Pet Sitting Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 465 pet parents in Winchester have booked pet sitting
Winchester, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I had a wonderful experience with Kim this past week!!! She kept me updated more than I even expected and my dogs were beaming in the photos she shared with me !! I will certainly be enlisting her help in the future !!!”
About: I’m new to the area and looking to help out with the furry friends in my neighborhood! I’ve grown up around dogs and cats since I was young, and love getting to spend time with them, whether it be taking them on walks/runs, playing with them, or just giving them lots of love and attention. I am reliable, with my own transportation and a flexible schedule! I am a new graduate student at Shenandoah University - as a musician I have a few rehearsals in the afternoons and evenings, but my schedule is pretty open otherwise and I’ll have plenty of time to stop by/stay over and keep your pets company! I am a rule follower! I will follow your guidelines to a T, and make sure your pet is cared for exactly as you wish. I know that pets are our whole world, and leaving them with a stranger can be nerve wracking - I am reliable and responsible, and you can easily trust me to take care of your loved ones!
About: I’ve taken care of dogs and cats of all sorts. I grew up with small, medium, and large dogs as well as indoor and outdoor cats. I’ve also grown up caring for animals from a variety of backgrounds- fosters, rescues, you name it. I genuinely love spending time with animals and since I can’t have one of my own this seems like a great way to connect with pets and offer my services. I’m happy to come meet any animals in advance to make you more comfortable. I currently work remotely 90% of the time so this gives me a lot of flexibility to walk and take care of animals during work day hours if needed. I’m very good with following whatever directions will make you and your pets feel the most comfortable in your homes and out on walks.
“Juliana was great! Sent me updates and pictures multiple times a day. Bunny was very comfortable with her and when I came home she was so relaxed. I would definitely recommend her!”
“Charissa is amazing! Our plans changed more than once and she stayed flexible working with us. We received beautiful pictures of all our dogs and updates for every visit. Her rates were very fair and she even cleaned up without being asked! We will be recommending her services to family and friends while also asking her back to our home. We love her and our pups do too!”
About: I have been a pet owner for most of my life. I volunteered at the SPCA while I was in college, and I thoroughly enjoy interacting with animals. I will care for yours as I cared for my own! While my daughters are in school, my day is open! I can visit, walk, and play with your pet while you’re at work, so you won’t have to worry if they’re bored or lonely. I will come to your house to walk, feed, and/or play with your pet. We can discuss your pet’s needs at any time.
“We were very pleased with Hannah! She was so prompt with her visits, sent detailed and informative communications regarding activity, sleeping, medicine, their walks, and took plenty of pics of our girlies. Everything worked like clockwork and went just fine. Thank you Hannah for loving on our girlies while we were gone!”
“We rehired Alex to look after our big dog Rocky again for a week while we celebrated our anniversary. He did an amazing job and kept us updated with pictures of Rocky and rocky looked like he was having a blast in all the pictures. Alex played fetch with him in our yard daily and made sure Rocky had enough toys to play with. We came home to a happy dog and we are very grateful we could celebrate our anniversary without worrying about how Rocky was faring back home thanks to Alex!”
About: I’ve loved animals my whole life, and I’ve had the pleasure of living with, and pet sitting for multiple cats and dogs. I’ve done both kitty and dog meds, so if you have a high maintenance fur child like me, I’ve got you covered!! If you trust me with your fur baby, I promise I will love them as much as I love my own!! I work from home, so I have a lot of flexibility. Mornings are more difficult for me, but I can definitely work with you to find what’s best for the pets! My own pets are high maintenance, so I am definitely able to work with your pets needs. I crate my own dog, and give both my dog and cat meds and supplements. I don’t have any human children so my pets are my children. I will give your pet the love, attention, and care I give my own!!
“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!”
“Courtney was absolutely amazing with my new puppy and older dog! She is very responsive and attentive to their needs! Do not hesitate to book her services. Your pet will be in great hands!!”
About: Hi there, my name is Kristina and I’ve just recently moved to the Winchester area! Caring for animals has always been one of the greatest joys in my life. With years of experience, looking after pets of all ages, personalities and needs I’ve built a reputation for being reliable, attentive and genuinely invested in each animals wellbeing. One of the biggest advantages of working with me is that I work from home full-time, this means that your pets will never be left unattended and I am able to give them consistent attention to ensure they feel safe and comfortable throughout the day. When your pet is with me, they’re treated like family whether it’s daily walks, playtime medication reminders or just offering affection and companionship, I make sure every animal feels loved and understood. I look forward to giving your pets the dependable, worry free care they deserve. I currently work from home Monday through Friday. I have the ability to visit your home and ensure your pets are doing well and to provide them any enrichment they may need whether it be walks or play. I currently live in townhouse with my husband and our dog, named Gorgi (Gorgonzola), we go on frequent walks in the morning afternoon and evening. We keep a clean home and have a basement that lets out into a small backyard. I have one X-Large kennel if your pup prefers to sleep in one as well as a puppy pad corner for those late night bathroom breaks. I would be happy to provide a tour our home upon request.
“Great job! This was the first time we were away for an extended time since getting our kittens and our first time using Rover. We're glad we found Christa. She did a wonderful job and kept us updated with pictures each visit. She was also quick to respond to any questions we had. 10/10 would recommend!”
“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.”
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.
“Myahrissa took exceptional care of my dogs, Naya and Francis, and I could not have been happier with the experience. From the moment she met them, it was clear that she genuinely loves animals and treats them as if they were her own. Throughout her time with them, she was attentive, caring, reliable, and communicative, giving me complete peace of mind while I was away. Naya and Francis absolutely adored her, and it was obvious they had an amazing time together. When I returned home, they were happy, relaxed, and well cared for—one of the best indicators that they were in great hands. I would highly recommend Myahrissa to anyone looking for a trustworthy, compassionate, and professional pet sitter. She went above and beyond, and I would not hesitate to have her care for my dogs again in the future.”
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!
The median cost per visit for pet sitting in Winchester is $20
Pet parents share their Rover experiences - Winchester
Kim is kind and caring and really takes the time to make sure my furbabies are loved and everyone is doing well. She doesn’t hesitate to bring in packages, tidy up messes left by the babies while I’m away, and even clean up messes in my front yard. I expressed to her some concerns I had given a recent health issue for one of my cats right before my trip, and even though that cat was too shy to let Kim check on him she still took the time to check for any other signs of health issues around the house. I feel so comfortable knowing she is checking on my babies while I’m away!
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!
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 pets like family
1. Search
Browse profiles of sitters near you who offer pet 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 pet sitting - Winchester
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winchester average 6 repeat pet sitting clients
FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
The average cost for Pet Sitting in Winchester on Rover is $22.2 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .
As of September 2026, there are 864 sitters on Rover offering Pet Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winchester stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
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.
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.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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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