Pet Sitting Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 154 pet parents in Winchester have booked pet sitting
Winchester, Find top rated pet sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Thank you so much for dropping in and caring for nova when I’m away! Makes my life less stressful knowing I have someone looking out for my little pup. She is so happy when you’re around !!”
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.
“Thank you, Ricki for such good care of my two cats while I was on vacation. The photos each day were great and I could see how well you were caring for them. I arrived home to very happy and healthy cats. Much appreciated.”
“Heather was incredibly professional, kind, and patient with my dog CJ. He’s a large dog and can be cautious when meeting new people, and she did a great job reading his comfort level and building trust at his pace instead of forcing interaction. During our meet and greet, she was knowledgeable, realistic, and very aware of dog behavior, which immediately made me feel more comfortable. You can tell she genuinely cares about the animals she works with. Overall it was a lovely experience, and I would absolutely book with her again.”
“Ramey was wonderful! I really appreciated that she did a meet and greet beforehand, which helped me feel confident and at ease leaving my cats in her care. She was also very responsive and communicative throughout, giving me updates and making sure everything was going smoothly. Highly recommend her to anyone looking for a reliable and caring pet sitter! I will be using her from now on whenever I am out of town.”
“Our babies did so good with Estefany! She was prompt and thoughtful with her visits, sending us great photos letting us know the kitties were good to go. We’re very thankful! ❤️”
“Lucas was great with our 12-year old, feisty girl! He took great care of Janis while we were away for 10 days. He communicated well, and was a pleasure to work with. Lucas was the right fit and we could not ask for a better sitter/walker. Never missed a scheduled walk. When we came back our girl was happy and relaxed. Lucas will now be our go-to for when we need a sitter/walker.”
About: Of all animals I have the most experience with dogs. I love dogs all shapes and sizes We've always had a dog at home and I have lots of experience, caring for playing with and walking dogs, including bath time. I'm a recent graduate of heritage high school. I took agriculture at school and worked with the animals on our school farm I'm looking to do rover as often as possible. I don't have any other obligations at this time. So I can dedicate myself to your pets. I am very careful about fences and doors. I'm mindful of owner instructions regarding where their pets can be. And where they are not allowed. I am mindful of them while they are eaten. And while they are playing, to make sure that they remain safe. I checked the pavement before I take a dog out on walks to make sure it's not too hot and always make sure to wash their bowls so that I can help prevent bacteria
“Kim is absolutely AMAZING. She is thorough, thoughtful, caring and knowledgeable. We needed a same day request for our cat and dog and she was able to accommodate. My past experience with Rover was fine. I came back, but I wasn’t expecting much more than hopefully finding someone to water and feed our pets. Kim found time for a meet and greet before we left and made sure everything and everyone was prepped. She built in additional requests to the engagement like an additional stop in on one day. She filled out cards on each visit while we were away and sent pictures with them so we knew how our boys were doing while we were away. This was the first time we got back from being away that our pets didn’t give us the cold shoulder 🤣 They were so well cared for, happy and comfortable it was as if we weren’t even gone. She was just an incredible delight to work with and I plan to book with her anytime I need to be away.”
“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: My love for animals I've had my whole life & cared for my own furr-babies my whole adulthood, Right now I care for my own 2 beautiful furr-babie cats myself & It wasn't until a couple of years ago through my house cleaning service & the relationships I built with my customers & there pets (which I still do) has provided me the experience to care for other pets. I have experience in house/dog sitting, a lil. Dog grooming, & visits to homes to walk, feed & play with, I've dog sat with puppies as well, I have the ability & knowledge to adapt to the animals personalities (because they are all different) but more Importantly I have so much love to give to all animals. I work part-time as a housekeeper during the week days. So my availability is pretty open after 3pm on the week days & my weekends are completely open for any time of the day & I can be available for house/dog sitting as long as I know a few days ahead time I can schedule my job around it no problem. Well Every pet is different with there own personalities & with that being said, It goes without saying first & foremost you have to respect the pet, the owner & there home as well as any care specific required. In other words we have to care for them just like there one of the family members by giving them all your love & attention needed.
About: I know what it’s like to be an anxious mom to a furbaby and wonder if your pet sitter will show up the way you need them to. I have had four dogs since the age of 12 and love them more than anything else! I also had 3 cats when I was younger :) I will do everything in my power to show your babies love and give them top rated care! I currently have open availability and pet sitting is my sole job. I am able to care for senior pets and provide pills as well. :) reach out with any questions! I just moved here from Chicago and right now I’m just babysitting so I haven’t a lot of flexibility and time to care for your baby! I do not offer services at my home at this time but look forward to working with your pets and providing them with the highest level of care and adhering to all routines
About: What sets me apart is the trust I've built with my clients. Many are repeat clients who feel comfortable leaving their pets in my care, even for vacations lasting over a month long. I'm reliable, highly responsive, and believe communication is key. I'll keep you updated with photos and messages while following your pet's routine to help them feel safe, comfortable, and loved. From tiny cats to large dogs, I treat every animal as if they were my own and every home with the utmost respect, so you can enjoy your time away with complete peace of mind. I have a flexible schedule, which allows me to provide pets with plenty of attention, exercise, and companionship throughout the day rather than just quick check-ins. Whether it's walks, playtime, feeding, or simply keeping them company, I enjoy making sure each pet feels comfortable and cared for. As a pet owner myself, I understand the importance of consistency and sticking to your pet's normal routine. I always strive to make them feel safe, happy, and loved while you're away. I believe pets are happiest when they can stick to their normal routine. During overnight stays, I provide full care including feeding, fresh water, walks, potty breaks, playtime, cuddles, and any medications or special instructions if needed.
“Ana was Amazing! I was worried about leaving my cats for a week, especially because one of them is shy around new people, but my cats really seemed to like Ana. I felt very comfortable with the whole process. She even offered to water my plants! I will definitely reach out to her again if we need a sitter.”
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.
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.
“Once again, Monica saved the day! I had a last minute request, and she was so helpful and accommodating. She gives me such peace of mind, and she checks in with me in real-time with photos of my very happy Tango! Having a dog with diabetes makes is very difficult to leave town last minute, and I’m so thankful for Monica and Rover!”
About: Hello, my name is Belinda. I have been a fur mom for 10 years and I truly love spending time with dogs. I’m able to give your dog all the attention needed, and they would never be unattended. Feel free to bring their favourite toys or let them choose from our selection.I have a large gated backyard that your dog will enjoy. All dogs will get plenty outdoor time. My days start early, so drop off and pickup times are pretty flexible. I’m not currently working, so my full time job would be caring for your pet! Flexible schedule and I offer extended stays as well. Only sitting at home I’ve got experience with it all! I’ve also administered medication to dogs of all ages and sizes. lover of all pets, young and old, big and small. ( I DONT ACCEPT PITBULLS). And for allergy reasons I don’t accept CATS We can do walks, hikes, swimming, even to a play day at the park. I Live on the west Side in a house with a fenced yard and friendly neighbours!
The median cost per visit for pet sitting in Winchester is $25
Dog parents share their Rover experiences - Winchester
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!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for pet sitting - Winchester
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winchester average 5 repeat pet sitting clients
FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
The average cost for Pet Sitting in Winchester on Rover is $27.75 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .
As of September 2026, there are 3,539 sitters on Rover offering Pet Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winchester stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Yes, you can find sitters who have experience with handling special pet needs in Winchester. On Rover:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Connect anywhere with the Rover app
