Cat Sitting Winchester
Book a cat sitter to stop by your home to feed and play with your cat.
Winchester, Find top rated cat sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Susan was wonderful with my cats, and I would highly recommend her to anyone looking for a caring and attentive pet sitter. From the start, you could tell she genuinely cares deeply about animals. She asked thoughtful questions, paid close attention to detail, and ensured my cats received the best possible care. She was also very personable and kept me updated while I was away, which gave me a lot of peace of mind. I've already rebooked her to pet-sit for me again! She’s the best.”
“Amie is a true pet care professional! Our cat, who doesn’t like everybody, instantly connected with the Amie and her bonding skills. We came home to a happy and healthy cat. We pet parents are very happy.”
“Ayden was a fantastic house sitter. He took incredible care of our numerous animals, and even noticed that our pellet stove had malfunctioned and let us know! We highly recommend him.”
“Haley was excellent! Very responsive and took great care of our two kitties. She is a genuine animal person and provided really thoughtful updates (which eases anxiety while away from the fur babies). Will absolutely use her again in the future!”
“Kiersten did a wonderful job caring for our cats while we were away. She followed our instructions, and our cats were relaxed and well fed. One of our cats has been sick and she gave him his medicines, and he is looking even healthier than when we left!”
“Maggie provided excellent cat care and house sitting. I appreciated that she fit us in last minute and accommodated our schedule around some other commitments she had. I would definitely book her again!”
“Nadine was Fantastic, it took a few visits for our Cats to warm up to her, she kept the kids Litter box’s clean, and food bowls Filled, also Vacuum around their Litter Boxes, so their area was always Clean, the Bangel Brothers love her time spent playing with them! We are Extremely happy with Nadine, and will Definitely use her Services again when we travel out of town!”
“Do your pets a huge favor and let them be cared for by Michelle….what a wonderful pet sitter…. Plenty of attention and body rubs and scrubs !!! Our pets were so blessed to have Michelle as their temporary mama !”
About: I have taken care of cats, dogs, Small animals like mice, guinea pigs, fish, turtles. All way to farm animals like sheep, goats and even horses. Due to growing up in small town farming community. Currently I am supervising and helping my teenage daughter care for multiple miniature and full size horses in Leverett MA. I also have two wonderfully spoiled cats and a dog at home. Have some openings in evening and most weekends as at this time I do have a full time 9-5 job. Looking to see where this goes. I do not have fenced in yard but I keep my current dog on tie out or 50ft lead. Very quiet not normally traveled area around house with big yard to play. At clients home depends on environment there. Would prefer no off leash unless securely fenced area.
“Kendra did drop in visits for my two cats for a week. She was patient, affectionate, and attentive to gaining the trust of my timid cat and stimulating my frisky cat. She expertly administered medicine as scheduled for my cat that required it. She maintained a clean living space, frequently scooping litterboxes and washing food and water dishes. I felt completely at ease from her updates, and when I returned home my kitties seemed at ease as well. She is a knowledgeable, professional, compassionate petsitter. 10/10 would recommend.”
“Elias took fantastic care of my tricky kitty, including administering meds in food and dealing with frozen wet food (Smalls) which is trickier than scooping dry food or opening a can. They were very responsive communication-wise and enthusiastic. I will definitely turn to them again for kitty care when I next leave town.”
About: Experienced in caring for puppies, kittens, and senior pets. I provide walks, playtime, and can manage medications or special diets. I treat every pet like a cherished member of the family, ensuring they feel happy, safe, and loved while you’re away. My schedule is flexible during weekdays, which allows me to provide reliable walks, drop-ins, and pet care throughout the day. I work part time, so I’m able to accommodate many daytime and evening requests with advance notice. I make sure pets feel safe, comfortable, and cared for while keeping their normal routine consistent. I provide feeding, walks, playtime, fresh water, and lots of attention, while also keeping owners updated with pictures and messages. I’m respectful of clients’ homes and always make sure pets are happy and well cared for.
About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.
About: I have over 10 years of pet care experience including walks, overnight stays, and short visits. I also grew up with dogs and have lived with a few different cats in my adult life. I am new to the Rover app but am happy to provide references upon request. I work Monday-Friday 11-5 in Brattleboro. I can do overnights any day of the week, but just know that on these days I will be away for 6-7 hours depending on distance from your house. I love taking dogs on long walks and can do so 2-3 times a day. I am super communicative and experienced at house sitting while pet sitting. I am very respectful of people's homes and pets' routines. I will make sure to keep your house as clean - and your pet as happy - as you left them.
“Emily spent a month with our cat Yoyo (Yosemite Sam) while we were away. They became pals. Emily took good care of Yoyo and sent us a photo of him every day. Emily also babysat our indoor and outdoor plants, especially some special ones that we had just planted before our trip. They in great condition. We definitely recommend Emily as a pet sitter and hope she will be available the next time we go away.”
About: Ive been caring for pets for many years. I had a dog walking business over a decade ago. We taken care of our own and others elderly dogs. We like taking dogs on long off leash walks in groups if possible. Dogs are always welcome to cuddle up on the furniture. Im a stay at home-mom, homeschooling. We go to play groups and trips but we can plan our day around dog walks. We take the dogs out first thing in the morning on leash as our yard isnt fenced. We are happy to come feed kitties and water plants. We love taking dogs out on walks and caring for them in our home. We love going on long walks mid day out in nature
“Lori’s service, taking care of my elderly cat, was remarkable. It became clear quite quickly that she was thinking of my cat’s welfare first and foremost. I’m inexperienced with having cat sitters staying the night in a house sitting capacity. Lori handled my cat’s needs as well as my general requests expertly - and I felt reassured. She exceeded my expectations, showing consideration by offering to do a task or two I hadn’t requested. All in all, she was lovely to work with. With Lori caring for my cat, I feel confident taking longer trips, knowing my cat will be so well looked after!”
About: I tend to be fun, responsible, and calming for them. I like it and take pride in it. The best thing about caring for animals, is seeing their personalities, what they consider manners, and seeing them light up when they're being respected on their terms too. The best part of my mornings on my family farm, is taking a hike with the Bassett. Neither of us are satisfied with our morning until it happens. She needs it, and deserves it. While I'm away from her, I need to hike, or I get soft I ask owners what their pets needs and personalities are. What they consider manners, and if they are tricksters, what to expect. All animals are their own kind of person, and they deserve to be treated as such.
About: I have been taking care of animals for as long as I can remember. Walking, feeding, and bathing both dogs and cats. I consider my pets family members! All of my babies are rescues. I have trained my dog through the GoodPup app and he knows the commands sit, stay, lay down, up, paw, leave it, heal, touch, and find it. All my pets are given enrichment activities throughout the day. They’re also stimulated with play/exercise. I know dog and cat body language. I have worked with dogs that have seizure disorders and know how to administer medication to both cats and dogs. I’m work Monday to Friday with my weekends free and open. My work schedule is Monday-Friday 8:30am to 4:30pm. I can take dogs for long walks, stimulate them through play, or with enrichment activities. I can administer medication if needed. For cats I can clean the litter box and stimulate them through play or enrichment activities. I can administer medication if needed. Pet safety is my first priority. I believe knowing pet body language is so important because that’s how they communicate their needs. I will care for your love ones as if they were my own! I will follow your schedule and instructions exactly as is because, you know your pet best! I can bath, walk, feed, administer medication, and give my full attention to your babies ☺️
The median cost per visit for cat sitting in Winchester is $25
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?
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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 cats like family
1. Search
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Popular requests for cat sitting - Winchester
Select a filter and find qualifying sitters offering cat sitting.Sitters in Winchester average 6 repeat cat sitting clients
FAQs for Cat Sitting - Winchester
Frequently asked questions about Rover
As of September 2026, there are 230 sitters on Rover offering Cat Sitting across Winchester. 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 Winchester. On Rover:
- 88% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 94% 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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