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 36 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.
“Della took excellent care of our 5 cats over the Thanksgiving holiday so we could visit out of town family without worrying about them. Have always had very good service from her.”
About: I treat every pet like family, offering love, patience, and reliable care while keeping you updated so your pet feels safe, happy, and at home. Pet care fits naturally into my daily routine. I enjoy providing consistent attention, exercise, playtime, and affection while ensuring every pet feels safe and loved. I offer flexible pet care options, whether in my home or yours. I make sure each pet receives personalized attention, regular exercise, playtime, and plenty of affection, all while maintaining a safe and comfortable environment.
“Hannah did an amazing job taking care of my bunny boy! We did a meet and greet a few days prior to my leaving date, and she was very excited and happy to watch my bunny boy! Both of us got along great. Hannah is very good with communicating to me anything about my bunny boy. Loved the pictures she took and the comments she left! Will be booking with Hannah in the future!”
“Christina is amazing! This was our first time with Christina and we hit a home run. She went above and beyond to care for our babies, as well as, helping us out with things we didn’t even expect. She vacuumed up cat litter, collected our mail and took the trash out just so we wouldn’t have to do those things when we got home. And as wonderful as all that is, her care of our Tootie and JP was excellent! She spent lots of time on walks and play time and it was obvious our babies loved her visits and looked forward to them every day. I highly recommend Christina to take care of your pets. You’ll be glad you did.”
“Jenna is awesome and this my 2nd time booking with her. She takes wonderful care of my dog, is a great communicator, promt, and feel very comfortable leaving my dog in her care! I'm so lucky to have found her and absolutely recommend her.”
“Gabby did awesome, we've used her for years, glad to see shes stretching her arms and joining rover! Our dogs love her to death and she is great with them. All 3 are pitbulls and she has no issues Keeping them spoiled and happy! Would book her anytime ! A very responsible and respectful young woman .”
About: With 9 years of hands on experience caring for pets, I bring a flexible and intuitive approach to pet care that meets each pup where they are. Whether your dog needs a calm gentle companion, or a high-energy play, I adapt to their personality and needs. I have a little bit of experience with obedience training with puppies and can also care for senior dogs. I am currently only offering boarding, walks and drop-in visits but I am committed to making your dog feel safe, loved and right at home - even when you’re away! I am a recent graduate of UTC and just started working for Unum. I work from home most days but have to go into the office on Wednesdays and Thursdays! I’m available anytime that I’m not in the office as my at-home work hours are flexible. When caring for pets in your home, I first like to read the pets profile so I can see if there are any special instructions/needs that I need to know about. I offer a variety of services so how I care for your pet is based on what I am booked for. For walks, I like to find a safe/familiar place to walk them, like your neighborhood. I’ll usually walk them for the full amount of time and make sure they have water when we are finished. When dog sitting, I try to make sure I follow all instructions left by you, the owner. I usually make sure your pet has food, water, walks, and lots of cuddles/play time!
“Melanie was wonderful with our pets and went above and beyond to make sure all pets were happy and cared for. She was very patient to allow my not as friendly dog to come to her on her own terms and Lilly even let her love on her. Would highly recommend.”
About: I am friends and families go to dog sitter for when there is vacations, or someone is busy. I have been doing this for family and friends for a couple of years now im currently college student and would love to watch over your fur babies! with me being in school and work i’m normally pretty flexible with my schedule as all my classes are early in the morning! I have a huge fence around my yard and two adorable fur babies if yours are needing some company. I will be able to watch over your dog at all times if needed.
About: I have many years of caring for pets and ran my own kennel in Florida for about 13 years and was a Vet technician for 8years I’m available weekends and can also be on call if needed. I can also be available on some Wednesday’s and holidays I’m open to any times I will care for your pet as if they are my own fur baby and will provide what is needed to take the best care of your pet
About: Experienced dog-sitter looking to serve clients in the North Alabama area! My father has a senior boxer mix whom I care for on my parents' vacations and my aunt has a West Highland Scottish White Terrier that I drop in daily to take care of on their vacations, all with walks, potty breaks, feeding and watering, and accident cleanup! Message me to book a service today 😊 I'm currently self employed and will soon be working on a training program for Spanish to English medical interpreting so generally, I can make time in any schedule to care for your pet! I treat your home as though it were my own and your pet as though he or she were my own. I've been taking care of my aunt's Westie for 2 years without incident and so I'm your guy if you want an attentive carer that isn't going to just be "in and out."
About: I’ve spent my whole life around dogs and cats. I love taking them for walks, the park or helping them learn to swim. I know the importance of giving dogs medications and taking them to appointments. I also keep dogs well groomed while I watch them I currently work full time 5 days a week but but will spend all my free time taking care of your pets. I will check on them throughout the day during work if needed I live in an apartment that has 1 bedroom. The apartment complex does allow animals. I have ring cameras in my place and outside my place to make sure I’m always able to see if my home and the animals are safe
About: My name is Luke, I am a CATCH Canine Trainer Academy certified dog trainer. I use positive reinforcement to encourage and maintain behaviors. I have always had a passion for working with dogs but after losing one of my rescues to cancer only 2 months after saving her my passion grew. This had inspired me to help owners and their dogs learn and grow together. I am a Co owner of a food truck which we are only operating part time. On the opposite days I have open availability to help support you and your current fur baby. I am unable to offer boarding for animals at this time. I am certified in pet cpr and first aid through ProPetHero by Pro Trainings
About: I’ve grown up with dogs, cats, horses, you name it. Animals are underrated as members of the family in my opinion and I just want to make sure any animal in my care is treated like family. I take care of my animals (two dogs and a kitty cat) daily and they have a pretty set routine, I would be working my schedule around their routine and working on my days off. I’m happy to drop in and check on your babies and give them love and attention on long work days. I know how stressful it is to be at work knowing your baby is alone at home and I’m happy to help!
The median cost per visit for pet sitting in Winchester is $20
Pet parents share their Rover experiences - Winchester
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 pets like family
1. Search
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Popular requests for pet sitting - Winchester
Select a filter and find qualifying sitters offering pet sitting.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 $27.75 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 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 August 2026, there are 95 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a 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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