Cat Sitting in Winchester

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

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Top rated Winchester cat sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Karen O.
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Karen O.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
19 reviews
9 repeat clients
12 years of experience
Winchester, VA, 22602

Karen was great! We had a trip planned and Whiskey had been sick since November. Thought he would get better but still had a lingeri g cough. We had another sitter lined up who had their own dog and we didn't want that dog to get sick too. I found Karen last minute to come to our home and take care of Whiskey with dropins. She did such a great job and kept us informed on his coughing. Thank you so much!

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Michelle R.
Sitter Profile Image: courtney b.
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courtney b.
from
$17
per visit
5.0 out of 5 stars
46 reviews
14 repeat clients
20 years of experience
Winchester, VA, 22601

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.

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Noah Z.
Sitter Profile Image: Hailey C.
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Hailey C.
from
$13
per visit
10 years of experience
Winchester, VA, 22602

About: I have been a pet owner for as long as I can remember. I have had both dogs and cats and love them both equally. I have cared for pets for both family members and friends. I've watched all types of animals with many different personalities. On top of pet sitting, I have fostered multiple litters of kittens, which has taught me patience and attentiveness. In my free time, I also enjoy volunteering at a local rescue to help walk dogs. I understand the hard work, attention and love that goes into managing any kind of animal, and I am willing to do just about anything to make sure that your pet feels loved and safe. I am a grad student who only has in person classes on Tuesday typically 8am - 4pm, which makes me very flexible for the rest of the week. I am very conscious about safety when it comes to walk, and/or letting dogs out in a fenced in area. I am sure to read any instructions before hand to learn about any issues individual pet needs.

Sitter Profile Image: Samantha H.
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Samantha H.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

About: Hello! My name is Samantha. I have grown up with all sorts of animals including dogs, cats, rats, lizards, snakes, ect. I have dog sat in the past for friends and family and have raised/helped raise several different dog breeds including a litter of 9 Doberman/cane corso puppies. I love animals and give them all the attention and care i can offer! I am not currently working, so i have a lot of free time on my hands, especially during the week to fill with animal love! I will treat your house as my own and respect your space. I will clean up any mess left from your pooch if any and follow whatever directions you leave for me

Sitter Profile Image: Kimberly B.
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Kimberly B.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
318 reviews
111 repeat clients
8 years of experience
Winchester, VA, 22601

I simply cannot say enough about what a wonderful caregiver Kim was while my family and I left town recently. She sent daily updates with pictures that allowed us to see how well our kitty was doing. She cleaned up the area and kept him entertained and fed. Her loving demeanor also ensured he was calm and free of anxiety. We have found our “go to” caregiver from this point forward. She is absolutely wonderful!

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Jennifer M.
Sitter Profile Image: Hannah D.
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Hannah D.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
82 reviews
19 repeat clients
10 years of experience
Winchester, VA, 22602

She was very reliable and detailed with what she did for our kitties. She sent photos of the food bowl before refilling so that we knew how much our cat was eating. Would definitely recommend!

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Jamie S.
Sitter Profile Image: Alyssa F.
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Alyssa F.
from
$20
per visit
5.0 out of 5 stars
71 reviews
10 repeat clients
7 years of experience
Winchester, VA, 22601

Alyssa is so amazing with the pups, and I'm very grateful for her professionalism.

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Christian G.
Sitter Profile Image: Gabby T.
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Gabby T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
138 reviews
28 repeat clients
5 years of experience
clearbrook, VA, 22624

Gabby gave live updates and took lots of photos of our babies. Great communicator and you can tell our pups enjoyed her company with the report card photos. Thanks again!

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Erika D.
Sitter Profile Image: Alexsys T.
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Alexsys T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
304 reviews
118 repeat clients
7 years of experience
Clear Brook, VA, 22624

Alexsys did a great job with our 3 dogs and 4 cats while doing drop-in visits to our home. The communication was great and she was very prompt and kept to the agreed upon time. I would recommend her and will definitely book with her again. Also, she deserves a huge kudos to being available for the last minute (2 day) notice about booking

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Jamie E.
Sitter Profile Image: Lisette R.
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Lisette R.
from
$16
per visit
5.0 out of 5 stars
78 reviews
32 repeat clients
6 years of experience
Winchester, VA, 22601

She did an excellent job with my two cats! I can tell they were well taken care of and were just as happy as I left them! No messes either, which was a first!

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Cooper B.
Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Winchester, VA, 22601

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.

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Susan T.
Sitter Profile Image: Sophia M.
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Sophia M.
from
$16
per visit
5 years of experience
Winchester, VA, 22601

About: Animals have always been a huge part of my life. I currently have 4 cats and a 4-month-old puppy, so I understand the patience, attention, and love pets need every single day. Growing up surrounded by animals taught me how to care for pets with different personalities, energy levels, and needs. From playful puppies to independent cats, I’m comfortable handling feeding schedules, walks, playtime, cleanup, and giving pets lots of affection and attention. I treat every pet like family and always make sure they feel safe, loved, and comfortable while their owners are away. I currently work a flexible part-time job, which gives me plenty of time throughout the week to care for pets and give them the attention they deserve. Since I also have 4 cats and a 4-month-old puppy of my own, pet care is already a big part of my daily routine. Caring for animals comes naturally to me, and I enjoy spending my free time with them. I make sure every pet feels safe, comfortable, and cared for whether I’m in my home or a client’s home. I pay close attention to each pet’s personality and needs, whether they’re energetic, shy, young, or older. In a client’s home, I always follow instructions carefully to keep pets on their normal routine and help them feel as stress-free and comfortable as possible while their owner is away.

Sitter Profile Image: Kathy G.
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Kathy G.
from
$20
per visit
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

Kathy was so responsive and reliable! She took great care of our dog and gave detailed info as well as pictures after all of her visits! we will definitely use her again ☺️

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Meredith C.
Sitter Profile Image: Suellen W.
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Suellen W.
from
$18
per visit
2 years of experience
Winchester, VA, 22601

About: I’ve had dogs my entire life, and got into dog training 2 years ago. I assisted a dog training company with the dogs they would board and care for, and assisted with multiple training outings. I also raised and trained my own service animal. I’m currently working part time, and will focus solely on providing care for your pet and home. They are my number one priority and love to do things with them. I will take them on long walks and do training with them to get their brain going. I’ll make sure their meals are extra tasty and made with love.

Sitter Profile Image: Christopher P.
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Christopher P.
from
$25
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
13 years of experience
Winchester, VA, 22601

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!

Sitter Profile Image: Alex M.
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Alex M.
from
$14
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
Winchester, VA, 22601

Alex was great while dropping in on my dogs. She went above and beyond what was asked and the pups loved her.

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Cassidy F.
Sitter Profile Image: Mya R.
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Mya R.
from
$20
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
13 years of experience
Winchester, VA, 22601

Mya is a great help and takes the best photos!

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Robert B.
Sitter Profile Image: Myahrissa R.
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Myahrissa R.
from
$20
per visit
5.0 out of 5 stars
128 reviews
26 repeat clients
4 years of experience
Stephenson, VA, 22656

Mayahrissa is an excellent pet sitter. From our first meeting I could tell she really cares about animals and although I was a little nervous leaving my 3 month old puppy with a sitter for the first time, I immediately trusted Mayahrissa. During her visit, she followed all the care directions and sent me lots of pictures. My dog really likes her. She has a calm demeanor which puts pets at ease. I highly recommend her.

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Lorena C.
Sitter Profile Image: Charissa L.
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Charissa L.
from
$17
per visit
5.0 out of 5 stars
14 reviews
4 repeat clients
15 years of experience
Winchester, VA, 22601

Charissa gave me so much peace of mind while we were away! She cared for our pets while we were gone and sent meticulous, detailed updates each time she checked in with pictures and videos. I was a little nervous as Charissa was newer to Rover and didn’t have as many reviews as other sitters, but at our meet and greet I got a good feeling about her and I am so glad I chose her above others with more reviews. Highly recommend! Will use her services again for sure!

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Gina F.
Sitter Profile Image: Alex H.
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Alex H.
from
$18
per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22601

This was our first experience with Rover and it went very well. We were a little unsure of the process but it turned out pretty easy. We used Alex for drop in visits since we had to take our oldest back to school. He provided us with pictures and good feedback. It was important to us to have someone close and that had a love of animals. We would recommend Alex and will definitely be using his services again.

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Erin G.
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Over 265
pet parents in Winchester have booked cat sitting

Winchester cat parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Kim is the best caretaker for our pets when we travel. Great communication and pictures! She’s also very kind.

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Tracy A.
Drop-In Visits
5.0 out of 5 stars

Hannah takes such great care of my Opal. She is consistent and gives excellent updates. I can tell she actually cares about my pet when she is checking in on her/caring for her. 10/10 would recommend!

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Michelle L.
Drop-In Visits
5.0 out of 5 stars

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.

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Susan T.
Drop-In Visits
5.0 out of 5 stars

Timely communications, willing to gather the mail and water my front door plants. Kitty is also well taken care of. Thanks Alexsys!

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Mitsi L.
Drop-In Visits
5.0 out of 5 stars

Alyssa went above and beyond to give my cat love and attention. She followed instructions well and left the house in good shape.

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Kate S.
Drop-In Visits
5.0 out of 5 stars

Lisette did a great job of taking care of our cats while we were away. Fantastic at communication ( both responding to and asking questions). We would highly recommend her and plan on using her again the next time we are out of town

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Denis D.
Drop-In Visits
5.0 out of 5 stars

Miss Lauren has been amazing with my baby boys and brought ease to my mind while away on business. My furbabies were well taken care of and took to her very easily which brought me so much joy!!! She is my lifesaver and will furever be our go to caretaker!!!!!!

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Heather F.
Drop-In Visits
5.0 out of 5 stars

Amazing as always! Charissa provides exceptional care and gives detailed reports. Our fur friends adore her!

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Meaghan C.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by cat parents like you and choose a sitter who’s a great match for you and your cat
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your cat while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for cat sitting in Winchester is $20

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 cat sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total cat fanatics. You can get in touch with us anytime.

Sitters in Winchester average 6
repeat cat sitting clients

Cat Sitting FAQs

Frequently asked questions about Rover

Cat sitters on Rover are free to set their rates. The median cost to hire a cat sitter in Winchester on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A cat sitter’s rate may also change as you customize your booking to fit your and your cat’s needs.

If you’re searching for a Winchester cat sitter for the first time, visit the cat sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a cat sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 159 cat sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect cat sitter near you. As a reminder, cat sitters joining Rover must pass a background check for you and your cat’s safety.

Rover makes it easy to reach out to multiple cat sitters about your booking. Typically, 92% of Winchester cat sitters respond in under an hour.

Cat sitters in Winchester have an average of 16 years of experience. Cat sitters with repeat customers have an average of 6 repeat clients. Experience can vary from cat sitter to cat sitter, but you can view reviews, years of experience, and number of repeat clients when you compare cat sitters in Winchester.

Do you simply need someone to stop by and play, feed, and scoop? Winchester cat sitters are happy to take care of your cat while you’re at work, on vacation, or unavailable for the day, even if all you need is a quick drop-in! Your cat sitter will stop by to feed, play with, and snuggle your cat as many times a day as you like. And the best part? Your cat gets to stay on their home turf.

There are 159 cat sitters in Winchester on Rover, so you’re sure to find the perfect match for your cat! In Winchester, 95% of cat sitters offer daily exercise, 98% offer medication administration, and 93% have experience with senior cats and cats with special needs. We know each cat is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect cat sitter near you. As a reminder, cat sitters joining Rover must pass a background check for you and your cat’s safety.

Yes! Cat sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your cat sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your cat sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your cat is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your cat sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your cat sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your cat sitter’s cancellation policy.