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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Cheshire, 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: Olivia S.
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Olivia S.
Star Sitter
$17
total per visit
5.0 out of 5 stars
• 41 reviews
15 repeat clients
1 year of experience
Adams, MA, 01220

“Olivia is the best. She stopped by twice a day to feed and spend time with my cat. My cat absolutely loved her. Olivia went above and beyond by getting my mail and stopping by an extra time to change out a food bowl because my cat didn’t like that particular bowl. Cats…. 🙄 am I right? Thank you Olivia! I will definitely be contacting her in the future.”

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Kaitlin S.
Sitter Profile Image: Zoey L.
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Zoey L.
$23
total per visit
5.0 out of 5 stars
• 2 reviews
10 years of experience
Cheshire, MA, 01225

About: I have pet/house sat multiple times over the past several years for friends and family, and have worked with several types of animals from small critters like guinea pigs and ferrets, cats, and even large dog breeds. I also have 2 years experience volunteering for a local shelter in socialization and vet transport, 3 years experience working for a doggy daycare and boarding facility, and I currently work part time for another local animal shelter. I am an experienced owner of dogs, cats, ferrets, chickens, guinea pigs, and more. I also have experience as a wedding dog handler, and would be happy to offer this service if requested so your furry companion can accompany you or someone you know on yours or their special day without any added stress, please let me know if this is something you'd be interested in! I currently work part time so I have lots of time to play with your pup, and hopefully can build savings towards a larger space to meet more people's needs! I am always looking to learn, grow, and provide better care for animals. Animal welfare is very important to me. At this point in time, due to the space I'm only able to accommodate smaller breeds that generally can get along with others. I do have a small fenced in yard, but I also have the bike trail and nearby hiking trails readily available, your dog will need to be on leash at all times when outside on walks/hikes, I do not provide "off-leash" trail experience as a safety precaution, thank you for your understanding! I am happy to provide pictures and updates of your pup whenever requested, please never be afraid to reach out!

Sitter Profile Image: Jessie L.
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Jessie L.
$39
total per visit
5.0 out of 5 stars
• 8 reviews
4 repeat clients
17 years of experience
Adams, MA, 01220

About: My name is Jess! Thank you for stopping by! ☺️ I’m 30 and work from home in Adams, MA. I have a fairly flexible schedule and am a classic Berkshire native. I have been a pet owner and lover my entire life! My boyfriend and I currently have two cats, Binx & Titan. Who are the loves of our lives. My family has always been pet lovers! We’ve recently lost our two havanese pups. We were pervious owners of a chocolate lab and a poodle mix. I’ve spent my life around different breads of dogs, big and small. As well as lots of cats! I will care for your pets just as you would and am happy to provide in home care in their own space to provide the best comfort. I am confident in handling all types of breds and needs of pets. I’ve been an experienced dog sitter for over 15 years! I started doing this when I was a teenager and never stopped. I love caring for animals. Please consider me for your pets next walk, meal, or sleepover! I currently work from home full time! I prefer to chat to see if the conditions work for both myself and the pets! Always open to questions/concerns/inquiries! My message box is always open. I prefer to care for pets just as you would! I love to understand their current routine and try to keep things as normal as possible for them to prevent anxieties.

Sitter Profile Image: Tara D.
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Tara D.
$30
total per visit
5.0 out of 5 stars
• 18 reviews
6 repeat clients
30 years of experience
Pittsfield, MA, 01201

“Tara did a wonderful job taking care of my skittish cat this weekend! She even deep-dived under my couch to look for him and ensure that he was safe, braving dust kitties and lots of toys! I plan on asking her to come back again, and I would definitely recommend her to care for furry loved ones. !”

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Donna C.
Sitter Profile Image: Leona O.
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Leona O.
$20
total per visit
4.8 out of 5 stars
• 13 reviews
3 repeat clients
10 years of experience
North Adams, MA, 01247

“Leona was great!! She took the time to sit with my dog and she was very patient with her. She gave great updates and you could tell she truly cared about my dog. Will be booking her again in the future.”

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Elizabeth B.
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: McKenna P.
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McKenna P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
• 412 reviews
153 repeat clients
8 years of experience
Lenox, MA, 01240

“It’s always reassuring to be able to count on McKenna. She has looked after our cat a few times. She always sends timely updates and takes great pictures!”

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Carolina J.
Sitter Profile Image: Kelsey R.
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Kelsey R.
$34
total per visit
5.0 out of 5 stars
• 72 reviews
31 repeat clients
12 years of experience
Pittsfield, MA, 01201

“Kelsey is great. I had to add another 2 days to the booking due to travel delays, and she was most gracious in helping out. She is there when I need her to take care of my kitties.”

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Betsy K.
Sitter Profile Image: James S.
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James S.
Star Sitter
$34
total per visit
5.0 out of 5 stars
• 16 reviews
2 repeat clients
10 years of experience
Williamstown, MA, 01267

“Bruno loved his visit and walk with James, who went above and beyond to check on Bruno's eating habits. Bruno can't wait for the next visit 🐕”

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Michael K.
Sitter Profile Image: Rita M.
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Rita M.
$28
total per visit
2 repeat clients
18 years of experience
North Adams, MA, 01247

About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently enrolled in college, as well as working various part time jobs so my availability is limited at the moment, but i will try my best to arrange my schedule best for yours ( and your furry friend’s) needs! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

Sitter Profile Image: Haley C.
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Haley C.
$34
total per visit
4 years of experience
Clarksburg, MA, 01247

About: I’ve taken care for more than a handful of animals before! I have worked for two farms in my life so far. I have also always grown up with having dogs, cats, and even hamsters and Guinea pigs! I am a mom of 2 little ones but just recently moved so I am in between jobs and can work with you on times! I am available most days and a good portion of the day, as the kids go to daycare! I am a very good listener and fast learner. I love following a guideline and care so much about your animals! I can’t wait to meet your pets!

Sitter Profile Image: Makenna C.
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Makenna C.
$17
total per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
22 years of experience
Bennington, VT, 05201

About: I have had dogs all my life and have taken care of my own since I am old enough now. I like spending time outdoors with my dogs and walking them and throwing the ball. I have plenty of experience as I have been on Rover for a few years now. I have about 4 pet families I sit for and I enjoy what I do! I work as a toddler teacher so my time varies throughout the week. I go into work at 8 and get out at 4. I have some week long breaks here and there. I am available most weekends. My dog takes meds right now for seizures so I am experienced at giving dogs medicine. Very responsible animal lover I have always had animals in my life. I am good about having the house clean when there’s a fluffy shedding dog in it. I have experience in cleaning up dirty crates, accidents on the floor and making sure the animal is being safe.

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: Logan S.
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Logan S.
$39
total per visit
5.0 out of 5 stars
• 31 reviews
13 repeat clients
25 years of experience
Rensselaer, NY, 12144

About: I've been taking care of a wide variety of animals for a long time. I have experience in all around basic boarding care for dogs, cats, and various reptiles and small animals; dog training basic obedience, fear or frustration aggression/reactivity, high drive dogs, and anxiety behaviors. Pet Care is not only an important part of my life, but it's a passion of mine. Caring for your animal like I do my own is what makes life rewarding for me. When your pet is with me it becomes a part of my family and is treated as such. I look forward to training or caring for your animals! I can train your dog in a multitude of ways. I work a lot of animals with anxiety and behavioral issues. I can easily crate your dog, cat or any other animal if needed. I have access to multiple fenced in yards for your pet to run around in and play. I have a fully trained purebred smooth collie who is extremely gentle and can make friends with anything. I have multiple rooms and spaces in order to accommodate your fur baby's needs. I pay attention to detail and carry out all care with the highest level of standards I can.

Sitter Profile Image: Michelle L.
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Michelle L.
$34
total per visit
20 years of experience
Niskayuna, NY, 12309

About: I am a pet owner and animal lover. I have experience caring for cats, dogs, horses, birds, fish, and rodents. I have worked with many animals and am comfortable grooming, walking, feeding, playing with and caring for your pets. I also have experience in medication administration I have been a volunteer at the SPCA and have participated in their pet care summer programs. I've spent most my life caring for all different types of animals and would love to help families out by doing the same for them. I am an energetic undergraduate student with a flexible schedule and look forward to meeting and loving your pets! Animals are truly a humans best friend. Please feel free to contact me to discuss my services. Yours truly, Michelle

Sitter Profile Image: Jeffrey S.
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Jeffrey S.
$62
total per visit
30 years of experience
Falls Village, CT, 06031

About: Hi I'm Jeff an experienced and professional pet sitter, dog walker, and provider of overnight pet care, I offer loving, dependable service that brings complete peace of mind. Whether it's daily visits or extended stays, your pets are treated like family every step of the way. I'm fully licensed, insured, and bonded, and certified in Dog and Cat First Aid & CPR—so you can rest easy knowing your furry companions are in safe, experienced, and genuinely caring hands. I have over 25 years of construction experience. I also offer Handyman Services which can be done while I am at your home. 🐾 Licensed, Insured, and Bonded • Certified in Dog & Cat First Aid and CPR Caring for animals isn't just something I do—it's my full-time profession, my livelihood, and my passion. I take great pride in providing dependable, compassionate care for pets of all kinds, including dogs, cats, birds, fish, chickens, goats, rabbits, hamsters, gerbils, and more. When you entrust me with the care of your beloved companions, I go far beyond basic walks and feeding routines. Their happiness, comfort, safety, and well-being are always my highest priorities. While I know I can never replace your presence, I work hard to provide the love, attention, companionship, and personalized care your pets deserve while you're away. To make life easier for my clients, I also offer handyman and home care services. Whether it's watering plants, bringing in mail, managing trash and recycling, hanging pictures, completing small repairs, painting, or helping with other household tasks, I'm happy to assist while caring for your pets and home. By combining professional pet care with reliable home services, my goal is to give you complete peace of mind, knowing your pets are loved, your home is cared for, and everything is being looked after by someone who genuinely cares. 🐾❤️🏡 When you entrust me with the care of your furry companions, I go above and beyond basic dog walking and playtime; I prioritize their happiness and welfare. Understanding that I can never replace your presence, I tirelessly strive to complement your affection and care by providing the attention and love your pets deserve, even in your absence. I also integrated handyman services into my offerings, recognizing the convenience and practicality of addressing tasks while caring for your pets. Whether it's watering your plants, hanging a picture, managing waste or recycling, or even handling small repairs and painting, I am here to help. Through this fusion of pet care and handyman services, my aim is to simplify your life while ensuring the well-being of your cherished pets and your home.

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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.

How to book pet sitting

  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 - Cheshire

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FAQs for Pet Sitting - Cheshire

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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