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 did a great job taking care of our 100 lb Maremma. She was on time for all the sessions, and spent plenty of time with our dog. Our dog really liked seeing her. We will definitely be using her again.”
“Amie was a rockstar! She was very thorough and asked appropriate questions to ensure the best possible care for my cat. She is knowledgeable, has excellent communication, and provided detailed updates. She was incredibly kind and patient with my anxious kitty, and I am so grateful to her!”
“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 is a natural with animals. She’s calm and confident around them and people too. Our Merry can be shy but she was fine with Maggie right away. Maggie is polite, presents herself well, and always on time, with a good attitude! We will use her again.”
“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 once again did an amazing job taking care of our two cats while we were gone for over a week. They were immediately comfortable with her on the first visit. She sends thorough updates and photos every visit showing them playing and interacting with her. I highly recommend her services. She's very reliable and communicative, and is a great fit even for skittish kitties. It was such a relief to know that she was checking in on our cats while we were gone!”
“We’ve had Amber drop in on a few separate occasions now and have had a great experience each time. She’s been attentive to both dogs behaviors and makes sure to check in with questions or concerns. I have a peace of mind when Amber visits if I’ll be away from home for an extended time during the day. Based on the photos, the dogs definitely have a great time with her too!”
“Emily was amazing with Pepper, my shy hound. Emily showed up promptly for each visit and was very thorough. Even her pre-visit questions were thorough. She is very caring and kept me very informed. I highly recommend Emily.”
“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.”
“Kendra took excellent care of our two kitties while we were away! I was amazed by the level of thoroughness checking on each one and how they warmed up to her. Cats were very well taken care of and the pet areas clean when we returned home. The daily updates with pictures of our kitties was a huge comfort... Looking forward to having Kendra watch our kitties again in the future!”
“Nadine did an amazing job with our cat. Lots of playtime and pets when she stopped by for an evening drop-in. She kindly sent videos and pictures too! We hope to use Nadine again in the future!”
“Lori was great with my two older dogs. I travel a bit and my schedule is really complicated, which Lori handled really well. I have already booked her for a future travel date. Great job Lori”
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 ☺️
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.
“Ria was an amazing sitter for us when we left for an international trip for our cat Lily. She takes so many adorable photos and videos that we loved watching while we were away. She was incredibly descriptive with her check-ins and was great with Lily and making sure she checked with us about her feeding habits etc to make sure what was normal for her. We’re so lucky to have found her as we just recently moved to the area and needed a new cat sitter- thanks so much Ria!”
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.
About: I’ve had pets since I was about 4 years old, and am experienced with caring for cats and dogs. Any needs they have, I will take care of them all - from simple company when you're at work, to walks, giving meds and overnight stays! I have experience training puppies too, from potty training to the classic "stay", "sit", "come", "leave" etc. commands. I have a large dog myself so size of your pet is no issue. Anything you're unsure about, shoot me a message! I work full time at a school but am free weekdays after 2pm until around 10pm. On weekends I am free from Friday afternoon until Monday morning so I can do overnight stays too if needed. Depending on the care required, I will feed pets, give them meds, take them outside, play games/fetch/etc., brush them, empty litter boxes and so on. I have had several cats and dogs of my own and cared for many more, so I am comfortable with adjusting to their different personality types.
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
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
Browse profiles of sitters near you who offer cat sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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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 Drop-In Visits - 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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