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 147 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%.
About: I’ve assisted with dog sitting alongside my mom and grandma, helping with playtime, and companionship. I’m patient, attentive, and following routines to ensure dogs feel safe and cared for. Pet care fits easily into my daily routine. I have flexible availability as I am unemployed and already care for my own two cats and two bearded dragons daily. I provide attentive care in peoples homes, following routines closely. As an owner of two cats and two bearded dragons, I’m experienced with safety, cleanliness, and gentle handling.
About: What sets me apart is the trust I've built with my clients. Many are repeat clients who feel comfortable leaving their pets in my care, even for vacations lasting over a month long. I'm reliable, highly responsive, and believe communication is key. I'll keep you updated with photos and messages while following your pet's routine to help them feel safe, comfortable, and loved. From tiny cats to large dogs, I treat every animal as if they were my own and every home with the utmost respect, so you can enjoy your time away with complete peace of mind. I have a flexible schedule, which allows me to provide pets with plenty of attention, exercise, and companionship throughout the day rather than just quick check-ins. Whether it's walks, playtime, feeding, or simply keeping them company, I enjoy making sure each pet feels comfortable and cared for. As a pet owner myself, I understand the importance of consistency and sticking to your pet's normal routine. I always strive to make them feel safe, happy, and loved while you're away. I believe pets are happiest when they can stick to their normal routine. During overnight stays, I provide full care including feeding, fresh water, walks, potty breaks, playtime, cuddles, and any medications or special instructions if needed.
“Kimberly is kind and generous with her time! She made the Rover experience comfortable. I was excited that our fur baby would have someone genuinely interested in her wellbeing and clear on the expectations. I will definitely reach out again!”
“Heather was incredibly professional, kind, and patient with my dog CJ. He’s a large dog and can be cautious when meeting new people, and she did a great job reading his comfort level and building trust at his pace instead of forcing interaction. During our meet and greet, she was knowledgeable, realistic, and very aware of dog behavior, which immediately made me feel more comfortable. You can tell she genuinely cares about the animals she works with. Overall it was a lovely experience, and I would absolutely book with her again.”
About: Of all animals I have the most experience with dogs. I love dogs all shapes and sizes We've always had a dog at home and I have lots of experience, caring for playing with and walking dogs, including bath time. I'm a recent graduate of heritage high school. I took agriculture at school and worked with the animals on our school farm I'm looking to do rover as often as possible. I don't have any other obligations at this time. So I can dedicate myself to your pets. I am very careful about fences and doors. I'm mindful of owner instructions regarding where their pets can be. And where they are not allowed. I am mindful of them while they are eaten. And while they are playing, to make sure that they remain safe. I checked the pavement before I take a dog out on walks to make sure it's not too hot and always make sure to wash their bowls so that I can help prevent bacteria
“Krista was absolutely wonderful with my pups! She was so sweet and loving with them. She came to our house to get to know her and the pups before our event, which was very reassuring. Our dogs instantly loved her. She sent a lot of pictures to keep us updated and just made me feel so much better about leaving my dogs with someone. If you need a babysitter, she is the best.”
“Lucas was great with our 12-year old, feisty girl! He took great care of Janis while we were away for 10 days. He communicated well, and was a pleasure to work with. Lucas was the right fit and we could not ask for a better sitter/walker. Never missed a scheduled walk. When we came back our girl was happy and relaxed. Lucas will now be our go-to for when we need a sitter/walker.”
About: I’ve been helping my friends and family take care of their pets for years while taking care of my own elderly dog. I’ve helped with feeding, bathing, and medication for the animals and provide the upmost care for them. I’m currently available every day of the week at certain times due to college. Times im available are; Mon 10:30AM-10PM, Tues 5PM-10PM, Weds 10:30AM-1:30PM and 7PM-10PM, Thurs 3:30PM-10PM, Fri 6AM-10PM, Sat 6AM-10PM, Sun 6AM-10PM. I’d love to take care of any new furry friends and talk to you more about how it can fit into my schedule if you’d like to book! I’m very gentle with animals, if they’re afraid to approach me or be around me I’ll keep my distance to keep them calm as possible. I’ll set their food and water and wait for them to eat in their own time since I already have the habit of doing so with my own dog due to him being very picky about what he eats. I always keep a close eye on them.
“Breeanna is amazing! She takes excellent care of my cats and is very communicative. We are able to have worry free trips because we know we can trust Breeanna to take care of our fur babies. Thank you so much!”
About: I have experience working with puppies and many breeds. I will reinforce desirable behaviors through positive reinforcement. I have experience giving medication. I can take your pet to the vet for you. I have many years of experience working with animals at a veterinary hospital and animal shelter/rescue. I am available short or long term. I am available week days and weekends. Caring for pets is my vocation. I don’t have any schedule restrictions I have enclosures for the pet and a larger enclosed yard. I provide opportunity for water loving dogs to play in the pet pool. I provide “nose work” for those dogs that need mental activities.
“Ashleigh was so great with our 3 giant “puppies.” I loved having the daily reports and feedback. She caught the cutest photos of them too :) Highly recommend her services! Our doggos loved her. We will definitely request for her again.”
About: My love for animals I've had my whole life & cared for my own furr-babies my whole adulthood, Right now I care for my own 2 beautiful furr-babie cats myself & It wasn't until a couple of years ago through my house cleaning service & the relationships I built with my customers & there pets (which I still do) has provided me the experience to care for other pets. I have experience in house/dog sitting, a lil. Dog grooming, & visits to homes to walk, feed & play with, I've dog sat with puppies as well, I have the ability & knowledge to adapt to the animals personalities (because they are all different) but more Importantly I have so much love to give to all animals. I work part-time as a housekeeper during the week days. So my availability is pretty open after 3pm on the week days & my weekends are completely open for any time of the day & I can be available for house/dog sitting as long as I know a few days ahead time I can schedule my job around it no problem. Well Every pet is different with there own personalities & with that being said, It goes without saying first & foremost you have to respect the pet, the owner & there home as well as any care specific required. In other words we have to care for them just like there one of the family members by giving them all your love & attention needed.
“Our babies did so good with Estefany! She was prompt and thoughtful with her visits, sending us great photos letting us know the kitties were good to go. We’re very thankful! ❤️”
About: At age 16 I helped open up Homeland Pet hotel. I worked there 2 1/2 yrs. I was hooked. I have trained my dogs, my family and friends dogs and than helped with police K9s until I retired. I moved to Kentucky to work and be in an internship with a great training facility. In 2018 I moved back to California. I traveled and now I want to stay home and take care of or train your dogs. I take care and train all ages, size and breed of dogs. I have administered medications in all forms and I bath, brush and do nails. I am retired and I have the time and the means to help you and your pets have fun in life. I take my dogs to dog park and beach weekly when I am not camping. I am the person in my family everyone calls when they have a dog question. I am attentive, kind and playful, but I do have boundaries. I communicate very well with dogs and I'm pretty good with humans also. I have a 6 ft fence around my entire yard. I have my property sprayed for fleas and other critters every other month. It's a quarter acre property well maintained. I plenty of space inside for pets and I have several crates in all sizes if needed.
About: I have experience caring for both dogs and cats and have worked at a pet hotel, where I helped care for pets of different breeds, sizes, and personalities. I have a special love for English Bulldogs and French Bulldogs and understand the attention and care they need. Through my work and personal experience, I’ve become comfortable with feeding, walking, playtime, cleaning up after pets, monitoring behavior, and keeping pets on their normal routines. I’m available for overnight stays and understand how important it is for pets to feel safe and comfortable while their owners are away. As a self-employed house cleaner, I’m also experienced caring for clients’ homes and am known for being dependable, responsible, and trustworthy. I’ll treat your pets like family and provide updates and photos so you can have peace of mind while you’re away. Pet care fits naturally into my daily routine. I have a flexible schedule and make time for feeding, walks, playtime, litter box cleaning, and providing companionship. I enjoy spending time with animals and make sure they receive consistent care, attention, and love while their owners are away. Whether it’s drop-in visits, overnight stays, or maintaining a pet’s regular routine, I’m committed to keeping pets happy, comfortable, and well cared for. Safety and trust are my top priorities when caring for pets. In a client’s home, I follow all instructions carefully, including feeding schedules, exercise routines, medications, and any special needs. I make sure pets have fresh water, a clean environment, plenty of attention, and a safe space to feel comfortable. I also provide regular updates and photos so owners can feel confident that their pets are happy and well cared for. Having worked at a pet hotel and cared for pets throughout my life, I understand the importance of patience, responsibility, and treating every pet like family.
About: I have been a devoted pet caregiver and self owner since the age of 10. I have experience training and care giving for many different type of breeds such as huskies , poodles , jack Russell’s, German shepherds, pit bulls , and more. I always have experience with cats as well and love them just as much. My passion for the genuine care of animals is immense and I would strive to give the best service always. I have been fortunate enough to take some time away from my 9-5 and have had a dire need to pick up a hobby of something I genuinely would LOVE to do. My schedule is completely open to the needs of fur babies! I have one extremely friendly and loving husky who would love to engage with other pets just as much as I would. I have a large fenced backyard for play and gates that block off any potential hazards such as a open road.
About: Safe, loving care for your pup. Fenced patio, potty areas, and one friendly resident dog. Solo‑dog options available. Dogs must be child‑friendly for boarding. I provide walks, playtime, updates, and a calm environment for shy or social pups. Message me with your dog’s age, temperament, and needs.
The median cost per visit for pet sitting in Winchester is $25
Pet parents share their Rover experiences - Winchester
Sierra was absolutely amazing! We trusted her to care for our dog while we were away for a few days and she did not disappoint! She was kind, friendly and very easy to communicate with. She provided photos and updates each day which gave us the peace of mind that we needed. I would most definitely book with her again in the future!
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 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 $28.86 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 3,525 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:
- 90% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% 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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