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 for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Jenny did a great job with our Luna. She treated our girl like she would her own animals. We had her come let her out for a potty break and some playtime in the backyard. Our girl was tired so it was nice that Jenny didn’t force Luna to do anything. We look forward to booking Jenny to help us out on our long days away from home when Luna can’t be with us”

“Alanah took great care of our dog Hank, she was very communicative and our dog often tends to be quite anxious when we leave but he was happy and content when we arrived home. He was really comfortable with her coming to check on him. Thank you Alanah!”

About: I have been a devoted pet caregiver and self owner since the age of 10. I have experience training and care giving for many different type of breeds such as huskies , poodles , jack Russell’s, German shepherds, pit bulls , and more. I always have experience with cats as well and love them just as much. My passion for the genuine care of animals is immense and I would strive to give the best service always. I have been fortunate enough to take some time away from my 9-5 and have had a dire need to pick up a hobby of something I genuinely would LOVE to do. My schedule is completely open to the needs of fur babies! I have one extremely friendly and loving husky who would love to engage with other pets just as much as I would. I have a large fenced backyard for play and gates that block off any potential hazards such as a open road.
About: At age 16 I helped open up Homeland Pet hotel. I worked there 2 1/2 yrs. I was hooked. I have trained my dogs, my family and friends dogs and than helped with police K9s until I retired. I moved to Kentucky to work and be in an internship with a great training facility. In 2018 I moved back to California. I traveled and now I want to stay home and take care of or train your dogs. I take care and train all ages, size and breed of dogs. I have administered medications in all forms and I bath, brush and do nails. I am retired and I have the time and the means to help you and your pets have fun in life. I take my dogs to dog park and beach weekly when I am not camping. I am the person in my family everyone calls when they have a dog question. I am attentive, kind and playful, but I do have boundaries. I communicate very well with dogs and I'm pretty good with humans also. I have a 6 ft fence around my entire yard. I have my property sprayed for fleas and other critters every other month. It's a quarter acre property well maintained. I plenty of space inside for pets and I have several crates in all sizes if needed.
“Heather is absolutely amazing. She went above and beyond. She not only did everything we asked but did even more! She gave our cat so much love and attention! She sent amazing updates and photos. Do not hesitate to book Heather! She is absolutely pro and the best hands down!”


About: Im home 24/7 so you need a sitter dog, walker im there 😭 all I do currently is take care of 4 dogs. Always make sure they get their walk so they stay fit, I never over feed, make sure they get their outside play time and nap time I am on it. I currently have plenty of spare time so im very free everyday to go on walks, play take care of a dog whenever needed. Currently do that right now with my own little weiner army all I do all week is take care of dogs. I have 4 small weenies who love to dig and play in the big back yard and i take them on walks every day or every other day depending on their energy. They do mostly love to sleep throughout the whole day and dig.
“Ashleigh was so great with our 3 giant “puppies.” I loved having the daily reports and feedback. She caught the cutest photos of them too :) Highly recommend her services! Our doggos loved her. We will definitely request for her again.”

About: Hi I’m jen . I was a personal trainer , but I found my true passion in working with animals especially dogs !! I have a big yard to play in, and two very friendly little dogs . I’ll treat your dog like my own , because I know how difficult it is to leave your fur babies and feel at ease. I send tons of videos and pictures to make you feel they’re still with you while away ! Just give me all your concerns and I’ll do my best to make you worry less on your trip ! I’ve loved dogs since I was a kid and grew up on a ranch with many along with many other animals so I know how to take care of them . I’ve also recently been taking online vet tech courses just to have the extra knowledge in caring for your fur babies ! Seniors I’ll take extra caution and care because I know they’re fragile and need more loving . I do often sit 5+ at Once as long as they all get along and I feel social interaction is Great for dogs as well ! I hope to meet your furry kids soon ! Love ❤️ Jen I’m full time pet sitter so I’ll have all my time to focus on your pets needs .just text me anytime with any questions or concerns. I keep my place puppy proof and supervise 24:7 and cater to any needs your pups should have . Feel free to text or call anytime! I wake around 6-7 am and in bed around 10pm so I’ll try to work with you on your schedule because I do this full time. I have a fenced yard and extra crates if you prefer yours crated to eat or at night . Otherwise they’re welcome in my room .
“BreeAnna did an amazing job taking care of my 2 kitties. I was gone for a whole month and was worried about leaving my cats for so long for the first time but BreeAnna took such good care of them that I was able to relax and enjoy my time. She was very communicative and took great pictures every day so that I could see that my little ones were not just doing well but were also happy. She spent time playing with them and giving them cuddles. Thank you so much for everything you did to take care of Mochi and Shooky while I was gone!”

About: I have experience working with puppies and many breeds. I will reinforce desirable behaviors through positive reinforcement. I have experience giving medication. I can take your pet to the vet for you. I have many years of experience working with animals at a veterinary hospital and animal shelter/rescue. I am available short or long term. I am available week days and weekends. Caring for pets is my vocation. I don’t have any schedule restrictions I have enclosures for the pet and a larger enclosed yard. I provide opportunity for water loving dogs to play in the pet pool. I provide “nose work” for those dogs that need mental activities.

“Donna was absolutely perfect. I was in a pinch, so I decided to give Rover a look. Donna was 1 of several sitters in my area and reading thru her page, I saw her response time was only a few minutes, it was actually more like a few seconds. Since my back was against the wall, with something super important I need to get to, timing is everything. Her communication was spot on and she even arrived early to make sure that I was comfortable before I left. I dumped a bunch of information on her about my pup and she listened very well and made me feel comfortable enough within just a few minutes to walk out the door, leaving my house and my special dog in the hands of someone I just met. I wouldn't hesitate for one second, to recommend Donna to any of my family or friends or a stranger on the street. Thank you Donna, for taking care of my baby and rising to the occasion on such a short notice.”

About: I have been around animals my entire life and have volunteered at an animal shelter where I socialized puppies and cats. Animals have always been very comfortable around me and vice versa. I am comfortable with all sizes of dogs and breeds. I care very deeply for animals and would love to help you ensure your dogs are getting the exercise and attention they need. I graduated college with a major in veterinary technology at TJC, and currently work as a veterinary technician. I do have a full time job at a veterinary clinic with my days and hours varying. Typically I work 5 days a week with a max of 8 hours a day. Due to this I am unable to be with your pet at all times but would love to spend my free time with them! I make sure to stay in close proximity to the animal and keep a close eye on them while playing with toys to prevent any injury. I am very knowledge on what kinds of things are toxic to both cats and dogs and am able to pick up on signs of possible varying illnesses.
About: I’ve assisted with dog sitting alongside my mom and grandma, helping with playtime, and companionship. I’m patient, attentive, and following routines to ensure dogs feel safe and cared for. Pet care fits easily into my daily routine. I have flexible availability as I am unemployed and already care for my own two cats and two bearded dragons daily. I provide attentive care in peoples homes, following routines closely. As an owner of two cats and two bearded dragons, I’m experienced with safety, cleanliness, and gentle handling.
About: My name is Vicki. I am a 59 year old wife, mother, grandmother and animal lover. I have worked with Veterinarians over the years and have fantastic references. One of my best friends is a veterinarian. We have 2 dogs of our own (my hubby and I.) We spoil them rotten! I have an animal science degree and a HUGE compassionate heart. Animals are truly my heaven on earth. I am a responsible, loving and trustworthy pet companion. Why I love dog sitting: Since I was a child! I have grown up with pets and never been without an animal in my life. About my yard: Dog area, dog door to freely come in and out. I dedicate 100% of my time to your pet with love and compassion and exercise. You will have freedom to know your pet is well taken care of. My home is pet friendly and has a fenced area with a dog door. It is easy access to go in and out to go potty.
About: As a former D1 athlete, high performance, strict punctuality, and absolute accountability are built into my DNA. I bring that exact level of professional discipline to pet care, specializing in gentle, steady-paced fitness routines for senior or overweight dogs, as well as meticulous drop-in care for cats and small caged pets. My primary focus is keeping your home immaculate, respecting your privacy, and ensuring your animals stay safely on their familiar, veterinary-approved care schedules while you travel. While I specialize in senior care and pet wellness, I welcome healthy adult dogs, puppies, and pets of all shapes and sizes! For full transparency, my sweet baby accompanies me securely in a pack carrier on my daytime rounds. This setup naturally guarantees that I am providing a peaceful, quiet, and completely focused presence in your home, with no rushing through visits. I treat your property with executive-level respect and look forward to keeping your furry family members happy, healthy, and perfectly cared for! Pet care is a joyful, highly organized part of my day! Using the schedule discipline I built as an athlete, I reserve dedicated morning, midday, and afternoon windows entirely for my furry clients. Because my sweet baby is snuggled safely along for the ride, your pet receives my absolute undivided attention and a lot of extra love right on time! Inside your home, I provide customized, low-stress care tailored strictly to your pet's routine. For cats and small pets, this means precise feeding and pristine hygiene. For dogs, I prioritize safety by using your secure yard for active fetch or providing gentle, steady-paced neighborhood walks. For overnight stays, I bring executive-level respect to your property and peace of mind. My presence ensures a quiet, secure household where your pets receive consistent companionship, timely medication, and undivided attention right on schedule.
“Elise is amazing, she is basically Cain’s favorite person now… I’m pretty sure he likes her more than us 😅. Cain is living his best life, and I’m just grateful someone can handle his dramatic personality. Highly recommend! P.S. She takes the cutest picture updates.”

Over 152 pet parents in Winchester have booked pet sitting
Winchester pet parents share their Rover experiences
Sierra was absolutely amazing! We trusted her to care for our dog while we were away for a few days and she did not disappoint! She was kind, friendly and very easy to communicate with. She provided photos and updates each day which gave us the peace of mind that we needed. I would most definitely book with her again in the future!

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 $25
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 5 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 Jun 2026 was about $25 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 Jun 2026, there are 420 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, 88% of Winchester pet sitters respond in under an hour.
Pet sitters in Winchester have an average of 17 years of experience. 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 420 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 93% of pet sitters offer daily exercise, 93% offer medication administration, and 93% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. 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 background checks 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.




