Pet Sitting Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
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.
“It was so nice having Kat care for Binx! She was extremely reliable and very communicative- sending loads of pics and lots of “news” from home. I absolutely would use Kat again and am relived to have found someone I like who is trustworthy and took care of everything I asked her to.”
“Megan did another fantastic job of taking care of our cats and handling our constantly changing medicine needs. She sent great pictures and updates and clearly cares very deeply for the animals she takes care of! We hope to have her back to watch our cats again!”
“Pamela was a great sitter for our sweet kitty, Penny! She sent thoughtful updates each day and always made sure Penny got what she needed (snuggles, play, or some tv time!). She also handled Penny’s complex feeding and made sure she had all her meds completely correct. We’ll be sure to have Pamela back to watch Penny.”
“Shawna was amazing. She stepped in last min, got me out of crisis mode, worked with my two kitties beautifully, was communicative, responsible, kind, I will rehire her in a heartbeat.”
“Rashell (pronounced Rachel) did a fabulous job! This was my first trip without my 5 yr. old English bulldog "Muriel", and there was considerable separation anxiety. Rashell handled it like a pro, and she and Muriel are now lifelong friends. I'll be using Rashell again during my next trip in April '24, and I encourage all of you to use Rashell as well - you won't be disappointed!”
About: I have hands on experience caring for dogs of all sizes and temperaments, including my own pup, Silas. I’m familiar with feeding schedules, administering medication, potty routines, walks, and active play. I create a safe, loving environment where dogs feel comfortable and happy. I also have experience caring for multiple pets at once, so I’m skilled at managing different personalities and energy levels. Pet care fits easily into my routine, and I’m happy to make time for your pets and their needs. I have a flexible schedule and can provide regular walks, playtime, feeding, potty breaks, and plenty of love and attention. I’m reliable and enjoy making sure pets feel comfortable, safe, and cared for while their owners are away. I treat every pet and home with the same care and respect I would want for my own. I make sure pets are safe, comfortable, and supervised while following their normal routines, including feeding, walks, medications if needed, and playtime. I’m respectful of clients’ homes, keep things clean and secure, and communicate with owners throughout the stay so they can have peace of mind while they’re away.
“Jewels was a great pet sitter for our Betsy Lu! She was excellent in communication and remedied issues that came up during our time away. We will look forward to hiring her again in the future!”
About: I have been an animal lover since I was born! I grew up on a farm that included all farm animals; mainly horses, dogs, and cats. I’ve had many years of experience with training, and proper pet care! I currently work from home and I have plenty of time throughout the day for pet sitting! I’m available 24/7 I enjoy walks, and nature so I spend a lot of time outside. I have a large fenced yard, fit for animals. We have a loving friendly 7 year old hound dog named Copper. We live in a safe quiet neighborhood close to trails and parks.
About: I have been around dogs and cats for a couple years now. I have a dog and have had her for a year now. I understand the importance of going on walks and dedicate some play time! I am very patient and loving when it comes to animals. I’m currently working part time so I have some time to spare. Due to this, my work schedule isn’t always the same each month. But I would love to make some time to help take care of some cute doggies and cats! I have taken care of different kinds of dogs. I rescued a dog from the shelter so I have experience with taking care of animals that can be a bit more difficult. I am willing to clean up messes. I am very patient with animals and I will give them lots of love:)
About: I can care for a wide variety of animals. Care will include lots of physical and mental stimulation, as well as anything else you’d like! Let me know if your animal(s) needs any additional care such as medication administration or needs to be kept separate from other animals, and I will be more than happy to accommodate your animal’s needs. There will also be an opportunity to become a private client to avoid the insane Rover fees, so you can save money and I get the full amount that you pay! (Currently, Rover takes 20% of my pay AND charges you even extra!) I do have full time school 3 days a week, so will be gone a good part of the day during those days. Dogs are required to be crated while I’m away. I will do my best to be flexible and use effective communication with all my clients. I have 2 dogs, a cattle dog and a golden retriever. I also have 2 cats at home as well. Let me know in advance if your animal(s) are reactive or aggressive to people or dogs. All dogs will have plenty of physical and mental exercise, and anything else that they need during the day. Bring toys, food, leashes, crates, and whatever else is needed at drop off.
About: I have not only taken care of my own pets but have fostered and rehomed numerous cats and dogs for over the last 10 years. When I lived in North Dakota, I volunteered at the local humane society and adopted an old German Short-haired pointer named Billy in the process. I have experience in handling large dogs such as American Bulldogs to small dogs like little chihuahuas, along with cats, reptiles, and birds. I am always eager to hear about individual personalities and ways you have learned to better care for your companion! I currently work part time but am available for pop ins, evenings, and over nights. I can also do morning and evening walks. I look forward to doing more of what I love! I have taken care of animals with special needs such as the hearing and vision impaired. I have helped administrator multiple medications and used to animals with a wide variety of personalities. I am very knowledgeable in verbal and nonverbal cues and can spot and diffuse the situation quickly. My experiences over the last decade are why I'm confident that I can provide top notch care for your loved ones when you're away!
About: I am passionate about our animal friends and hope to add more pets to my daily life! I especially love pup time and am always excited to meet more friends. I’d love to help you and your family by offering quality, caring service to your pets. (: Currently I am offering sitting and drop-in visits seperately but due to health needs I am most able to provide exercise, energy expenditure and mental and physical enrichment either from your home or via outings. I do have a service dog that accompanies me most places and he loves making new friends, which can be a great option if yours also enjoy regular playdates. He is good with kids, cats and other dogs, if you have any questions feel free to ask! I am always open to making other arrangements based on your needs and prioritize finding accessible solutions and making accommodations to ensure your pets are able to recieve quality care. (: I am available in the morning through evening as well as overnight! I’d love to work around your schedule and to help make things as accessible as possible! Currently I am not offering boarding or daycare in my home. I am in a shared living space and unfortunately don’t have enough room for more furry friends at this time.
About: I absolutely love dogs ! They truly are man’s best friend till the end. I have two dogs of my own , whom I love very much ! I have experience in dog sitting as well as dog walking and I am passionate about providing good care and excited to meet new pups! I fit pet care into my day/week routine because I have two dogs of my own. One is a pit bull and another is a boarder collie so to say they need care is an understatement. They have the upmost energy. I will play with them and wear them out so they get a good nights sleep. With that being said we walk, hike, run, go to the beach, play fetch , etc. as much as we can. I treat my puppies very kindly , if not they’re quite spoiled. 😉 I care very deeply about animals and I aim to help when I can !
The median cost per visit for pet sitting in Winchester is $20
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
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Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for pet sitting - Winchester
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winchester average 4 repeat pet sitting clients
FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
As of September 2026, there are 50 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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