Cat Sitting Cheshire

Book a cat sitter to stop by your home to feed and play with your cat.

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Cheshire, Find top rated cat sitting

Prices are estimates per visit for 1 cat. 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
$16
total per visit
5.0 out of 5 stars
33 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
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 in animal shelters and a local doggy daycare, 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 on your special day without any added stress. 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: Alyson V.
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Alyson V.
Star Sitter
$23
total per visit
5.0 out of 5 stars
26 reviews
14 repeat clients
11 years of experience
Dalton, MA, 01226

Alyson was great with communication and (luckily) able to accommodate our last minute booking, coming next day for a meet and greet. I instantly felt comfortable with her, it was obvious that she loves animals, and I had no worries that the animals would be well taken care of while we were away. Came back to happy creatures and I am sending another booking request shortly! Thanks Alyson!

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Rose S.
Sitter Profile Image: Tara D.
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Tara D.
Star Sitter
$27
total per visit
5.0 out of 5 stars
6 reviews
2 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: paige a.
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paige a.
$19
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
28 years of experience
Adams, MA, 01220

Paige took great care of our cats! She was very communicative and took pictures of our cats during the visits. She also left great updates during her visits and made me feel like she was keeping good tabs over the days. I look forward to having Paige watch our cats in the future!

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Lucas N.
Sitter Profile Image: Lindsey S.
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Lindsey S.
$12
total per visit
5.0 out of 5 stars
1 review
25 years of experience
Cheshire, MA, 01225

About: I've grown up with dogs & cats. I am very involved in rescuing & fostering & have plenty of experience with all sizes, ages, temperaments & am experienced with most medical issues/medicating regimens. My schedule for work is Monday- Friday 7:30-4 pm. I'm available from 5-10 pm weekdays for drop ins and walks. I have open availability for weekends to house sit, go on walks and do drop in visits. I am currently in the process of relocating to New Hampshire permanently. I work full time Monday through Friday and offer pet care on evenings during the weekday, and full time on weekends :) I'm experienced with providing care for difficult dogs and cats and have no issues being able to give medications.

Sitter Profile Image: Caitlin H.
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Caitlin H.
$26
total per visit
5.0 out of 5 stars
17 reviews
3 repeat clients
4 years of experience
Pittsfield, MA, 01201

Took good care of our fog

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Scott B.
Sitter Profile Image: Danielle P.
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Danielle P.
$16
total per visit
5.0 out of 5 stars
17 reviews
6 repeat clients
44 years of experience
Adams, MA, 01220

Thanks so much for what you do for Victoria and so many other animals Danielle. You are an angel.

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Robert S.
Sitter Profile Image: Trista S.
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Trista S.
$16
total per visit
5.0 out of 5 stars
19 reviews
6 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: Michelle T.
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Michelle T.
$16
total per visit
20 years of experience
Pittsfield, MA, 01201

About: I have prior pet sitting experience and it's something I genuinely love doing. I'm comfortable with feeding, walking, playtime, giving attention, and keeping pets on their normal routines. My 20 years of experience has taught me the importance of patience, reliability, attentiveness, and building trust with both pets and owners. I understand how important it is for families to feel comfortable leaving their pets in someone else's care. I always make sure pets are safe, loved, and well cared for. I am an educator so I have summer time flexibility. During the school year, I am available before and after school hours, evenings, weekends, holidays, and school breaks. In the summer months, I have full availability and plenty of time to dedicate to pet sitting, walks, visits, and providing attentive care. My schedule allows me to be dependable, consistent, and flexible for pet owners' needs. When caring for pets in a client's home, I do my best to keep their normal routine consistent so they feel comfortable and secure while their owners are away. I make sure they are fed on schedule, have fresh water, receive exercise, and get plenty of attention and affection. I also keep the home tidy by cleaning litter boxes, picking up after pets, and making sure everything stays safe and organized. I pay close attention to each pet's personality and needs, whether they enjoy lots of interaction or prefer a calmer approach. My goal is always to provide loving, dependable care while helping pets feel relaxed in their familiar environment.

Sitter Profile Image: Iris F.
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Iris F.
$16
total per visit
4.9 out of 5 stars
54 reviews
12 repeat clients
10 years of experience
North Adams, MA, 01247

Iris was amazing! I went on a last minute vaca and contacted iris, she was very communicative, and even sent me pics of my kitties when she went over. Iris not only fed my cats, but she spent time with them. Iris cleaned thier litter box and even swept up the litter. Next time I go away I'm choosing Iris awesome job and thank you!!!

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Douglas P.
Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$34
total per visit
5.0 out of 5 stars
383 reviews
149 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna was amazing with our 2 cats, Pepper and Maggie. She was very reliable and easy to contact. We would definitely use her services again. We can't thank you enough!

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Alice P.
Sitter Profile Image: Reymon B.
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Reymon B.
$20
total per visit
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

Sitter Profile Image: Aubrey H.
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Aubrey H.
$29
total per visit
5.0 out of 5 stars
11 reviews
8 repeat clients
21 years of experience
North Adams, MA, 01247

Aubrey took great care of my 3 cats while I was away for a week. I'll certainly turn to her first the next time I need some catsitting.

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Emily B.
Sitter Profile Image: Leona O.
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Leona O.
$19
total per visit
4.7 out of 5 stars
6 reviews
10 years of experience
North Adams, MA, 01247

About: I’ve taken care of dog of many sizes and health conditions, I have had a cat for 9ish years and have cared for friend and families dogs for years. I am a student, I am relatively free but lots of work to do! I like to go on walks already! I am able to be flexible. I know how to feed animals and care for them, can follow special instructions as I know they are important. As much as I would love to care for your fur baby at my home, I cannot.

Sitter Profile Image: Maura A.
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Maura A.
$40
total per visit
5.0 out of 5 stars
3 reviews
30 years of experience
Adams, MA, 01220

About: Hi! I’m Maura, a high school English teacher who has lived and worked in the Berkshires for 19 years. I’ve spent my entire life caring for animals of all kinds, and my goal is simple: to provide safe, personalized care so you can enjoy your time away without worrying about your pets. I offer dog walking, drop-in visits, house sitting, overnight pet care, and small farm sitting throughout the Berkshires. Whether you need someone to check on a new puppy, care for a senior pet, or manage a small farm while you’re away, I’d love to help. I have experience caring for dogs, cats, rabbits, ferrets, hamsters, gerbils, rats, large aquariums, horses, cows, goats, and pigs. In addition to caring for my own animals, I have experience managing an equine boarding facility with 19 horses on the property and am comfortable handling a variety of animal personalities, energy levels, and care needs. I am experienced with: • Puppies and kittens • Senior pets • Oral medication administration • Basic trick training and potty training • High-energy dogs • Shy or anxious animals • Horses and livestock requiring daily care routines I also offer red light therapy sessions for pets, both small and large, upon request. Coming soon: private in-home boarding! I am currently creating a private pet guest house on my property that opens directly into a fully fenced backyard. My goal is to provide a low-stress alternative to traditional kennels by boarding only one pet family at a time. This allows your pets to receive individualized attention in a quiet, secure environment without the stress of sharing space with unfamiliar animals. If this is something you’d be interested in, feel free to reach out for details. I know firsthand how stressful it can be to leave beloved pets behind when traveling. That’s why I prioritize communication, reliability, and personalized care. I provide regular photo updates and am always happy to check in while you’re away so you can feel confident that your pets are safe, comfortable, and well cared for. Whether you’re visiting the Berkshires for a weekend, heading out for a day of skiing or sightseeing, or leaving town for a longer trip, I’d love the opportunity to care for your pets as if they were my own. Please feel free to reach out with any questions about services, availability, or your pet’s specific needs. I look forward to meeting you and your animals! I’m always running errands for my pets, spending time with my pets, or I’m at the barn with my horse. Taking care of the needs of my own pets is one of my top priorities, and I can easily work your furry friend into my schedule! It’s important that we discuss your specific expectations and needs as a pet owner/parent to ensure that you get the best care! Every pet owner and pet is different and I want to tailor my approach to what your pet is used to and comfortable with.

Sitter Profile Image: Bella G.
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Bella G.
$20
total per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
10 years of experience
lanesborough, MA, 01237

I can’t recommend Bella enough! From the moment I met her, I knew my pups were in great hands. She took the time to get to know my dogs and their routines, which made me feel so at ease. Throughout my time away, Bella sent me daily updates and adorable photos of my pups playing and enjoying their time. Each picture captured their happiness—tails wagging and big smiles! It was such a relief to see them so content and well cared for. She truly went above and beyond, providing not just care but also love and attention. I will definitely be booking Bella again for future trips. If you’re looking for someone reliable and caring, look no further!

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Bonnie V.
Sitter Profile Image: Laci M.
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Laci M.
$26
total per visit
5 years of experience
Dalton, MA, 01226

About: I’ve taken care of cats and dogs for about five years now and I have a lot of experience. I’ve worked anywhere from doggy daycare‘s to overnights to boarding dogs in my own home. I’ve always considered myself an animal person and I just love to care for them. I’m currently in cosmetology school so Monday through Friday, I’m in School from 9 o’clock until 430. After that, I plan to stay where I’m dog sitting for so that they get the most love and attention when I am able to be there. I really like to take it on the owners terms. I always prefer to meet the animal I’m caring for first however, if that’s not possible then it’s totally fine, however I like to listen to what the animal tells me, what boundaries it’s giving me, but I love to be able to play with them take them outside as much as possible feed them when necessary and give extra treats because they’re such good babies. I just appreciate the owners letting me know what they do and don’t want from me as a host.

Sitter Profile Image: Jessie L.
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Jessie L.
$36
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: Dana G.
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Dana G.
$30
total per visit
5.0 out of 5 stars
40 reviews
11 repeat clients
20 years of experience
PITTSFIELD, MA, 01201

About: I've taken care of animals since I was a young child. I have always felt love and responsibility to our animal friends. I worked with cats, dogs, reptiles, birds, horses, guinea pigs, and rabbits. I want to fill my days with helping wonderful pet parents provide the attention and care their pets deserve. I have multiple dog walks daily and will make sure your pet gets lots of love too. I am able to stay away from home for periods of time while my family helps care for my animals and home. I have 2 separate unoccupied bedrooms to allow for private space for animals. I live across from springside park and have a mostly fenced yard with leads. I'm dedicated to pet care. I have daily walks generally in the mid-afternoon. I have online meetings Wednesday and Saturday which I can attend in your home, mine or anywhere with internet access. I have separate spaces available for each animal in my care at any time. I will use provided equipment for transportation. Your pets safety is number one.

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The median cost per visit for cat sitting in Cheshire is $25

Cat parents share their Rover experiences - Cheshire

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5.0 out of 5 stars

Morgan was very kind and understanding when it came to my cat, Finlay, and was very good at keeping me informed. Finlay isn't good with strangers at all and hid the entire time. However, Morgan's updates on Finlay's eating/drinking reassured me that she was doing ok. I'm so thankful for Morgan and will definitely go through her again.

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Erin S.
Drop-In Visits
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Sitters in Cheshire average 7
repeat cat sitting clients

FAQs for Drop-In Visits - Cheshire

Frequently asked questions about Rover

As of July 2026, there are 364 sitters on Rover offering Cat Sitting across Cheshire. Enter your ZIP code to see which available sitters are closest to your home.

Cat sitters on Rover care for your cats’ needs and can spend quality time with them, including activities like feeding, playing, and refreshing their water and litter boxes. Depending on your arrangement, you can schedule as many visits per day as your cat needs or find a sitter who can stay at your house overnight. Some sitters also board cats in their home.

House sitting can be ideal for cats who need socialization or care that lasts longer than a few hours. Your cat stays in their own home, on their own schedule, with care based on what you and your sitter agree on together.

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.

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

Yes, you can find sitters who have experience with handling special pet needs in Cheshire. On Rover:

  • 94% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 98% 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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