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 85 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%.
“Angela was wonderful and attentive with our two cats. She’s highly communicative and took great care of our cats, and our home, during twice daily drop in visits. We came back to two happy boys. I absolutely recommend Angela!”
“Can I give ten stars?? I am so happy we had James to look after our kitty while we were on a rare family vacation! The daily updates and the many pictures and videos were wonderful and made us know right from the start that we had the right person. I 100% recommend James for any pet-sitting job. Ray is happy we're back, but I can see he misses James now!! Thank you, James - you are awesome!”
“Noila was great at taking care of our 2 cats! Very considerate about a few things that I had left out and asking questions about how to best take care of both them and our house. Very recommended.”
“Bonnie is great with my two cats who have very different personalities. She has gained the trust of our shy cat, which is hard to do! She keeps us updated on them and sends super cute pictures of them.”
“Natalie was so great! She took awesome care of both our cats for several days. Reports and photos were thorough so we could relax on vacation knowing all was well. Thank you!”
“Cheryl gave my Eclipse good love and sent me a thorough update of how it went and adorable pictures. She also knew I was supposed to get home really late and checked in with me that I got home safely!”
“Kerri is extremely flexible and wonderful with our pup. She is patient and kind. Our pup is the happiest to see her! She is definitely our go-to person to entrust our pup’s care !”
About: For the last two and a half years I have been taking care and walking my families dog, and the amount of love and care she needs makes me even more eager to help out whenever needed because dogs and in general pets are a humans real companion. I have also recently took care my family friends two tall and fluffy poodles and it was the best 10 days of my life. I am a full time student, and have another part time job. I am very willing to walk your dog after school. I am also willing to wake up very early (about 6 am) to walk pets right before school starts. My weekends are often free and most times I’ll be available on every second weekend of the month after 5:30 pm. I unfortunately cannot have pets in the apartment I am living in currently. I would be very happy to get familiar with one’s home and see what also the dog’s needs may be and I’m willing to adjust to whatever a pet may need.
“I really cant say enough about how amazing Shawn was! She was so helpful as we were leaving our dog home alone overnight for the first time and also using Rover for the first time. She was super communicative, had so many great suggestions for how to arrange visits, and answered all our questions in detail. She is very professional and you can tell she cares a lot about the dogs she watches. Would book with her again in a heartbeat!”
“Thank you, Jolene, for checking in on my two cats over a holiday weekend with a last minute booking! Jolene’s communication and timing was excellent. While checking on the cats, she filled their bowls, gave them treats, and brushed them. I appreciated her time and attention!”
About: For the past few years now I’ve been a dog sitter for my family and friends, walking, playing, feeding, and cleaning up after them I can house sit, dog walk, and do drop in visits, Any time of the day Mondays to Fridays, And weekends if needed anything works. I get to learn pets usually routine. How many times a day to walk them, when and how to feed them, and their bed time.
“Caroline was available during a busy time of year and super flexible to accommodate a 30-min visit with my cat, Ms. M. We scheduled a quick check-in visit beforehand and she met Ms. M for about 30 minutes, reviewed any instructions, and I left her a set of keys. I appreciated having someone to make sure my cat had a bowl of wet food and some company while I am away for a week. Caroline was also flexible in setting up a time to handoff my spare set of keys. All and all it was a smooth experience and I’d recommend Caroline to others looking for cat care!”
“Lindsey was great with my two pups. Twila is only 6-months-old and she's quite shy, while my other dog Chester is just over two-years-old. I had Lindsey do check ins the first week we got Twila as I was adjusting my work hours to accommodate a new puppy. Lindsey was timely, caring and patient with both of my dogs. I highly recommend her!”
About: I have my own dog who loves company. Your dog will get ample activity with walks, running time in a fenced yard, play time and cuddles. Work from home with a lot of time through the day to spend with pets. At home during weekends so expect longer more fun dog walks. Have a fenced yard and our own dog who loves company. You will need to provide a crate or bedding for their sleep and food. All else will be taken care of.
“We recently moved to a new apt and needed a new sitter for our 10 year old kitty. Carol did a great job with her in all ways. Carol kept her routine and spoiled her the way we do. Our cat was relaxed and well taken care of by Carol. Highly recommend her pet services.”
The median cost per visit for pet sitting in Winchester is $25
Pet parents share their Rover experiences - Winchester
Monica was really great when she came the first day and the key didn’t work! We were able to work together for her to find a way in so we didn’t have to come back early from vacation. She came for exactly 30 min and hung out with our cat and he was taken care of which is all we can ask for.
Matilde is an attentive, friendly, and reliable pet sitter. She sent great detailed updates and photos of our cat, Frankie, while we were away, and even came by early to meet us before our trip. Frankie has some special dietary needs and Matilde made sure she was cared for, while also giving her plenty of cuddles and attention. We highly recommend her for pet sitting needs and can’t wait to have her take care of Frankie again!
It's always a relief to know that Caitlin's looking after Jenny when I can't be there. I know Caitlin not only takes care of food, water, and other necessities. She also spends time with Jenny and let me know how she's doing. I absolutely recommend Caitlin for anyone's pet sitting needs.
This was our first experience with a pet sitter since moving to the United States, so I was a little nervous about leaving our house keys with someone. I was also worried because my English is not very good and I wasn’t sure if I would be able to communicate my wishes clearly. However, she was incredibly kind, caring, and clearly someone who truly loves animals. She made us feel completely comfortable and gave us great peace of mind while we were away. I would absolutely ask her to take care of our precious cats again in the future. Thank you so much for taking such wonderful care of them!
Jillian took great care of my cats while I was out of town. She took extra time to make sure my cat was OK after he ate too quickly and vomited his food, and reached out to offer extra assistance if he needed it. I will definitely rebook with her the next time I need a cat sitter.
Meg was a fantastic with our two older cats who require a little extra in their age, and they both warmed up to her immediately. She easily took on daily meds for one who can be difficult and gave lots of attention overall to both cats. She was very responsive and sent great updates so I didn't worry at all. She even swept up litter and did kitty dishes before she left! Thank you, Meg!
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 6 repeat pet sitting clients
FAQs for Drop-In Visits - Winchester
Frequently asked questions about Rover
The average cost for Pet Sitting in Winchester on Rover is $32.1 per visit (as of August 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 August 2026, there are 10,730 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:
- 90% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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.
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