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 91 pet parents in Winchester have booked pet sitting
Winchester, Find top rated pet sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Can I give ten stars?? I am so happy we had James to look after our kitty while we were on a rare family vacation! The daily updates and the many pictures and videos were wonderful and made us know right from the start that we had the right person. I 100% recommend James for any pet-sitting job. Ray is happy we're back, but I can see he misses James now!! Thank you, James - you are awesome!”
“We have hired Cheryl many times and our pups absolutely love her!! She is so kind and attentive, her communication is wonderful as well! Thank you again for your continued care of our boys!”
“Wow. I could not be more happier leaving my fur babies in Lauren’s hands. She did an excellent job giving my one cat his medications and making both of them feel loved. She is a superstar.”
“Really great at communicating and very flexible! She took amazing care of my kitty and sent me a lot of photos while she was there. Would definitely book her again!”
“Sanela was such a wonderful caretaker of not only my beloved cats but also my garden during an insane heatwave while she was cat seating. She was communicative, shared a lot of information about how my cats were doing and she played with them so much I know they were happy and taken care of during my time away.”
“Sophia was amazing throughout the whole time! she went above and beyond and made sure she spent time playing with all three cats every day! she scooped the litter without being asked & we will definitely be hiring her again!”
“Sophia is EXCELLENT in all respects. She is very conscientious and amazing with dogs. She went above and beyond for us, addressing challenging issues in real time and responding flexibly when situations and needs changed. We are so grateful to have her caring for our dog!”
“I really cant say enough about how amazing Shawn was! She was so helpful as we were leaving our dog home alone overnight for the first time and also using Rover for the first time. She was super communicative, had so many great suggestions for how to arrange visits, and answered all our questions in detail. She is very professional and you can tell she cares a lot about the dogs she watches. Would book with her again in a heartbeat!”
“Angela was communicative and very patient with Kiba. In the short time that we had Angela watch him, he began to open up and show more of his personality. We would definitely have her come take of him again :)”
“Noila took amazing care of my two kitties for two full weeks! She sent daily pictures and videos of them playing, and included any other information about her check ins with them. She made leaving town so much less stressful! Fantastic experience.”
“Kerri is extremely flexible and wonderful with our pup. She is patient and kind. Our pup is the happiest to see her! She is definitely our go-to person to entrust our pup’s care !”
About: I know first hand how much love there is between a dog and their owner. For that reason, I believe trust, transparency, and fun are the pillars of my dog walking service. When you entrust me to care for your pet, I will make sure they are always safe, hydrated, and having fun! I also always send updates after walks letting clients know how the walk went and that dogs are home safe. As a dog owner, I have had family dogs ranging from a 6 lbs Yorkie to a 65 lbs Lab. Outside of my own pets, I have experience cat- and dog-sitting for friends and family and am excited to be able to take on more dog walking clients. I am comfortable walking dogs of many breeds, sizes and ages. I can't wait to meet your furriest family members! I am a graduate student, so I often have a flexible schedule to work around your needs. I am available for early morning and evening walks every day of the week and midday walks every day Wednesday-Sunday. Safety is my top priority for your pet, your home, and myself. This is why before working with your pet, I will request a meet-up with you to better understand your pet. In this meeting we can discuss if your pet has any aggression or fear around other dogs, escape-artist tendencies, or special needs so that walks can be as safe and secure as possible.
About: I grew up with dogs and cats and have cared for animals my whole life. In Ukraine I volunteered at an animal rescue and fostered pets, including birds, and once even looked after a bat through his winter hibernation. My own cat now lives with my parents, and I miss having a pet in the house — spending time with your animals would be a real pleasure for me. I worked in healthcare, so I'm comfortable giving oral and injectable medications and caring for senior or post-surgical pets. I'm calm and patient with nervous animals, reliable about schedules, and I'll send you photos and updates so you know your pet is doing well. I have a car and can travel to nearby towns. Happy to meet beforehand so you and your pet can get to know me. I'm currently studying for my medical board exams from home, so my schedule is very flexible and I'm available throughout the day, including mornings, midday visits, evenings, and weekends. I don't have pets or children of my own, so I can give your pet my full attention. I have a car and can travel to nearby towns. Advance bookings are easiest for me, but I can often accommodate last-minute requests. I care for pets in their own home, where they're most comfortable and can keep their normal routine. At our meet-and-greet I'll go over your instructions in detail: feeding amounts and times, medications, walking route, favorite toys, house rules, and what to do in an emergency, including your vet's contact information. I follow your instructions exactly rather than my own preferences. Dogs stay leashed outdoors unless you tell me otherwise, and I check doors, gates, and windows before leaving. Beyond food and clean water, I make sure each pet gets real attention — play, walks, brushing, or just quiet company, depending on what your pet enjoys. I send photos and updates after every visit, and I'll let you know right away if anything seems off, like changes in appetite, energy, or bathroom habits. I'm also happy to bring in mail, take out trash, or water plants while you're away.
About: I've loved animals for as long as I can remember. Growing up, my family always had pets, including dogs, cats, and rabbits. Caring for them taught me responsibility, patience, and how to understand each pet's unique personality. I know that leaving your pet with someone else can be stressful, so my goal is to make both you and your pet feel comfortable and confident. I treat every pet as if they were part of my own family, providing plenty of love, attention, playtime, and care based on their individual needs and routine. Whether your pet enjoys long walks, interactive play, quiet companionship, or simply sticking to their daily schedule, I'll make sure they feel safe, happy, and well cared for while you're away. Communication is very important to me. I'll send regular photo and video updates, along with messages about how your pet is doing, so you can enjoy your time away with peace of mind. I'm available for last-minute bookings whenever possible. I have experience caring for puppies, senior pets, and multi-pet households. I'm happy to follow your pet's feeding schedule, medication routine, and any special instructions. I am currently working part time and have sufficient extra time to care for your kitten or cats! My availability is before 11 am and after 1pm daily. I have an apartment with a yard to walk around within gated community if needed. Additionally, it is on the ground floor for convenience or easy access.
The median cost per visit for pet sitting in Winchester is $25
Pet parents share their Rover experiences - Winchester
Caitlin was wonderful with Latte! She was incredibly caring and patient, and I loved seeing Latte slowly grow to trust her even though she was initially very nervous. Caitlin's daily notes and photos gave me so much peace of mind while I was away. She also went above and beyond by taking great care of my fish and plants. I’m so grateful for everything she did and would absolutely trust her with Latte again!
Katina has been a delight and everything I needed. I had knee surgery and needed help feeding my cat, Max, plus he needs insulin injections twice a day. All of that went well because he absolutely loved her. Anyone could feel comfortable knowing their pet is in very capable hands. I feel like we have a new family friend. Karen O'Sullivan
Carmen has been wonderful with our two dogs! The big one just loves cuddles with her and the small one loves playing fetch with her. We have engaged Carmen for regular drop ins and also special dates when we had to be away. She has always been super reliable and a very clear communicator.
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 to book pet sitting
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
It's that easy! All payments are processed through Rover's secured platform.
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 of Pet Sitting in Winchester on Rover is $32 per visit as of October 2026. Most bookings cost between $16 and $44 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 10,692 sitters on Rover offering Pet Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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:
- 89% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 94% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
sitters on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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