Pet Sitting in Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winchester pet sitters

“Maura accepted our last-minute request to provide drop-in care for our cats and bird when an unexpected trip came up. We trusted her from our first meeting with her and she did a great job! She communicated with us and sent photos from every visit. We will definitely reach out to her when we need to travel again!”


“Saraya is great! She is very responsive and sends pictures and a message after each visit! We have loved having her watch out cats and appreciate the extra things she does such as cleaning the dirty cat dishes!”


“Ella did a great job taking care of our two golden retrievers in our home. She did everything we requested and communicated well.”


About: Cared for rescue dogs for 18+ years. Different needs and personalities! Love it! I will give your pet the same unconditional care and love I give my own. I’m retired from my job and have a flexible schedule to care for your pet. Reach out any time. I appreciate the opportunity to care for your pet. I am willing to care for your pet in your home, drop ins or take them for a walk. I can give medicine and feed them. In addition to lots of love and care.

About: I've had pet dogs (and cats) my whole life! I've always loved animals and started caring for my pets at a young age. I also pet sit for my family on occasion. I promise to care for your fur babies as if they're my own 😊 I have an open schedule currently! I can care for your pet(s) whenever is convenient for you. Whether it's overnight stays or a quick drop in, I've got you covered! I will stick to your pets feeding and potty break schedule. If there are any special requests, just let me know. And I'll be sure to give them lots of love!

“We really like Caidan, he is wonderful and we feel he is the perfect person to stay with our girl Luna. We are so extremely thankful and feel comfortable leaving our baby in his hands. Thank you so much Caidan!”


About: We love dogs! We have a female English massiff that stays inside, and currently care for 4 hunting hounds in our outside kennel. I can care for your dog any way that you see fit. If you are more comfortable with your dog staying in their own home I can do that. I am also available for drop ins. And walks. I do work a part time job Wednesday- Saturday 9:30-5pm. I have 3 children so your pet must be friendly with children. We are a dog loving family. We look forward to hearing from you and getting to know you and your wonderful dog. Feel free to ask me any questions. I currently work a part time job from 9:30am-5pm Wednesday- Saturday. On my days off and before and after work I will have time to spend with your dogs. I currently am not offering sitting at my house. But I’m more than happy to care for your animals at your home, providing any services that you need.

“Veronica was so great with my cats. They were well taken care of and it was a big relief to know they were in good hands. She was dependable and I appreciated her communication in sending updates and photos from each visit. She not only took affectionate care of my pets, but she also looked after my apartment as well. I recommend!”


About: I have pet sit for many years. I love meeting new animals. I enjoy pet sitting because as a social worker I am able to come home to an animal and sent time with them. Animals are the way I cope. I have plenty of time to play with animals in the evenings and weekends. My schedule is very open for this and I am excited to have this opportunity I will ensure to keep everything the way I found it or even better. I know animals do best in their own environment so I have no problem being in other peoples homes. I show respect.

About: I have experience taking care of animals, it’s my favorite thing to do. I would love to continue to learn and meet other animals to care for My schedule is pretty open at the moment, would love to avoid weekends if possible but I am willing to work anytime, until my schedule is more full I love spending time with the animal I am in charge of, whether it’s walking or playing outside or inside and just sitting on the couch. Whatever the animal would need

About: We’ve had dogs of all sizes in our home since I can remember. And I’ve raised a few of my own along with 2 cats I am available all week. I can check in on your pets and let them out and feed them according to your routine. I will also walk your pets. I can also board and host daily care of multiple pets. You can leave me any detailed instructions on how you’d like your pet cared for. I’ll come in and take them out into the yard to do their business, or change their pads/clean up cat litter and clean any messes they may have left. If they need to be fed I’ll give them food and water also according to your instructions. And if they need to be walked around the neighborhood or park I can do that also. When they are in my home you can bring toys, beds, or Blankets that they feel more comfortable in, but I can provide that as well. You may bring your own food that does well for their diet.

“Absolutely amazing sitter for our loves. Went above & beyond! 100% will be my go-to sitter when needed! Nothing but positivity with Jackie!”


About: I have been around dogs and livestock my entire life. I currently work at a veterinary clinic as a receptionist and am going to school to become a veterinarian hopefully. I look forward to see you and your fur babies. I’m currently a student at Ball State. I have a lot of downtime after 5pm or so. I also have breaks in between classes. Let me know what you need and I will make it work! I have 3 dogs currently, that are all very social and loving. But can be put up if your fur baby gets nervous or anything else.

“Jeremy did so well with my difficult dog. Tobin was a quarantine puppy and didn’t get a lot of socialization but Jeremy was very understanding and did phenomenal. We are so thankful for all the help he provided us with, with such little notice.”


About: I will train the puppies how to give commands. Training will be conducted according to the pet habits of different customers. Dog walking, feeding and bathing services are also available. I can provide you with the status of your pet in real time, so that you can clearly understand the daily actions of your pet and record it. I will take classes every Monday and Wednesday, and I can do part-time work the rest of the time. I can take care of pets from 2pm to 8pm. If you have any other needs, please contact me in advance and I will arrange the time. We connect the cage to the backyard so that the pets can come and go freely. I accept each client's feeding style and I hope we can communicate before the appointment so that I can make a reasonable feeding based on your situation. I will take care of pets in your home, I will protect your personal property, and I will carry a video camera with me for recording.

About: I have had pets since I was little, and am very knowledgeable in dog behavior. I have been in daycare settings for children, so I will treat your pups care like I do with daycare kiddos, I will be very communicative to you, and send you pictures. I have trained multiple puppies in my lifetime, and have had a couple of senior dogs. I have had Labs, one Doberman, and Pugs. I have also raised two litters of puppies. Currently, I have an English Bulldog/Sharpei mix who is 11 months and constantly learning new things about behavior, and how to manage it. I am always learning new things about dog behavior and training as it is one of my passions. I will treat your fur baby as my own. I am excited to get to know you and your fur baby. Pet care fits into my daily or weekly routine because I am at home and I am excited to start taking care of other peoples pets. On the weekends at the moment I can fit in some later shifts, it is not listed, however I can. I will care for your pets the way you want me to take care of them. Tell me what you want me to do, and I will do it. These are your babies. I want to learn everything about them and care for them the way you care for them.

About: Most familiar with cat care all the way from little kittens to senior cats. I do dog walks and dropin visits on the Wag app and have a perfect 5 star rating for every job I have done and am looking to expand my clientele here. I absolutely love being able to care for pets and see how happy they are when we go for walks or play fetch. I also dogsit my family's golden doodle who is learning tricks and has anxiety around people. I have a part time job and do contract work on my own schedule so I can fit pet care around my current schedule easily. I intend your home space to be the same as you left it when you return from your trip with a happy pet waiting for you.

About: I grew up with 3 large breed dogs and have done 2 years of dog walking / pet sitting! During my 2 years of pet sitting, I took care of puppies from 6 weeks old to senior dogs. Things that fell under the description of ‘took care of’ are; picking up poop, feeding / following dietary schedules, administering medications, walks, play time, bathroom breaks, training work, mental stimulation (snuffle mats, kongs, etc.) I do daily dog walks, and am helping my parents raise and train a German shepherd! I also have 2 cats of my own at home. I will travel to your home by car! I do not offer care for your pets in my home due to my cats not being very sociable haha!!

About: I love animals and I’ve been around them most of my life! I have a dog of my own that I’ve had for 8 years, so I’m very familiar with their behaviors and how to take care of them! Pet care fits into my daily routine as I am currently studying Wildlife Biology and minoring in Aquatic Science at Purdue University. I believe this will be the perfect opportunity to get me started in my animal career! I live in town so it’s perfect to take your dog on a walk whenever they need to go outside! I do have a crate if needed and I have a small dog of my own that I’m sure your dog would love the company. Also, I’m willing to take care of your pet at your home so whatever routines you have to take care of your pet I will follow! I love taking pictures of my pets, so I can definitely take some of your animals too.

About: I've worked in a boarding facility, cleaning up after dogs and cats, warming up to them if they're nervous, playing with them, and of course giving them lots of pets!❤️❤️ I'm free to take care of your pet full time! I'm also a doordash driver so I fit that into whatever time I'm not scheduled to play with your pets! I'm very adaptable. I can work in an apartment, or a home, I believe the best pet care starts with the setting. If your dog or cat is taken care of in your house they'll be much more comfortable, since they're used to the environment
Loving pet sitters in your neighborhood
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Maura Y.

“Maura accepted our last-minute request to provide drop-in care for our cats and bird when an unexpected trip came up. We trusted her from our first meeting with her and she did a great job! She communicated with us and sent photos from every visit. We will definitely reach out to her when we need to travel again!”


Saraya T.


“Saraya is great! She is very responsive and sends pictures and a message after each visit! We have loved having her watch out cats and appreciate the extra things she does such as cleaning the dirty cat dishes!”


Ella M.

“Ella did a great job taking care of our two golden retrievers in our home. She did everything we requested and communicated well.”


Angela D.
About: Cared for rescue dogs for 18+ years. Different needs and personalities! Love it! I will give your pet the same unconditional care and love I give my own. I’m retired from my job and have a flexible schedule to care for your pet. Reach out any time. I appreciate the opportunity to care for your pet. I am willing to care for your pet in your home, drop ins or take them for a walk. I can give medicine and feed them. In addition to lots of love and care.


Jessie P.
“Jessie is excellent with pets. I've entrusted her to care for my dog and visit my house to feed and care for my cats as well when I'm not able to. She always puts their needs and wants first and takes the necessary steps to ensure they get enough cuddle time and social interaction and goes above and beyond to put them first every time.”


Caidan R.

“We really like Caidan, he is wonderful and we feel he is the perfect person to stay with our girl Luna. We are so extremely thankful and feel comfortable leaving our baby in his hands. Thank you so much Caidan!”


Beth C.
“Very grateful for Beth's excellent care of my two dogs. I always get so nervous leaving my pets but I was very at ease with Beth. She sent videos of my puppers enjoying their treats while I was away. I will definitely use her again and would recommend her to anyone that need a great pet sitter!”


Veronica C.

“Veronica was so great with my cats. They were well taken care of and it was a big relief to know they were in good hands. She was dependable and I appreciated her communication in sending updates and photos from each visit. She not only took affectionate care of my pets, but she also looked after my apartment as well. I recommend!”


Mykhail M.
“She has done such a good job watching my dogs. I needed someone to watch my dog last minute because I needed to help my mom in another state. She rush right over that same night. She treats my dog like they are family. I highly recommend her.”


Skylar M.
About: I have experience taking care of animals, it’s my favorite thing to do. I would love to continue to learn and meet other animals to care for My schedule is pretty open at the moment, would love to avoid weekends if possible but I am willing to work anytime, until my schedule is more full I love spending time with the animal I am in charge of, whether it’s walking or playing outside or inside and just sitting on the couch. Whatever the animal would need


Aydee M.Star Sitter
About: We’ve had dogs of all sizes in our home since I can remember. And I’ve raised a few of my own along with 2 cats I am available all week. I can check in on your pets and let them out and feed them according to your routine. I will also walk your pets. I can also board and host daily care of multiple pets. You can leave me any detailed instructions on how you’d like your pet cared for. I’ll come in and take them out into the yard to do their business, or change their pads/clean up cat litter and clean any messes they may have left. If they need to be fed I’ll give them food and water also according to your instructions. And if they need to be walked around the neighborhood or park I can do that also. When they are in my home you can bring toys, beds, or Blankets that they feel more comfortable in, but I can provide that as well. You may bring your own food that does well for their diet.


Jackie K.

“Absolutely amazing sitter for our loves. Went above & beyond! 100% will be my go-to sitter when needed! Nothing but positivity with Jackie!”


Raven D.
About: I have been around dogs and livestock my entire life. I currently work at a veterinary clinic as a receptionist and am going to school to become a veterinarian hopefully. I look forward to see you and your fur babies. I’m currently a student at Ball State. I have a lot of downtime after 5pm or so. I also have breaks in between classes. Let me know what you need and I will make it work! I have 3 dogs currently, that are all very social and loving. But can be put up if your fur baby gets nervous or anything else.


Jeremy W.

“Jeremy did so well with my difficult dog. Tobin was a quarantine puppy and didn’t get a lot of socialization but Jeremy was very understanding and did phenomenal. We are so thankful for all the help he provided us with, with such little notice.”


Yiguo W.
“When I go on business trips, I also leave Jim with the dog walker to take care of him for a few days. Every time I get home, Jim still feels a little reluctant.”


Amanda C.
“I have known Amanda all her life and have watched her train and care for a variety of animals. I have Dobermans and she helped me post their ears. She was most persistent to get the ears to stand perfect, and they did! I trust her caring for my animals!”


Mary D.
“Four cats and a dog while growing up....at least three cats since she's been on her own. Throughout it all, she has been a responsible caregiver, trainer, exercise supervisor, dietary technician, and trusted companion. Your pet(s) will enjoy her every bit as much as her own do . . and did!”


Abby H.
“We have used Abby several times over the last two years to help care for our puppies. We have two boxers who now love Abby and when she comes to visit them. She ensures she is on time, and spends quality time with our dogs. They love to see her coming because they know she loves to play with them and take them for walks. Abby does a great job communicating and letting me know if there are any concerns and how the dogs are doing. It is a great peace of mind to have her when we are out of town.”


Aubrey J.
About: I love animals and I’ve been around them most of my life! I have a dog of my own that I’ve had for 8 years, so I’m very familiar with their behaviors and how to take care of them! Pet care fits into my daily routine as I am currently studying Wildlife Biology and minoring in Aquatic Science at Purdue University. I believe this will be the perfect opportunity to get me started in my animal career! I live in town so it’s perfect to take your dog on a walk whenever they need to go outside! I do have a crate if needed and I have a small dog of my own that I’m sure your dog would love the company. Also, I’m willing to take care of your pet at your home so whatever routines you have to take care of your pet I will follow! I love taking pictures of my pets, so I can definitely take some of your animals too.


Noah H.
“Noah watched our dog for 9-10 days while we went to Florida. He took amazing care of him. He sent pictures frequently and even kept our house clean. He is a very responsible young man who loves animals. He also took care of our hamster and cat while we were away. I highly recommend him if you are looking for someone to watch your fur babies.”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 pet sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winchester on Rover as of Aug 2025 was about $18 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 10 pet sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Winchester.
Rover makes it easy to find Winchester pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 10 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
