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
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Alexsys took wonderful care of our two cats while we were on vacation. She went above and beyond, and we’ll definitely book her again! We can’t recommend her highly enough!”
“Hannah was a life saver - she made what could have been a very stressful day the exact opposite. She dropped in twice to keep my dogs company while I spent the day at the office. She sent updates so I knew they were happy and taken care of. I know I won’t need to worry the next time I need to leave them alone for a day. This was my first time trying Rover, and I’ll definitely be using it again!”
“Kimberly was WONDERFUL to our two boys when we went on vacation. She really went above and beyond to get to know them, spend time with them, and make them comfortable. Our kitties usually are very skittish with people they don't know but they warmed up to her pretty quickly. She updated me everyday on how they were doing and I could tell she enjoyed them at least as much as we do :) She took time and put a special touch on each visit, even letting us know when packages arrived. We'd have Kim back anytime to watch our two kitties. They miss her already!”
“Gary & Maryann are wonderful with my 2 month old puppy! They were extremely understanding and flexible when we had a mishap causing us to have to change the time of our scheduled visit. They send pictures and let me know how she was during their visit. I know she’s in good hands with them! Thank you both so much!”
“Kathy was so responsive and reliable! She took great care of our dog and gave detailed info as well as pictures after all of her visits! we will definitely use her again ☺️”
“We booked Katie last minute and she was a God send. She was very sweet and awesome for our two cats and Riley our dog. She was even flexible enough to do longer had we needed her. I was very confident that my pets were in great hands. We will definitely book with her again.”
“Charissa is amazing! Our plans changed more than once and she stayed flexible working with us. We received beautiful pictures of all our dogs and updates for every visit. Her rates were very fair and she even cleaned up without being asked! We will be recommending her services to family and friends while also asking her back to our home. We love her and our pups do too!”
“Kyla is the best cat sitter! She must be a cat whisperer because she’s gained the trust of my anti-social cat! Kyla’s great at sending cute pictures and updates of my babies so I know they’re doing well when I’m away. Abbot, Mudpie, and myself all are so grateful for Kyla!”
About: I've trained dogs in my teenage years, and l've over puppies and kittens as well as lizards let me care for your pets while you relax. We’re a very organized couple and that allows us to have a well put together schedule. willing to always be flexible and tend to our pets easily! We have a dog park that’s a lovely drive away from the house! We love to play, take naps and match the pets moods and let them enjoy being themselves comfortably! And pet safety is a big deal! No wandering off and no biting or getting bitten of course haha
“Emily is a great pet sitter! I felt so happy knowing my cat, Lenny, was in good hands. She let me know he was safe and sound the entire time I was gone and also let me know everything important going on pertaining to his health & well being. 10/10 recommend!”
“DaVion was a kind and gentle handler of my special needs 3yo American Bully. He was responsible, arriving on time, and helped us with ease. He is generous and listens carefully, goes above and beyond. I’ll definitely be contacting him for my Rover needs again!”
About: Hi there! I’m Cassie — a lifelong animal lover and proud pet parent to two rescue pups. I’ve cared for animals since childhood, from dogs and cats to ferrets and guinea pigs, and providing loving, attentive care has always come naturally to me. I have hands-on experience with senior pets, administering medications (including insulin injections), and supporting dogs with complex medical needs like heartworms. I work part-time as a counselor at a crisis care center, which means I have plenty of extra time and flexibility to devote to your pet. I also carry a fully stocked pet first aid kit with me at all times, just in case. In my free time, I enjoy writing and traveling. I’m currently offering low rates as I get started on Rover because I truly love what I do — and I’d be honored to care for your pet like they’re my own. Pet care fits easily into my week! I work part-time and have a pretty flexible schedule, so I’m able to give pets lots of attention and time. Whether I’m caring for pets in my home or yours, their safety and comfort are my top priorities. I create a calm, pet-friendly environment and always follow your pet’s routine closely. I respect boundaries, monitor behavior, and provide lots of love and attention — just like I do with my own dogs.
About: Hi, I'm Audrey I'm a lifelong dog lover with two family pups — Elvis, a 3 year old Italian Mastiff, and Bella, a 13 year old sweet senior Shih Tzu-Maltese mix. I'm experienced with both energetic puppies and older dogs who need a gentler touch. Whether your dog loves long walks or slow strolls, I’m here to give them the care and attention they deserve! I work part time, so my schedule is flexible. I am available for drop ins, and walks throughout the day. I’m here to give your pup company or playtime! I do not have capability to board dogs. I offer drop ins, and routine walks that fit your schedule. I am able to give medications, food & treats, and extra love!
About: I have always had a deep respect for dogs, particularly for their intelligence, loyalty, and the meaningful connections they form with people. I previously had a miniature Jack Russell Terrier named Peggy Sue, who was an exceptionally affectionate and social companion. She greeted everyone she met with warmth and enthusiasm, which left a lasting impression on me. I'm genuinely looking forward to meeting your dogs, getting to know their individual personalities, and building a strong and trusting bond with them. For years I would bathe our dog, take her for long walks & to the vet, even to Petco because she loved to walk around the store after being groomed! We would pick out a toy and get her some treats for being such a good girl. She also loved to cuddle at night time & would curl up right below my legs, under the blankets. In her later age, I would help to clean up pee pads as unfortunately, her bladder didn’t function the same in her older age. During her last days I helped to make her feel comfort and to know that she was very loved and always will be. She is still always on our minds & in our hearts today. I’m currently available most of the time, the only time I wouldn’t be available would be on Sunday-Wednesday from 6am-7am and 9pm-10pm. I’m available all other days at any time & I’m available Sunday-Wednesday during any of the times not mentioned above. I would be more than glad to follow any instructions that you leave for me and you can feel free to contact me at anytime to check on your fur baby during their time with me for updates! I want you and your pet to feel safe and cared for and I hope to create a great bond with them as well.
Loving pet sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Alexsys T.Star Sitter
“Alexsys took wonderful care of our two cats while we were on vacation. She went above and beyond, and we’ll definitely book her again! We can’t recommend her highly enough!”
Hannah D.Star Sitter
“Hannah was a life saver - she made what could have been a very stressful day the exact opposite. She dropped in twice to keep my dogs company while I spent the day at the office. She sent updates so I knew they were happy and taken care of. I know I won’t need to worry the next time I need to leave them alone for a day. This was my first time trying Rover, and I’ll definitely be using it again!”
Kimberly B.Star Sitter
“Kimberly was WONDERFUL to our two boys when we went on vacation. She really went above and beyond to get to know them, spend time with them, and make them comfortable. Our kitties usually are very skittish with people they don't know but they warmed up to her pretty quickly. She updated me everyday on how they were doing and I could tell she enjoyed them at least as much as we do :) She took time and put a special touch on each visit, even letting us know when packages arrived. We'd have Kim back anytime to watch our two kitties. They miss her already!”
Gary & Maryann C.
“Gary & Maryann are wonderful with my 2 month old puppy! They were extremely understanding and flexible when we had a mishap causing us to have to change the time of our scheduled visit. They send pictures and let me know how she was during their visit. I know she’s in good hands with them! Thank you both so much!”
Kathy G.Star Sitter
“Kathy was so responsive and reliable! She took great care of our dog and gave detailed info as well as pictures after all of her visits! we will definitely use her again ☺️”
Katie R.
“We booked Katie last minute and she was a God send. She was very sweet and awesome for our two cats and Riley our dog. She was even flexible enough to do longer had we needed her. I was very confident that my pets were in great hands. We will definitely book with her again.”
Madilyn P.
“Great communication! Madi was a pleasure to have watch our dog and cats while we were away. Will use again.”
Charissa L.
“Charissa is amazing! Our plans changed more than once and she stayed flexible working with us. We received beautiful pictures of all our dogs and updates for every visit. Her rates were very fair and she even cleaned up without being asked! We will be recommending her services to family and friends while also asking her back to our home. We love her and our pups do too!”
Lisette R.
“She did an excellent job with my two cats! I can tell they were well taken care of and were just as happy as I left them! No messes either, which was a first!”
Gabriel K.
“Gabriel it’s fantastic! Communication went so well and he is very efficient. Super recommended.”
Kyla P.Star Sitter
“Kyla is the best cat sitter! She must be a cat whisperer because she’s gained the trust of my anti-social cat! Kyla’s great at sending cute pictures and updates of my babies so I know they’re doing well when I’m away. Abbot, Mudpie, and myself all are so grateful for Kyla!”
Sierra B.
“Awesome communication and taking care of our pup!”
Christopher P.
About: I've trained dogs in my teenage years, and l've over puppies and kittens as well as lizards let me care for your pets while you relax. We’re a very organized couple and that allows us to have a well put together schedule. willing to always be flexible and tend to our pets easily! We have a dog park that’s a lovely drive away from the house! We love to play, take naps and match the pets moods and let them enjoy being themselves comfortably! And pet safety is a big deal! No wandering off and no biting or getting bitten of course haha
Alex M.
“Alex was great while dropping in on my dogs. She went above and beyond what was asked and the pups loved her.”
Mya R.
“Mya is a great help and takes the best photos!”
Emily J.
“Emily is a great pet sitter! I felt so happy knowing my cat, Lenny, was in good hands. She let me know he was safe and sound the entire time I was gone and also let me know everything important going on pertaining to his health & well being. 10/10 recommend!”
DaVion P.
“DaVion was a kind and gentle handler of my special needs 3yo American Bully. He was responsible, arriving on time, and helped us with ease. He is generous and listens carefully, goes above and beyond. I’ll definitely be contacting him for my Rover needs again!”
Cassie J.
“I have known Cassie for nearly 10 years as a colleague, and one thing that’s always stood out is her deep love for animals. She watched my pup, Hops, while I was on vacation, and I couldn’t have felt more at ease. Cassie is incredibly responsible and reliable—I had zero concerns while I was away. Hops was well cared for, and I’d absolutely trust her to pet sit again.”
Audrey B.
“I can’t recommend Audrey B. enough as a pet sitter and dog walker! She is one of the most compassionate, responsible, and attentive people I know—especially when it comes to animals. Audrey has a natural ability to connect with pets and treat them like family. Whether it’s a playful pup or a shy senior cat, she’s always patient, gentle, and tuned in to their needs. I’ve seen firsthand how much love and care she puts into every interaction, from long walks to cuddles on the couch. She’s the kind of person who notices the little things—if your dog seems a little off or your cat needs some extra attention, Audrey will catch it and respond with care. Plus, she’s incredibly reliable and communicative, so you’ll always know your pet is in safe hands. If you’re looking for someone to care for your pet like you would, Audrey is absolutely the one to call. Your furry family members will be in the best hands!”
Breanna W.
About: I have always had a deep respect for dogs, particularly for their intelligence, loyalty, and the meaningful connections they form with people. I previously had a miniature Jack Russell Terrier named Peggy Sue, who was an exceptionally affectionate and social companion. She greeted everyone she met with warmth and enthusiasm, which left a lasting impression on me. I'm genuinely looking forward to meeting your dogs, getting to know their individual personalities, and building a strong and trusting bond with them. For years I would bathe our dog, take her for long walks & to the vet, even to Petco because she loved to walk around the store after being groomed! We would pick out a toy and get her some treats for being such a good girl. She also loved to cuddle at night time & would curl up right below my legs, under the blankets. In her later age, I would help to clean up pee pads as unfortunately, her bladder didn’t function the same in her older age. During her last days I helped to make her feel comfort and to know that she was very loved and always will be. She is still always on our minds & in our hearts today. I’m currently available most of the time, the only time I wouldn’t be available would be on Sunday-Wednesday from 6am-7am and 9pm-10pm. I’m available all other days at any time & I’m available Sunday-Wednesday during any of the times not mentioned above. I would be more than glad to follow any instructions that you leave for me and you can feel free to contact me at anytime to check on your fur baby during their time with me for updates! I want you and your pet to feel safe and cared for and I hope to create a great bond with them as well.
Over 464 pet parents in Winchester have booked pet sitting
Winchester pet parents share their Rover experiences
Kathy did a great job with my disabled 3 yo American Bully. He took to her right away and didn’t mind her putting on his harness and putting him in his quad wheelchair/cart. She also cleaned his area and a space nearby and took out the garbage, going above and beyond! I’m definitely booking her again and again!
Gabe did an excellent job caring for our two cats while we were away! One of them requires insulin injections and has a few quirks, and Gabe handled everything with confidence and care. He clearly paid attention during the meet and greet and followed instructions closely. Communication was great, and we felt totally at ease knowing they were in good hands. We’d happily book with Gabe again!
Popular requests near you
Select a filter and find qualifying Winchester sitters!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!
The median cost per night for pet sitting in Winchester is $20
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.
Sitters in Winchester average 4 repeat pet sitting clients
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 117 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 4 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 117 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.
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