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.
More resources
A focus on safety
Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect
Top rated Winchester pet sitters
“We're very thankful to have had Stacey's help this past week while we were on a trip! She did great with our cat's specific medicine instructions, and messaged us to try different methods when our cat wouldn't take it. She notified us when our cat was showing concerning signs in her health, took her to the vet for us, and made sure we were involved for every step when our girl's health grew serious. We're so glad Stacey was there were her to get early treatment when she needed it most! It's clear she truly cares about the pets in her care!”
“Darcee was fantastic! My dogs are not the easiest or the friendliest, so I’ve been hesitant in the past to hire a dog sitter, however, they warmed up to her very quickly. I was so relieved. Our boys were well cared for and we are so grateful we found her.”
“Awesome experience! I was busy on a trip so I didn’t have much time to communicate with Nik during the visits and he still sent very detailed check-in notes and made sure my girl was happy and healthy while I was out of town! I definitely recommend and will for sure use Nik for all future out of town visits!”
“Elizabeth is a very kind and flexible person and loves what she does! It's never easy leaving my babies with a stranger I've spoken to once or twice but Elizabeth made me very comforted and reassured that my babies would be in the very best hands. My kitties were happy and healthy when I came home. (And she's really good at taking pictures)”
“Lauren was great with my cat jewelzy. She did as I instructed and Jewelzy seemed happy. I appreciate Lauren picking up my mail and setting my trash out too. I will use Lauren again and likely soon. Thank you!”
About: I’m 24! I’m new to Rover but I have loved and taken care of animals since I can remember. Worked in Shelters. I have a dog of my own who is practically my kid. I’d love to meet and hangout with your fur babies! I currently have my own cleaning company. I don’t work everyday, and this sounds like the best thing to be doing when I am not cleaning! Animals bring me so much joy. I’d make sure they are as comfortable as I can make them! Keeping them busy is very important to me and making sure they feel safe.
“Amy is fantastic! She was able to help me out at the last minute when my plans had changed. She is always extremely thorough with her visits to my house. I really love how she takes pictures to show me that all my animals have been fed and she takes time to play with them and make sure they’re feeling happy. 100% I would recommend!!!”
About: I’ve been with dogs ever since I can remember. I grew up with cattle dogs and have lots of experience with dogs and cats as I foster often. I have a border collie pit mix and a Lab! I am able to help with medication administration, senior dogs, and puppies I am all for it! I’ve always been a pet lover. I currently work Monday-Wednesday. I am able to provide potty breaks during working hours. I’m home and available the rest of the week for lots of playtime and potty breaks😊. On my days off I love to go on walks with the pups and give the love and attention they deserve. We just built our house this year! I live on 2 acres and have part of it fenced. I have 2 fenced areas in the yard and dogs have access to water in both yards. I even have a room for my pups and others! My 2 sweet fur babies will be sure to keep your pups company. If I need to run an errand all dogs including mine will be crated for safety. I’m usually with my dogs at all times so they are in good hands with me! I DO REQUIRE IDENTIFICATION ON COLLARS.
About: Im very devoted to my furry friends. I got my first dog when I was 14. She is still with me today! I currently have 3 dogs and 2 cats. I’ve always been an animal lover, before I had a dog. It was all I ever asked for. My dad told me “anytime we asked what you wanted for your birthday or Christmas it was always a dog.” I am the type of person to stop and ask to pet peoples dogs! There all so cute. Im currently working part-time at a separate job on mondays and Tuesday, im free Wednesday - Sunday, im available for potty breaks, house sitting and dog walks! I will respect your house rules, I’m very courteous. I can help with potty training, or crate training if needed. Thank you for your time.
About: I’ve had pets my entire life and have always enjoyed taking care of them! I am very caring and will respect your pets needs! You won’t regret having someone dependable like me take care of your furry family. I work Monday through Friday 8-4:30. This leaves me available to stop by in the mornings on my way to work and also the evenings to give some much needed care! I am also fully available on the weekends to meet your needs. I am very attentive to pets and enjoy playing with them whether it be dangling a feather wand over my cats head while she jumps in the air to catch the feather, or playing fetch with my friends dogs!
About: I have grown up loving dogs and always had big and small ones! I have a 115 pound Pyranees Lab of my own and a pug! I come from a family that loves rescuing dogs and fostering! I am currently working part time as a barista in early mornings and am in highschool however am taking virtual College classes so I don’t have to be at the school. I love tennis and long walks and would love to spend time with pups! I would love to help and keep your pup company and loved and cared for!! I can come at any times needed and do whatever you need!
About: I have had my own dogs ranging from 10 lbs to 70 lbs for the last 15 years. I love fur babies of all ages. I am a teacher, so my summer hours are very flexible for vacationers! During the school year my evenings and weekend hours are pretty flexible. I have a very larger fenced yard. I have 3 friendly dogs and a large crate. My babies are okay with being outside if your baby likes to be alone without other dogs. I’m very respectful of the homes of other people and am aware that the dog may be very protective of their home and may need some time and patience to warm up to me.
“Kristi is a wonderful sitter! She took great care of my two pups and my home as well. We would love to have her back if we ever need a sitter again. She provided plenty of updates while I was away and was clearly very knowledgeable with dogs.”
Loving pet sitters in your neighborhood
Search Results
Keira M.
Star Sitter
“Keira did an excellent job taking care of our two dogs! She was prompt everyday and gave great updates to let us know how our boys were doing! Would highly recommend!”
Stacey F.Star Sitter
“We're very thankful to have had Stacey's help this past week while we were on a trip! She did great with our cat's specific medicine instructions, and messaged us to try different methods when our cat wouldn't take it. She notified us when our cat was showing concerning signs in her health, took her to the vet for us, and made sure we were involved for every step when our girl's health grew serious. We're so glad Stacey was there were her to get early treatment when she needed it most! It's clear she truly cares about the pets in her care!”
Darcee B.Star Sitter
“Darcee was fantastic! My dogs are not the easiest or the friendliest, so I’ve been hesitant in the past to hire a dog sitter, however, they warmed up to her very quickly. I was so relieved. Our boys were well cared for and we are so grateful we found her.”
Jamie W.Star Sitter
“First day with the pack. She did great!”
Nikki C.Star Sitter
“Awesome experience! I was busy on a trip so I didn’t have much time to communicate with Nik during the visits and he still sent very detailed check-in notes and made sure my girl was happy and healthy while I was out of town! I definitely recommend and will for sure use Nik for all future out of town visits!”
Diane A.
“Great communication and updates! Diane is very courteous too and great to work with.”
Elizabeth K.
“Elizabeth is a very kind and flexible person and loves what she does! It's never easy leaving my babies with a stranger I've spoken to once or twice but Elizabeth made me very comforted and reassured that my babies would be in the very best hands. My kitties were happy and healthy when I came home. (And she's really good at taking pictures)”
Lauren G.Star Sitter
“Lauren was great with my cat jewelzy. She did as I instructed and Jewelzy seemed happy. I appreciate Lauren picking up my mail and setting my trash out too. I will use Lauren again and likely soon. Thank you!”
Immajen B.
“Immajen is a caring and dependable dog sitter and walker. She’s great with animals and always makes sure they feel safe, happy, and well cared for. Anyone looking for someone trustworthy and kind to care for their dog would be lucky to have her!”
Amanda B.Star Sitter
“Amanda did a great job taking care of our two Beagle fur babies! We will definitely be booking her again! She did everything just as requested. Kenny and Sandy Sims”
Amy M.
“Amy is fantastic! She was able to help me out at the last minute when my plans had changed. She is always extremely thorough with her visits to my house. I really love how she takes pictures to show me that all my animals have been fed and she takes time to play with them and make sure they’re feeling happy. 100% I would recommend!!!”
Ryan R.
“Ryan was amazing! He was communicative, responded quickly and was more than happy to check on our pups while we were out of town. Next time we go somewhere, he will be our go-to!”
Elle S.
“Elle was great with my puppy! She was very attentive and made sure my puppy was well taken care of!”
Omni B.Star Sitter
“She did an excellent job followed everything i asked for and kept me updated with every visit will definitely be booking with her again! Thank you!”
Jessa C.
About: I’ve been with dogs ever since I can remember. I grew up with cattle dogs and have lots of experience with dogs and cats as I foster often. I have a border collie pit mix and a Lab! I am able to help with medication administration, senior dogs, and puppies I am all for it! I’ve always been a pet lover. I currently work Monday-Wednesday. I am able to provide potty breaks during working hours. I’m home and available the rest of the week for lots of playtime and potty breaks😊. On my days off I love to go on walks with the pups and give the love and attention they deserve. We just built our house this year! I live on 2 acres and have part of it fenced. I have 2 fenced areas in the yard and dogs have access to water in both yards. I even have a room for my pups and others! My 2 sweet fur babies will be sure to keep your pups company. If I need to run an errand all dogs including mine will be crated for safety. I’m usually with my dogs at all times so they are in good hands with me! I DO REQUIRE IDENTIFICATION ON COLLARS.
Ashlynn F.
“Ashlynn is just beloved by the many dogs she cares for specially my boy Fido. Dogs love her so much she once saved a strangers dog running wild on nyc streets with her loving and endearing voice alone . She's like a dog whisperer !”
Emily H.
About: I’ve had pets my entire life and have always enjoyed taking care of them! I am very caring and will respect your pets needs! You won’t regret having someone dependable like me take care of your furry family. I work Monday through Friday 8-4:30. This leaves me available to stop by in the mornings on my way to work and also the evenings to give some much needed care! I am also fully available on the weekends to meet your needs. I am very attentive to pets and enjoy playing with them whether it be dangling a feather wand over my cats head while she jumps in the air to catch the feather, or playing fetch with my friends dogs!
Ariel G.
“Ariel has been our go-to for over a year! We adore her, and so does our dog, Meredith. We can travel knowing that our sweet puppy is in the best hands and having the time of her life.”
Kasey K.
“If you’re looking for someone to love your pets like they’re royalty (or, honestly, better than most people love their actual children), Kasey is your girl. She has a full on zoo/farm situation going on at home. She has dogs, cats, birds, chickens, fish, lizards and maybe a few squirrels she’s secretly rehabilitating, and every single one of them is her baby. I’m pretty sure her first emergency contact is her vet. Kasey will literally try to rescue every animal she sees. Injured pigeon on the sidewalk? She’s on it. Random stray that clearly belongs to someone else? She’s already got a leash. Even if the animal bites her and she’s bleeding out, she’s still like, “It’s not his fault, he’s just scared!” Watching a movie with her is an emotional rollercoaster, not because of the plot, but because she’s devastated if any animal gets hurt. But seriously, she’s the most responsible and loving pet mom you could ask for. She keeps up with medications, vet visits, and about 400 different feeding schedules. Your pets are in the absolute best hands with Kasey, and she’ll probably love them more than you do. (Just kidding… kind of.)”
Kristi E.
“Kristi is a wonderful sitter! She took great care of my two pups and my home as well. We would love to have her back if we ever need a sitter again. She provided plenty of updates while I was away and was clearly very knowledgeable with dogs.”
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 pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. 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?
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 pet 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.
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 $20 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 120 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, 90% of Winchester pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 5 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 120 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.
Connect anywhere with the Rover app
