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%.
“This is out second booking with Cheryl, this time for a full week of visits, and she was excellent! She treats my pets like her own and genuinely cares for them. We received plenty of pictures and detailed updates after each visit. My family and I definitely could sleep easier being away from our pets knowing they were in her great care!”

“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!”

“James is the best!!! Very communicative, provides full run through of activities and behaviors during the visit. He is very loving to the dogs and takes lots of photos and videos! Will 100% book again.”

“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.”

“Angela has watched my cat Mason twice while I've been out of the country and she put my mind at ease! She sends lovely pictures and updates about him and when I get home, he's very calm and relaxed, rather than stressed from my being away. I'd recommend Angela to any cat parents!”

“Caroline did a great job checking in on my cat while I was away on vacation. She kept everything neat and tidy, paid attention to detail, and was fast/prompt with any communication. Would definitely recommend and will rebook if needed in the future.”

“Charlotte was amazing! She took such great care of our kitties while we were away. We loved her photos and daily updates. She was super easy to communicate with and our nervous cat loved her! I highly recommend Charlotte and will definitely hire her again!”

“Jessica is reliable and responsive, and takes great care of my kitty. I will continue to ask her to take care of Rocco every time I go out of town. Thank you Jessica!”

“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!”

“Sanela is a very responsive cat sitter and goes above and beyond. Our cat seemed ok at initial meeting but for the second visit our cat Beans was mean toward Sanela. It’s unfortunate but cats are cats, Sanela still stayed and gave her treats and shared photos.”

“As always, Yesika is my go to person whenever i’m traveling. Very reliable. I love working with Yesika! Also she sent me cute photos of my cat and i often made them as a wall paper on my phone 🥰”

About: What sets me apart from other sitters is my deep compassion, patience, and experience with dogs who need extra attention—especially those with anxiety or special routines. I have hands-on experience caring for senior dogs, puppies, and pets who struggle with separation anxiety. My own dog, Sasha, has anxiety, so I understand the importance of gentle care, consistency, and emotional support. I treat every pet like family, and I’m committed to creating a calm, safe, and loving environment while you’re away. Whether your pup needs long walks, slow introductions, or just a cozy lap to nap on—I’ve got you covered! Pet care fits naturally into my weekly routine. I have Mondays and Tuesdays off, which gives me plenty of time for daytime walks and drop-ins. On other days, I’m able to fit in visits between school and work—and I don’t mind doing late-night drop-ins if your pet needs evening attention. Caring for animals is something I truly enjoy, so I’m happy to make it a priority in my schedule. I’m dependable, flexible, and always focused on making pets feel safe and loved while you’re away. I only offer pet care in the client’s home because I believe pets are happiest and most comfortable in their own familiar environment. I follow your pet’s routine closely—whether that’s feeding, walks, playtime, or administering medication. I respect your space, keep things tidy, and make sure your pet feels safe, loved, and cared for while you’re away. My goal is always to provide reliable, stress-free care that gives both you and your pet peace of mind.
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.

About: Hi! 😊 I have always loved being around animals, and I have spent most of my life around them. I also look after my family and friends pets when they travel. I am flexible on timing and would love to check in on your cats or pups while you are away any time visit is needed. 🥰 Pets need usual routine and I’d provide everything they need to feel safe and loved, including walks, playtime and rest to reduce stress. I love taking photos of our fun moments, and would gladly share with you! ♥️
Over 30 pet parents in Winchester have booked pet sitting
Winchester pet parents share their Rover experiences
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.
Sanela was amazing! We have a super high energy young cat that needs a lot of play and she did an excellent job in playing with him until he was out of energy. She also did a great job with our older kitty who is all about his special morning soup! We are so happy we picked her and despite the older one not liking many people, he loved being around her immediately. And, even would pose for their daily photo shoot with her, they love her! She is a cat whisperer and we would 110% book again. She also has very reasonable prices for services which is great for our longer trips. And, very respectful of our house rules which is appreciated. Thank you, Sanela! The kitties thank you, too!

My cats, Taz and Luca, loved Allie. This was our first time using Rover, and I wasn't sure how Luca would react — but he surprised us. He was comfortable and even enjoyed playtime. Allie is responsive and easy to communicate with, and I knew my cats were in good hands. Highly recommend!

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 6 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 10,555 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 in Winchester have an average of 14 years of experience. Pet sitters with repeat customers have an average of 6 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 10,555 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 95% of pet sitters offer daily exercise, 95% offer medication administration, and 90% 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.






















