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 458 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 !!!”
“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!”
“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!”
“Christa did an absolutely fantastic job. She was available on short notice, friendly, professional, responsive, and did very well with handling my rambunctious pup. I highly recommend her services and will be requesting them again myself in the future.”
“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!”
“Alexsys took wonderful care of our two cats while we were on vacation. She went above and beyond, and we’ll definitely book her again! We can’t recommend her highly enough!”
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.
“We had a wonderful experience with Courtney! I accidentally booked the wrong weekend for our cat care, and as soon as I realized the mistake and contacted her, she immediately offered to head right over to take care of my kitty. That level of kindness, flexibility, and reliability meant so much to me, especially while traveling over a holiday weekend. She stayed for at least a full hour each visit, sent tons of photos and detailed updates every day, and clearly spent quality time making sure my cat was comfortable and cared for. The updates really helped me relax and enjoy my trip knowing my kitty was in such good hands. I truly appreciated her responsiveness, professionalism, and genuine care for animals. I would absolutely book with her again and highly recommend her to anyone looking for a dependable and thoughtful sitter!”
About: Everyone calls me when they need a reliable and dedicated pair of hands to watch over their children. Yes, I treat every dog like a furry child. I've helped raise dogs from 6 weeks to 16 years old. The young and the old need a little more attention and I'm happy to help. Those terrible 2's just need extra attention, and I'm happy to provide that too! I love all animals and will probably treat the kids like royalty. I prefer the company of dogs than my friends, they could vouch for that! I'm both loving and also stern because I've raised both labs and pitties. They require different types of parenting techniques, and I am equipped to handle anything. I work full time, Monday through Friday, 9 to 5. I'm happy to use my work breaks to check on animals for those who need the extra attention. My availability will be based around my work and my 2 kiddos at home. I can adjust weekly routines to incorporate pickup/drop offs, stop in visits, after work walks, or overnight stays. I treat dogs like they are our kids. I talk to them, I cuddle with them, and I use positive reinforcement to train good habits. I've helped raise a dozen dogs and each dog likes to show you how they like to be treated. I learned this lesson the hard way when I was raising dogs and had to learn different techniques to train each of them individually. Labs learn and function much different than bulldogs and pitbulls. I treat each dog the same regardless of size or attitude. Though I may give them some attitude when mouth off, like I do with my pitty at home (lol). I'm a safety first kind of person when it comes to our kids. So I tend to lean on the side of caution and extra equipment when interacting with most dogs. I always keep extra dogs supplies in my truck at all times as I have been known to that guy who stops traffic to try to rescue a dog. I've done this probably 6 or 7 times.
“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.”
“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 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.
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
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: Hey there my name is Allison and I am a huge animal lover! I will love on your fur babies while you are gone and make sure they have what they need! As someone that has every pet but a dog of her own and has always wanted one, I will completely take advantage of the time I get with yours! I am comfortable with whatever is in need feeding, walks, backyard play, even just hanging out at the house and keeping your animal company! I have experience with a wide range of animals and I will make sure your needs are met! I am so excited and looking forward to meeting you and your sweet fur baby! Whatever animal comes my way I will make sure they are taken care of!
“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.”
The median cost per visit for pet sitting in Winchester is $20
Pet 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.
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet & Greet
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 near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 5 repeat pet sitting clients
FAQs for Drop-In Visits - Winchester
Frequently asked questions about Rover
The average cost for Pet Sitting in Winchester on Rover is $22.2 per visit (as of July 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 July 2026, there are 918 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:
- 91% of sitters can help with special care needs
- 99% can help with giving oral medications or injections
- 95% 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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