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

Over 159 pet parents in Winchester have booked cat sitting
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.
“Kimberly is absolutely awesome!! She came by the day before she was contracted just to meet my dog and go over any special needs or requests. Kimberly is genuinely a kind, sweet, caring person. I feel so comfortable having her take care of my Lulu. Her communication is so good. Sent pictures as well as messages about her visit and what all Lulu did. My new favorite person for Lulu!!❤️❤️”

“I am very happy with Christa! She did an amazing job with my pups. Bo and Sheena are very happy too. This was my first time using this service and I’m so happy that I found Christa. It’s not easy for me to leave my pups with anyone. Thank you Christa for being so kind and friendly to my pups. I will definitely be using these services again and request for Christa.”


About: I work full time at Shenandoah University and am joining Rover to formalize my side hustle, which Ive largely managed through word of mouth thus far. I’ve lived with dogs for about 25 of my 30 years of life - mostly hounds (most recently 2 bassets). And I’ve watched dogs of all sizes, the smallest being a chihuahua mix and the largest a Great Dane. Over the last 5 years or so, I’ve dog sat for friends, family, and connections in the Winchester area. The longest engagement was 6 weeks, but I normally do long weekends or week long jobs. All animals are different and I respect you, their owner, to tell me what’s best for your furry friend. I also will be transparent and over communicate with you so we both can be confident your animals have everything they need. I’m comfortable dispensing medication - including to the really picky ones (I can take a pill/pill pocket and sculpt it pretty much exactly the same shape and size as any mainstream kibble brand). I have experience with puppies and with our senior citizens, who both just need a little extra care and attention. I feel comfortable listening to animals and getting to know their personalities, which are all so different yet equally endearing. If they are trying to say something, though, I feel pretty confident I will notice it - especially after we’ve spent a few hours together. And, if they’re trying to say something and I don’t understand? I’ll reach out just to make sure. I just really, really love animals. I most often watch dogs but have also cared for cats, lizards, bunnies, chickens, and horses (although horses were largely just feeding and brushing/attention). I also have a rescue cat of my own, Luna, who has made me certain I’m equally a dog person AND a cat person. I work 9-5 M-F, and occasionally am tied up on weekends with happenings on campus. I can take an hour lunch (and flex a bit beyond if necessary) to visit the animals for attention and potty breaks. I am single, sober, and genuinely grateful for the work and the company. Animals have so much love to give, and i try to reciprocate that love indiscriminately. Thanks for your consideration and please let me know if I can answer any questions, hop on a zoom call, or speak to any specific needs you find important. No request is too small and I’m grateful for any and all details I can use to keep your animals feeling secure, loved, and cared for in your absence. I work full time at Shenandoah University as an Administrative Assistant in the Office of Global Engagement. My role is in-person on the main campus in Winchester. My routine hours are 9-5 with an hour lunch around 12 or 1. But, there’s a lot of flexibility, especially over the summer when the students are back home. My team is small and I am able to shift my hours when I communicate with them in advance (I.e. I’ll take 2 hours midday but clock in at 8, etc). Outside of work, my schedule largely centers around community and service work. I’m really involved with the recovery community and attend several meetings and events a week, although I can be flexible there too. Most days I’m up no later than 7 am and asleep by 11. But all these things can flex, depending on your and your pets needs. I live alone with a stray-turned-adopted cat named Luna. My place has a small fenced area in the back, enough room for a pup to potty but not much more. But I’m also about a half a mile from Jim Barnett Park and I love their walking trails and their dog park. I’d prefer to house sit at your house, but I’m open to certain scenarios if I can ensure your animal is comfortable in my space. Let’s talk about the details!
“Courtney was excellent with our 2 cats. Our shy boy warmed up to her very quickly, which is rare. She also took great care of our elderly girl, including giving insulin injections. We look forward to booking with her again next time we go out of town.”

“Matt was fantastic! We had to extend our trip and he was flexible with us. Spent a good amount of time for drop in visits and sent photos of happy pups! Thank you Matt for taking care of our pups while we traveled. Will definitely rebook with Matt as needed.”

“Alexsys did an amazing job with my dog. She cared for her like she was her own and sent me plenty of updates. My dog was happy and well loved while we were out of town. Will definitely be booking with her in the future!”

“Gabby took excellent care of our animals while we had to go out of state. I could tell from her pictures and from how they were acting when we got home that they really enjoyed their time with her. We'd absolutely book Gabby again in the future!”

“Totally worthy of 5 stars! Hannah was awesome and Jake really loved her visits. You can tell she really cares about her work and the animals she visits. Highly recommend!”

“Angelina was fantastic! She took great care of my kitty while I was away and sent regular, detailed updates and pictures. Definitely provided a lot of peace of mind knowing my cat was in good hands.”

“Charlotte is very knowledgeable and reliable. She took good care of my cats while we were out of town. I will book her again and highly recommend Charlotte for pet sitting services.”

“Megan did great! Thank you so much for being there for our girl on our special day. We felt so much better leaving her at home knowing she would have someone come check in on her.”

About: We provide a special touch of walks, wags and worry free pet sitting! From zoomies to cuddles we can match your fur babies energy level. Apple Pay,Venmo,Cash or in app payments welcome. We’re a meticulously organized couple which permits us a flexible schedule when caring for our fur babies. We’d love to extend the care to your fur babies as well! We recognize that each pet has their distinct personality and we like to honor that. Pelusa, our oldest cat, despite her age, carries a playful kitten soul so we like to dedicate extra stimulating play for her. Our youngest he likes to exert his energy by bird watching and running and jumping around so we’ve accommodated the house for his races since playing 1 on 1 with him does not captivate his curiosity. Just like that we can confidently say we love learning about our clients and their pets personality so we can make the best transition when caring for them that day and so everyone feels seen and included, even the little ones! We also understand pets can be very oriented to habits so we like to know what habits and/or rules you have for your pets so we can respect and abide to those as well!

About: I have had dogs my whole life and I have had a cat for the last 7 years. I am very good with animals and I love them very much. I have also babysat my own dogs when my parents go away as well as my aunts cats, and my neighbors dogs and cats. Since I've had many animals in my life, I know how to take care of them and I know how to tell what they need. I am in college but have many hours throughout the days that I am available and I am also free most nights (though I would need notice incase I make plans with friends) I am available all day on Mondays, available from 11-2 and after 5:30 on Tuesdays and Thursdays and available all day besides 2-4 on Wednesdays and Fridays. I am also available all day on weekends I would just need to know in advance due to plans. I will offer your pet lots of love and will do whatever is best for your pet! I can easily crate your dog and I love long walks and would be happy to go on one with your pet.
“Was nervous about trusting a stranger to care for our pets but Mariah was absolutely amazing with communication, meet and greet, and took great care of our cats. Will definitely use her again!”

“Melissa was such a lifesaver! She helped us super last minute when a previous sitter fell through right before we left for a family reunion, and we couldn’t be more grateful she was there! Super flexible and communicative, Melissa took lots of adorable pictures and left detailed updates of each visit. And she was super sweet with our fur babies and loved on them so much! 100/10, will absolutely recommend and hire for her again! Thank you so so much Melissa!”

The median cost per visit for cat sitting in Winchester is $20
Cat parents share their Rover experiences - Winchester
Lauren was excellent! We initially did a meet and greet and I felt very comfortable with her. She ended up watching our cat for a week while we were away on vacation. She did a great job! She checked in with me every day and provided pictures and feedback. I will be using Lauren in the future anytime I need pet sitting.

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.
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
It's that easy! All payments are processed through Rover's secured platform
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
The average cost for Cat Sitting in Winchester on Rover is $25.53 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 Cat 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 Cat Sitting. For more information on service fees, click here .
As of August 2026, there are 405 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:
- 93% of sitters can help with special care needs
- 99% 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.
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.








