars
25 reviews
11 repeat clients
20 years of experience
Wallingford, CT, 06492

I highly recommend Rebecca! Everything went very smoothly and she made my family’s time away stress free. She took care of my two dogs and it was clear they were in good hands! She sent several pictures with her updates which was awesome!

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Kara O.
Sitter Profile Image: David P.
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David P.
from
$38
per visit
5.0 out of 5 stars
37 reviews
13 repeat clients
20 years of experience
Cheshire, CT, 06410

Dave is a top notch sitter. I love to receive his reports of how the visit went. He notices the details. My dog is always so happy to see him. I can’t recommend Dave enough!

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Jaclyn W.
Sitter Profile Image: Michael D.
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Michael D.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
25 reviews
11 repeat clients
20 years of experience
Southington, CT, 06489

Michael was great. Jax loved him. Michael went above and beyond to make sure Jax got the attention he needed. And we always got good feedback from each visit.

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David S.
Sitter Profile Image: Sabrina & Daniel S.
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Sabrina & Daniel S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
153 reviews
62 repeat clients
10 years of experience
Wallingford, CT, 06492

We were so impressed with the care that Sabrina & Daniel gave to our dog Winston! He can be shy at first, and Sabrina & Daniel gave him the space he needed to get comfortable - so much so he was asking for pets by the middle of the hour. It feels so nice knowing our dog is in good hands while we have to be away from him. Thank you both for your sweetness toward Winston, your reliability and professionalism. Winston can't wait to see you again soon!!

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Christina W.
Sitter Profile Image: Alexandra C.
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Alexandra C.
from
$20
per visit
14 years of experience
Cheshire, CT, 06410

About: Grew up with four dogs and lifelong pet care experience. Trusted by clients & friends. Skilled with French Bulldogs and Dachshunds, including IVDD-aware handling. Attentive, reliable, communicative! Pet care easily fits into my routine. I have a flexible schedule and am available any day, ensuring pets receive reliable, attentive care whenever needed. I carefully follow each owner's instructions, maintain pets' routines, provide plenty of attention, exercise, feeding, medication if needed, and keep their home clean and secure.

Sitter Profile Image: Jordyn K.
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Jordyn K.
from
$20
per visit
5.0 out of 5 stars
4 reviews
21 years of experience
Cheshire, CT, 06410

This was my first time using rover and leaving our cats alone this long but Jordyn was honestly so great. During the meet and greet the cats immediately liked her. And for each drop-in Jordyn sent us multiple pictures and a description of the visit which made being away so much easier. I would highly recommend her to anyone needing cat care.

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Kelli H.
Sitter Profile Image: Hunter D.
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Hunter D.
from
$18
per visit
4 years of experience
Cheshire, CT, 06410

About: I've taken care of dogs since I was a freshmen in high school. My jobs consisted of walking, feeding, playing, and occasionally staying overnight with the dog. I love animals and genuinely care for them, making my service just a bit more special. Currently I only work after 3:45 on weekdays, so I have plenty of time to hangout with your pups! I have enough time for attentive care and multiple visits per day! I do not intend to board any dogs in my home, but I can crate a dog, I am comfortable with fenced in backyards for unleashed pups, and when no fence is available the dog will be leashed/harnessed.

Sitter Profile Image: Tom F.
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Tom F.
from
$25
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
30 years of experience
Cheshire, CT, 06410

Tom and his oldest daughter took excellent care of our 2 cats when we were out of town! They quickly became comfortable with them which is a testament to how much they love animals. We will certainly be using them again in the future!

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Marc M.
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The median cost per visit for pet sitting in Cheshire is $25

Pet parents share their Rover experiences - Cheshire

1 / 1
5.0 out of 5 stars

Lori was fantastic! She provided the highest level of care while we were away for a week, and always sent photos and videos during each visit. Luna was clearly comfortable and happy and we will definitely book again for future needs. Highly recommend booking with Lori!

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Megan D.
Drop-In Visits
5.0 out of 5 stars

This was my first time using rover and leaving our cats alone this long but Jordyn was honestly so great. During the meet and greet the cats immediately liked her. And for each drop-in Jordyn sent us multiple pictures and a description of the visit which made being away so much easier. I would highly recommend her to anyone needing cat care.

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Kelli H.
Drop-In Visits
5.0 out of 5 stars

Christine was from the start very thorough, detail oriented and very caring. This was our first experience with her and she did not disappoint. Christine is a very kind and thoughtful person and it showed in her daily reports and photos she sent. She cared for our kitties for 10 days and they are not used to being alone for that long. Christine took extra care to be sure they knew she was there to help them without overwhelming them. We felt very comfortable that they were going to be in good hands and we know they were. Thank you Christine! Will definitely be booking with you again.

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Mary Kay H.
Drop-In Visits
5.0 out of 5 stars

Dave is the best! My dog is always so happy to see Dave when he comes over. I really appreciate and enjoy his notes and comments after his drop ins and walks. I’d give him 10 stars if I could.

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Jaclyn W.
Drop-In Visits
5.0 out of 5 stars

Katherine is incredible. She is extremely flexible and reliable. My 3 dogs have different personalities and she was able to connect with each of them. She made sure I home from my trip and the dogs were being taken care of. I highly recommend her.

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Maureen H.
Drop-In Visits
5.0 out of 5 stars

Samantha was fantastic! I would have her watch my dog and cats again in a heartbeat. She’s great with animals and a very sweet person too.

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Adrienne D.
Drop-In Visits
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Sitters in Cheshire average 5
repeat pet sitting clients

FAQs for Drop-In Visits - Cheshire

Frequently asked questions about Rover

The average cost for Pet Sitting in Cheshire on Rover is $18.87 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 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 August 2026, there are 2,950 sitters on Rover offering Pet Sitting across Cheshire. 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 Cheshire 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 Cheshire. On Rover:

  • 95% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% 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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