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%.
“Bonnie was fantastic! She took great care of our cats and hens and sent updates and pictures regularly. When we had an emergency with one of our pets, she really went beyond taking them to the animal hospital late at night. I would recommend her anytime.”
“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!”
“Angela has been very reliable for us taking care of our cat. There was a Blizzard while we were away and she was great about communicating and she made up the visit on a different day. She brought our packages and mail in for us too which was nice of her.”
“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!”
“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!”
“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!”
“Caroline was very friendly. She did a great job taking care of our cat Leo while we were away. Would highly recommend and rebook with her again the next time we go away! Thank you Caroline”
“Caitlin took amazing care of my cat! She is very reliable and responsive in her communications and always makes sure to send plenty of pet pictures. I always come home to a happy cat thanks to Caitlin!”
“Kathryne took excellent care of our 2 dogs and at last-minute notice! She was very responsive to messages and flexible when there was a slight schedule change. Would not hesitate to book again!”
“Elisangela and her girls were amazing! She took great care of our sweet cat Rudy when we were away for a long weekend. She was highly communicative throughout the entire process and left us feeling totally at ease that our guy was in great hands. We would recommend her and rebook with absolutely no hesitation!”
“Page checked in on my cat while I was away for the holidays. Not only did I receive the most heart-warming photos, Page also was kind enough to bring packages inside that had been delivered after I left. Page is very easy to communicate with and is thoughtful as well. Highly recommend!”
“As we just moved to a new place and did not find a cat sitter yet. After reading the positive reviews we decided to reach out to Kimm & Kenn S. Kimm has been such a treasure during our time away. From the get go she communicated very timely, clearly and really wanted to make sure she understood what we were looking for. Throughout our time away she kept us up to date on our cat's wellbeing. We are so happy she took care of our furry friend and will definitely reach out again in the future. Thank you, Kimm!”
“Yesika did an amazing job with my 1-year-old cat, Timmy. She was communicative, thoughtful, and extremely knowledgeable. She followed all of my instructions for visits and sent detailed updates. He had a skin irritation that popped up just before I went away, and she was so helpful in taking care of his skin on top of everything else. I felt so much less stressed being away from him knowing she was there! I will absolutely hire her again.”
“Heather was amazing to work with! She was a huge help walking our dogs while we were away for four weeks. My dogs loved her and she was so kind, taking such good care of both our active 5 year old Frenchie and our senior Frenchie and sending great pictures and updates along the way. She’s the best! ❤️”
“We have been using Shawn for over 6 months for weekday drop-in visits with a very elderly dog. Shawn has been 100% reliable and a total pro the one time that the dog became very ill while home alone in the morning. Shawn invented a new outside game for our 13-yr-old pup, and now the dog wants to play the Shawn game anytime we are in the yard. We feel extremely fortunate to have found Shawn on Rover…she gives us total peace of mind that our wonderful dog is well-cared for. Shawn is completely trustworthy and totally dedicated to the well-being of our pet.”
“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 !”
The median cost per visit for pet sitting in Winchester is $25
Pet parents share their Rover experiences - Winchester
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.
Monica has been so terrific watching Willow while we are at work. Willow was recovering from an Injury and Monica adapted wonderfully to assist her as needed. and Monica’s positive attitude, flexibility, and frequent updates make her one of our favorite pet-sitters ever! Strongly recommend!
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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