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.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester pet sitters
These prices are per visit. Pricing may change based on the options you select. A booking fee of 11% and taxes will apply. Learn more
“Alexsys did an amazing job with my dog. She cared for her like she was her own and sent me plenty of updates. My dog was happy and well loved while we were out of town. Will definitely be booking with her in the future!”
“Mayahrissa is an excellent pet sitter. From our first meeting I could tell she really cares about animals and although I was a little nervous leaving my 3 month old puppy with a sitter for the first time, I immediately trusted Mayahrissa. During her visit, she followed all the care directions and sent me lots of pictures. My dog really likes her. She has a calm demeanor which puts pets at ease. I highly recommend her.”
“Kim did an amazing job with our Murphy. She’s so sweet and attentive to our pup, she took plenty of pics and gave lots of love during her visit. 10/10 recommend!!”
“Gabby gave live updates and took lots of photos of our babies. Great communicator and you can tell our pups enjoyed her company with the report card photos. Thanks again!”
“We were very pleased with Hannah! She was so prompt with her visits, sent detailed and informative communications regarding activity, sleeping, medicine, their walks, and took plenty of pics of our girlies. Everything worked like clockwork and went just fine. Thank you Hannah for loving on our girlies while we were gone!”
“Gary & Maryann took such wonderful care of our animals. They showed them all kindness and top notch care, and they gave us such peace of mind. They were so flexible and understanding, too! Thank you so much to Gary & Maryann. Would recommend you to someone in a heartbeat.”
“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.”
“Alexandria showed up to check in on my cats despite a winter storm! Very much appreciated!”
About: I’ve been caring for pets since I was a teenager. Whether it be my own dog or someone else’s, I love taking care of animals. In the past, I’ve spent extensive time caring for the pets of friends and neighbors along with my own. I work as a freelancer, so I can make my schedule work for any times! While I am available on weekends, I focus on M-F from 8am-8pm for pet sitting. With my own dog, I’m very protective and make sure she is safe and gets the care she needs. That is no different with other dogs. Whenever I’m watching a pet, I always make sure to keep them safe and give them the best time!
“Leigh was just fantastic with Patches, my special needs 3 yo American Bully! She was caring and kind, and helped with his wheelchair needs. I will rebook her anyday!”
“Steven showed up on time and even cleaned up a bit of a mess my dogs had made! Will definitely book again when I need a drop in!”
“Mya was phenomenal! She was right on time and very communicative! Def would use her again”
“Charissa gave me so much peace of mind while we were away! She cared for our pets while we were gone and sent meticulous, detailed updates each time she checked in with pictures and videos. I was a little nervous as Charissa was newer to Rover and didn’t have as many reviews as other sitters, but at our meet and greet I got a good feeling about her and I am so glad I chose her above others with more reviews. Highly recommend! Will use her services again for sure!”
About: 6 years of personal experience with an array of pets. My care is exceptional due to my profound love of fur and not so furry babies. I moved this January without my family fur baby and have all the time to take great care of yours! Currently just studying online and am home all the time. I don’t have a yard but I live less than a 1 min walk from Handley high school park which is HUGE and perfect for highly interactive walks!
About: I’ve had the joy of caring for pets of all ages—from bouncy puppies full of energy to gentle seniors who just need a slower pace. I’m patient and really tune in to each pet’s little quirks and needs. Shy or nervous pets especially warm my heart, and I love helping them feel safe enough to wag their whole bodies with happiness. Whether it’s giving meds, taking long walks, or simply being a calm, loving presence, I’m all about making your furry friend feel cozy, cared for, and truly loved. Hi, I’m Destini! I’m starting a new job, so my schedule is a little unpredictable right now. I’m still accepting bookings when I’m available — feel free to message me with your dates and I’ll let you know if it works! I do not offer pet care services in my own home, but I am fully available to care for your pet at your location or during walks. I focus on providing attentive, safe, and personalized care wherever your pet feels most comfortable.
About: I have taken care of Guinea pigs, cats, dogs, fish etc. I have worked with many different breeds and species of animals and an more than willing to learn something new. I have autoimmune disease so I don’t work a typical 9-5. But! That means I have more time to take care of your sweet little fur-babies! 😊 I will make sure your pup feels safe and loved while your are away. I can also check your mail and do some light house cleaning!
About: I have had cats and dogs ever since I was a baby. I grew up learning how to attend to an animal and give them all the love and care they need and more! I love animals with all my heart and I would be more than happy to care for yours! I have taken care of dogs of all ages and sizes. I also have experience trimming dog’s nails and giving them pill medication if needed. Neighbors and friends have trusted me many times with looking after their pets while they were away. I’m currently working part-time on specific days so my schedule is fairly set-in-stone. I am available on Fridays and weekends all day, then in the early mornings and evenings Mondays, Tuesdays, and Thursdays. I will care for your animal based on the instructions I’ll be given, and make sure they get all the care, love, and attention they want. I’ll create a trusting and comfortable relationship with your pet on their terms! Their comfortability and trust is what I’ll strive towards. I can keep them company and play with them for a little while, while also making sure they are taken care of!
“Alex was very professional & paid attention to detail. He was at out house when he was supposed to be and followed the directions I left for him. Next time we need someone to stop in we will definitely use him again!”
About: Hi my name is DaVion! Caring for others is second nature to me—whether it’s people or pets. I have hands-on experience with animals and truly enjoy spending time with them. I offer dog walking, feedings, drop-in visits, and fun playtime. I understand how important it is to have someone reliable and caring looking after your pet, and I’m happy to work around your schedule to make things easy and stress-free. Whether it’s an energetic pup or a laid-back senior pet, I’m here to give them the attention, affection, and care they deserve. Your pet’s comfort and safety are always my priority. Let me know how I can help! I am a full time college student. My schedule stays daily consistent and I am proactive about any changes Mon-Wed 3p-10p Thur 4:30p-10p Sat & Sun Appointment based I can come to your home and provide any pet care you may need! I am ok with any time of environment as long as there are directions
Loving pet sitters in your neighborhood
Search Results
Alexsys T.Star Sitter
“Alexsys did an amazing job with my dog. She cared for her like she was her own and sent me plenty of updates. My dog was happy and well loved while we were out of town. Will definitely be booking with her in the future!”
Myahrissa R.Star Sitter
“Mayahrissa is an excellent pet sitter. From our first meeting I could tell she really cares about animals and although I was a little nervous leaving my 3 month old puppy with a sitter for the first time, I immediately trusted Mayahrissa. During her visit, she followed all the care directions and sent me lots of pictures. My dog really likes her. She has a calm demeanor which puts pets at ease. I highly recommend her.”
Kimberly B.Star Sitter
“Kim did an amazing job with our Murphy. She’s so sweet and attentive to our pup, she took plenty of pics and gave lots of love during her visit. 10/10 recommend!!”
Gabby T.Star Sitter
“Gabby gave live updates and took lots of photos of our babies. Great communicator and you can tell our pups enjoyed her company with the report card photos. Thanks again!”
Hannah D.Star Sitter
“We were very pleased with Hannah! She was so prompt with her visits, sent detailed and informative communications regarding activity, sleeping, medicine, their walks, and took plenty of pics of our girlies. Everything worked like clockwork and went just fine. Thank you Hannah for loving on our girlies while we were gone!”
Gary & Maryann C.
“Gary & Maryann took such wonderful care of our animals. They showed them all kindness and top notch care, and they gave us such peace of mind. They were so flexible and understanding, too! Thank you so much to Gary & Maryann. Would recommend you to someone in a heartbeat.”
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.”
Alexandria Y.
“Alexandria showed up to check in on my cats despite a winter storm! Very much appreciated!”
Gabriel K.
“Gabriel is everything you would want from a pet sitter. Responsible, caring, reliable, playful, punctual, communicative, etc. I would Highly recommend him for any of your pet sitting needs. I will be using him again as I know many others will as well. So, book him now before he gets too busy!!!!”
Leigh P.
“Leigh was just fantastic with Patches, my special needs 3 yo American Bully! She was caring and kind, and helped with his wheelchair needs. I will rebook her anyday!”
Steven F.
“Steven showed up on time and even cleaned up a bit of a mess my dogs had made! Will definitely book again when I need a drop in!”
Mya R.
“Mya was phenomenal! She was right on time and very communicative! Def would use her again”
Charissa L.
“Charissa gave me so much peace of mind while we were away! She cared for our pets while we were gone and sent meticulous, detailed updates each time she checked in with pictures and videos. I was a little nervous as Charissa was newer to Rover and didn’t have as many reviews as other sitters, but at our meet and greet I got a good feeling about her and I am so glad I chose her above others with more reviews. Highly recommend! Will use her services again for sure!”
Lesly M.
About: 6 years of personal experience with an array of pets. My care is exceptional due to my profound love of fur and not so furry babies. I moved this January without my family fur baby and have all the time to take great care of yours! Currently just studying online and am home all the time. I don’t have a yard but I live less than a 1 min walk from Handley high school park which is HUGE and perfect for highly interactive walks!
Tearia B.
About: I’ve had the joy of caring for pets of all ages—from bouncy puppies full of energy to gentle seniors who just need a slower pace. I’m patient and really tune in to each pet’s little quirks and needs. Shy or nervous pets especially warm my heart, and I love helping them feel safe enough to wag their whole bodies with happiness. Whether it’s giving meds, taking long walks, or simply being a calm, loving presence, I’m all about making your furry friend feel cozy, cared for, and truly loved. Hi, I’m Destini! I’m starting a new job, so my schedule is a little unpredictable right now. I’m still accepting bookings when I’m available — feel free to message me with your dates and I’ll let you know if it works! I do not offer pet care services in my own home, but I am fully available to care for your pet at your location or during walks. I focus on providing attentive, safe, and personalized care wherever your pet feels most comfortable.
Mary M.
“Mary is amazing with animals!! She loves them. She has a dog of her own that she takes extremely good care of. My Ashton (who takes to nobody) took immediately to Mary. She’s the only one he’ll let pick him up and carry him. She’s patient, loving, knows an animal’s specific queues, is a great trainer, and I’d recommend her a thousand times over to watch your babies! She’s always on time and she always - ALWAYS makes time if I need her on the fly.”
Samantha S.
“I’m happy to recommend my friend for a dog walking position. She is incredibly hardworking, kind, smart, and responsible—qualities that make her a perfect fit for caring for animals. In school, she is dedicated and consistently performs above average, showing strong focus and commitment. As a pet owner herself, she takes excellent care of her cat, Tator Tot, who is well-loved, well-fed, and gets plenty of playtime. Her compassion and reliability extend to everyone around her, and I have no doubt she’ll treat every dog she walks with the same love and attention.”
Alex H.
“Alex was very professional & paid attention to detail. He was at out house when he was supposed to be and followed the directions I left for him. Next time we need someone to stop in we will definitely use him again!”
DaVion P.
About: Hi my name is DaVion! Caring for others is second nature to me—whether it’s people or pets. I have hands-on experience with animals and truly enjoy spending time with them. I offer dog walking, feedings, drop-in visits, and fun playtime. I understand how important it is to have someone reliable and caring looking after your pet, and I’m happy to work around your schedule to make things easy and stress-free. Whether it’s an energetic pup or a laid-back senior pet, I’m here to give them the attention, affection, and care they deserve. Your pet’s comfort and safety are always my priority. Let me know how I can help! I am a full time college student. My schedule stays daily consistent and I am proactive about any changes Mon-Wed 3p-10p Thur 4:30p-10p Sat & Sun Appointment based I can come to your home and provide any pet care you may need! I am ok with any time of environment as long as there are directions
Over 457 pet parents in Winchester have booked pet sitting
Winchester pet parents share their Rover experiences
Alexsys took wonderful care of our Penny and made our daughter feel very comfortable leaving her for the first time. She sent updates and pictures and made sure we knew Penny was doing well. We would absolutely request her again in the future.
Hannah was punctual, professional and provided a prompt and attentive service to our German Shepherd who can be a handful. We certainly appreciated her delivery, and highly recommend her to everyone looking for per care in the area.
I always have complete peace of mind when Kyla cares for my cat. She’s thorough, conscientious, and super caring. My cat loves her!
Leigh was just fantastic with Patches, my special needs 3 yo American Bully! She was caring and kind, and helped with his wheelchair needs. I will rebook her anyday!
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!
Ashley did a wonderful job, kept me informed and took excellent care of my kitty, Opal! Would absolutely hire her 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!
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 Jul 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 Jul 2025, there are 113 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, 86% 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 113 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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