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

“I absolutely love how caring she is. I was nervous at first because this is my first time using the app and she had to travel quite a distance to let my dog out but she took such good care of her. My dog is very friendly and generally loves all people, but I could tell she was happier than normal when I came home from work. Thank you for your care”


“Gemma did drop in visits daily for my puppy until she got fully vaccinated and I couldn’t recommend her enough! Will definitely get in touch with her again in the future if needed. Thank you!!”


About: I’ve had dogs my entire life and genuinely consider them family. I’m so dedicated to animals that I’ve chosen a pet-focused lifestyle over having children. As a husky mom and lifelong animal lover, I have hands-on experience with everything from energetic puppies to senior pets with special needs. I’m a certified pharmacy technician (CPhT), so I’m trained in medication safety and certified to administer vaccines—giving me an extra level of skill when caring for pets who need meds or special attention. I’m calm under pressure, detail-oriented, and treat every pet like they’re one of my own. I have very open availability and can easily fit pet care into my daily routine. As a husky mom, I’m accustomed to regular walks and consistent care, so whether it’s quick visits, daily check-ins, or overnight stays, I’m flexible and reliable. I’m attentive to your pet’s individual needs and always treat them with the same care and love I give my own. I prioritize safety and comfort above all else when caring for pets. In my home, I maintain a clean, secure, and calm environment where pets can feel relaxed and happy. I’m experienced with managing multiple pets, making sure each one gets individual attention while preventing stress or conflict. When caring for pets in their own home, I respect your space and routines, following all instructions closely to ensure consistency and comfort. I’m fully attentive, keep an eye on any health or behavior changes, and communicate promptly with you for peace of mind.

“Dina was fantastic! She gave me the peace of mind that I needed to enjoy my trip. I looked forward to each update, and I knew that my cats were in good hands with her.”


“Had to stay an extra day because of a plane cancellation and it was no problem for her. Also she had no problem putting eyedrops into my cat's eye. Great Job”



“Lindsey was great with our fur babies once again!! She has a very flexible shedule and I was at peace on my trip knowing that my babies were being taken care of good. I will definitely book her again in the future. Thank you so much! 😊”


“Chelsea was very responsive when I booked the drop-in and came a day early for a meet and greet. Ellie loved her! I loved getting pictures of her while I was at work. 😊”


“100% above and beyond!! Due to the hiccups of moving into a new house, my spouse latched all the security latches on the doors that we gave Allie the key to. So when she got to our house (and we had already flown hundreds of miles), she was unable to get in. We called a locksmith and Allie met them at our house so they could get her in. We were so grateful because otherwise we would have had to cancel our entire trip (business trip for a course). In addition, our critters were on their worst behavior including peeing and pooping in the kennels. Allie spent extra time with them since we figured they must have been stressing out, between the move, having the house “broken into,” and us being gone. She definitely treated our critters like her own! Definitely would use her services again in the future! Thanks Allie, you’re a rockstar!!!!!!!”


About: I have a wide array of experience with dogs from puppies of less than a year old to older aged dogs. I also have experience with all sorts of breeds (beagles, huskies, yorkies, etc). I have dog sat for family members and friends countless times and absolutely love them as if they were my own. I just started my summer break for college! I have two in-seat courses this summer on my campus every day of the week until 5 pm, so I will be available on weekends to look after your beloved pups! I can give your pet lots of love and attention. I can crate them easily if needed, and make sure they are getting plenty of walks. I will make sure any accidents are completely cleaned up, if there are any.

“Second time having Kristen watch my Karma girl and I just know she was very well taken care of!”


About: I have experience with horses, dogs, cats, and even reptiles. I have specialized experience with large animals, disabled animals and elderly animals as well. I have a genuine passion for animals and I am committed to providing personalized care. I go beyond just feeding and walking. I take the time to understand each pet's unique needs and personalities. I will ensure your pet will feel loved, secure and at ease while you're away. I go to college at the University of Kentucky during the day but the longest day I have will end at 5 on Mondays and Wednesdays. I am a Vocal Performance major so I do have performances every so often but they are very easy to work around. I provide personalized care designed to meet the unique needs of your beloved companions. I can care for pets of all shapes and sizes including daily walking, feeding, medication administration, and playtime. I can spend the night and leave your home in the same way I arrived and leave your pet just as happy as when you left!

About: **if looking for pet sitting, make sure your furry friend is good with small dogs and cats** I, myself, am a small business owner. I work in photography and know my schedule well in advance. I have a 1.5 year old pug (behaved and potty trained). He no longer needs a crate but he has his own bedroom for if he gets too overstimulated and wants to play rough. He’s never hurt a fly though! I also have a cat who I’ve had for 7 years. He is social and talks more than any human I’ve met. He stays to himself and lounges on his cat tree or explores my fenced in yard. My yard is protected 100% around at approximately 10 ft high surrounding. I have grass to play in that is regularly maintained. Both of my pets are up to date on shots and flea, tick, and heart worm prevented monthly. I had rescued a pug before my current one who passed away unfortunately but I was on a 24 hour schedule with his medications and had hospice available at all times. My current dog gets eye medications every morning due to a genetic issue. So I have experience with medication. As well as IV medication/fluids. I grew up on a farm in Kentucky and took care of everything from cattle to goats to chickens to cats and dogs. I was going to become a dog foster but decided this route first with the possibility of still doing that in the future! I also took care of people with disabilities as an aid during my early 20’s (I’m 31) so no poo poo, pee pee, or throwing up bothers my stomach at all! My goal is to make your pet feel at as home as possible and as stimulated as they want to be to keep from being sad when away from their parent(s). Whenever I’ve had to leave my pets for personal family circumstances in Kentucky, it broke my heart that they’d miss me. I also have a furbo. I will be happy to provide you a link that you may access. You can see them and throw them treats (if they’re allowed them). I’m also lgbtq+ to be clear of my personal orientation/gender. I love animals more than people and for better or worse, that’s the truth :) I book my shoots with brands and talent way in advance. It makes it very easy to plan! I also will volunteer passing out clothes and food to those without shelter but I also plan that a month in advance and make my own schedule! I can crate your dog if needed. I just ask you bring your crate. As listed before, I have a playful pug and a lazy cat. I’m able to give medications and have a lot of experience with that!

“Maria did an excellent job with two very hard headed dogs! We appreciated her very much!”

About: I simply love dogs!! They are my passion! I love English Bulldogs, French Bulldogs, Lhasa Apsos, Shihtzus, Shorkies, Greyhound’s, King Charles Caviler Spaniels. I know a lot about these breeds and they’re my speciality. Excited to love on other breeds too. This is my way to love on all these doggies since I cannot be a full time fur mommy to them all. My fur babies in my home are Khalessi (English Bulldog girl). My Lhasa Apso passed away August 2023. My Shorkie is still in the family, rehomed with an older family member for emotional support. I have been raised with dogs my whole life. One of my goals is to get some bulldog hugs! 😉 I’m also a MidWoof. I have independently and successfully delivered 3 litters of puppies in my home. Then whelped (nursed and raised) one litter til they were 4 weeks old of age then found their furever homes. I will love on your fur babies like they’re my own. It takes a special love to understand the high maintenance needs of bulldogs. I’m your girl for that! BOOK ME! Looking forward to being your Fur Baby’s Bonus Mom when they’re in my care. *I also have 10+ repeat clients not listed on this app. I currently work from home full time and I’m a mom to young kids. I could do drop in visits during the day. On weekends, when I’m in town, I could be fully available to dog sit in your home, my home or for check in visits. I have plenty of grassy court yard space where I live in a dog friendly neighborhood. I also have a fur baby to keep your dogs company if needed for service in my home. I have a dog room set up in my home. We also travel to dog parks when weather permits, if your dog needs activities, we will go on walks and even to our favorite dog park!

“Laura was great, I had her let out one of my fur kids and she was flexible when I needed to push something a little and sent pictures so got to see the kiddo some during the day. She also did the simple but important little things like making sure he had water which I appreciated.”


“Miranda did Great. She showed up last minute. Took care of Our Babies Highly Recommend”


“Great experience! Cheyanne done a drop in visit for my 4 cats while we were out of town for Thanksgiving. She sent pictures to me when she dropped in which gave me peace of mind knowing everything was ok. She fed them and cleaned out the litter boxes. Will definitely be booking again”


About: I have been dogsitting for over 5 years. The clients I have worked for I have done overnight stays, dog walks, and day sitting for up to 8-10 hours. I do have one dog I sit for that doesn’t do walks so I adjust to what the clients needs. On overnight stays, I do clean up and bring in mail/ newspaper if the clients ask. I am a big animal lover so your dog/ cat will get lots of love. I do have a clients that likes to receive pictures during my stay. The dog will get plenty of exercise and playtime. Also I am flexible and very reliable. I can provide references of my regulars if needed and their type of dog. I enjoy providing lots of fun and love. I am flexible and reliable. I am able to meet to whatever the client might need. I am available whatever day and time. I do my best to meet the needs of the client. I haven’t cared for other animals in my home besides my own. When I go to someone’s residence, I follow what the owner normally does. I am usually left instructions to follow.

About: I am a huge animal person! I have a special interest in feline care, and currently working with a bunch of feral community cats, as well as volunteering at animal shelters with both cats and dogs. I have grown up around all kinds of animals, and currently have 2 dogs and a cat. I’m currently a college student looking for employment, so my schedule is pretty open! I’m free to hang out with your pets any time right now! I have a fenced in yard, and multiple rooms to seperate and rotate if needed. My dogs are friendly, and my cat will keep her distance, likely staying in my room.

About: Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching taking care of animals since I was a kid and I just love it I absolutely love taking care of your fur babies! Their schedule is totally accustomed to your needs and wants as their owners if you create a schedule for them, that would be wonderful and allow me to take care of your fur babies as you would yourself I do services in Lexington and Winchester, I’m currently working full-time with my hours ranging from 6 AM to 4 PM 5 days out of the week! Hours may vary depending on work Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching taking care of animals since I was a kid and I just love it! I don’t offer boardings at the moment but I would love to housesit or do drop-in visits for you!
Loving pet sitters in your neighborhood
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Kris R.Star Sitter

“I absolutely love how caring she is. I was nervous at first because this is my first time using the app and she had to travel quite a distance to let my dog out but she took such good care of her. My dog is very friendly and generally loves all people, but I could tell she was happier than normal when I came home from work. Thank you for your care”


Gemma B.

“Gemma did drop in visits daily for my puppy until she got fully vaccinated and I couldn’t recommend her enough! Will definitely get in touch with her again in the future if needed. Thank you!!”


Lauren I.
“Lauren is such a loving and responsible dog mom to her huskies and has been wonderful as a pet sitter for our family. I trust her with my 2 senior cats while I'm away and am happy to have such a caring person to love on them in my absence. She even sends picture updates so I know my cats are doing great.”


Dina J.Star Sitter

“Dina was fantastic! She gave me the peace of mind that I needed to enjoy my trip. I looked forward to each update, and I knew that my cats were in good hands with her.”


Kayla C.Star Sitter

“Had to stay an extra day because of a plane cancellation and it was no problem for her. Also she had no problem putting eyedrops into my cat's eye. Great Job”




Lindsey B.

“Lindsey was great with our fur babies once again!! She has a very flexible shedule and I was at peace on my trip knowing that my babies were being taken care of good. I will definitely book her again in the future. Thank you so much! 😊”


Chelsea D.

“Chelsea was very responsive when I booked the drop-in and came a day early for a meet and greet. Ellie loved her! I loved getting pictures of her while I was at work. 😊”


Allie H.Star Sitter

“100% above and beyond!! Due to the hiccups of moving into a new house, my spouse latched all the security latches on the doors that we gave Allie the key to. So when she got to our house (and we had already flown hundreds of miles), she was unable to get in. We called a locksmith and Allie met them at our house so they could get her in. We were so grateful because otherwise we would have had to cancel our entire trip (business trip for a course). In addition, our critters were on their worst behavior including peeing and pooping in the kennels. Allie spent extra time with them since we figured they must have been stressing out, between the move, having the house “broken into,” and us being gone. She definitely treated our critters like her own! Definitely would use her services again in the future! Thanks Allie, you’re a rockstar!!!!!!!”


Carly P.
“Carly is an amazing caregiver of all furry creatures. She has watched our Roxy on numerous occasions and she treated her like she was her own dog. She’s very reliable and goes above and beyond.”


Kristen S.

“Second time having Kristen watch my Karma girl and I just know she was very well taken care of!”


Courtlin C.
“Courtlin is amazing! I’ve dog sat with her several times and she does a wonderful job. She is careful not to leave a mess. She’s good about cleaning up, turning the lights off, and leaving the house better than she found it. She’s great with pet’s. She’s very responsible and has watched up to five dogs at a time and made sure to spend time with each of them and keep them entertained. She’s responsible and reliable and if you need her she’s great at responding. I’d trust her with my pet’s whenever I needed her and have referred her to my friends who have needed help with dog sitting!”


Eden E.
“Eden is a caring and responsible pet owner, I would trust him with my own pets! He has a great love for animals, and his dog and cat are happily cared for.”


Maria L.
“Maria did an excellent job with two very hard headed dogs! We appreciated her very much!”


Ebony H.
“Ebony is hand down the most compassionate animal lover I have ever witnessed!!! She will love your animal just as if they are her own! Ebony is well educated and is a great person to have in your corner, especially if you need help with just simple questions about animal that you may need help with! She has the answers, and is an amazing Dog Consultant! She is dedicated to her services and is willing to open up her home at anytime and will cultivate it to your dogs new oasis and a true home away from home! She will accommodate each and everyone of yours and your dogs needs to make sure that your animal’s stay feels just like home! I will definitely be booking with Ebony again for my future dog sitting needs! She calls herself your animals “Bonus Fur Mom!” And it’s so true…and she will stand by it!! Book with her today! I promise you won’t be sorry! :)”


Laura S.

“Laura was great, I had her let out one of my fur kids and she was flexible when I needed to push something a little and sent pictures so got to see the kiddo some during the day. She also did the simple but important little things like making sure he had water which I appreciated.”


Miranda K.

“Miranda did Great. She showed up last minute. Took care of Our Babies Highly Recommend”


Cheyanne R.

“Great experience! Cheyanne done a drop in visit for my 4 cats while we were out of town for Thanksgiving. She sent pictures to me when she dropped in which gave me peace of mind knowing everything was ok. She fed them and cleaned out the litter boxes. Will definitely be booking again”


Pam D.
“Pam has been my pet sitter for years. She does an excellent job, and my pets love her. She is extremely trustworthy, and always leaves my home in excellent shape. Highly recommended!”


Ashlynn S.
About: I am a huge animal person! I have a special interest in feline care, and currently working with a bunch of feral community cats, as well as volunteering at animal shelters with both cats and dogs. I have grown up around all kinds of animals, and currently have 2 dogs and a cat. I’m currently a college student looking for employment, so my schedule is pretty open! I’m free to hang out with your pets any time right now! I have a fenced in yard, and multiple rooms to seperate and rotate if needed. My dogs are friendly, and my cat will keep her distance, likely staying in my room.


Sara W.
“Sara is absolutely amazing with my dog Fizzie! She will love your pets as if they were her own! She is kind hearted and hard working, and I cannot recommend her more for your pet needs!”
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
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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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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 146 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, 93% of Winchester pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters 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 146 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.
