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. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Susan was wonderful with my cats, and I would highly recommend her to anyone looking for a caring and attentive pet sitter. From the start, you could tell she genuinely cares deeply about animals. She asked thoughtful questions, paid close attention to detail, and ensured my cats received the best possible care. She was also very personable and kept me updated while I was away, which gave me a lot of peace of mind. I've already rebooked her to pet-sit for me again! She’s the best.”

“We’ve had Amber drop in on a few separate occasions now and have had a great experience each time. She’s been attentive to both dogs behaviors and makes sure to check in with questions or concerns. I have a peace of mind when Amber visits if I’ll be away from home for an extended time during the day. Based on the photos, the dogs definitely have a great time with her too!”
“Haley once again did an amazing job taking care of our two cats while we were gone for over a week. They were immediately comfortable with her on the first visit. She sends thorough updates and photos every visit showing them playing and interacting with her. I highly recommend her services. She's very reliable and communicative, and is a great fit even for skittish kitties. It was such a relief to know that she was checking in on our cats while we were gone!”

“Maggie is a natural with animals. She’s calm and confident around them and people too. Our Merry can be shy but she was fine with Maggie right away. Maggie is polite, presents herself well, and always on time, with a good attitude! We will use her again.”


“Can I give Amadie 10 stars??? We had recently lost one of our kitties and had a 10 day vacation scheduled plus we had moved so needed a pet sitter for our senior, very shy kitty. Amadie was the perfect fit! Our senior kitty warmed up to her and she actually let Amadie pet her a few times. This was a first for anyone besides me or my husband! The patience, love and care she showed to Luna was beyond anything we ever expected. She also was so caring for our home and reached out with questions. Amadie communicated with us daily, pictures and updates. We will definitely ask Amadie to care for Luna again.”

“I would recommend Elizabeth for all your dog watching and walking needs. She was very professional and my dogs were friendly with her. She has a lot of experience with dogs. Cheers, Kevin G”

“Ayden was a fantastic house sitter. He took incredible care of our numerous animals, and even noticed that our pellet stove had malfunctioned and let us know! We highly recommend him.”

About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.
“Kiersten was very prompt. Spent the agreed amount of time with our dog. Everything was done according to directions. Our dog, who can be skittish with some people, enjoyed her visit.”

“Nadine did an amazing job with our cat. Lots of playtime and pets when she stopped by for an evening drop-in. She kindly sent videos and pictures too! We hope to use Nadine again in the future!”

“Kendra took excellent care of our two kitties while we were away! I was amazed by the level of thoroughness checking on each one and how they warmed up to her. Cats were very well taken care of and the pet areas clean when we returned home. The daily updates with pictures of our kitties was a huge comfort... Looking forward to having Kendra watch our kitties again in the future!”

About: I have taken care of cats, dogs, Small animals like mice, guinea pigs, fish, turtles. All way to farm animals like sheep, goats and even horses. Due to growing up in small town farming community. Currently I am supervising and helping my teenage daughter care for multiple miniature and full size horses in Leverett MA. I also have two wonderfully spoiled cats and a dog at home. Have some openings in evening and most weekends as at this time I do have a full time 9-5 job. Looking to see where this goes. I do not have fenced in yard but I keep my current dog on tie out or 50ft lead. Very quiet not normally traveled area around house with big yard to play. At clients home depends on environment there. Would prefer no off leash unless securely fenced area.
About: I used to babysit for my friends, family membersand & neighbors. As well as I've had many pets of my own; cats, dogs guinea pigs, hamsters, you name it. I'm very good at handling bigger dogs. I'm very flexible when it comes to time and will work around your schedule. I'm currently home from college for spring break and my time is very open for both weekends and weekdays. My working hours start at 7am and go till 11pm. (But I can fluctuate with your schedule) I have a fenced backyard. And one very friendly small/medium dog, he's a little shy, but he gets along with everyone. I believe that our pet should be treated like family members. Walks, treats, attention and lots of love.
“Carol took Nora while we went to the botanical garden. She played with her and kept her safe so we could enjoy our time in the gardens. I wish we could take her with us every time we travel ?”

“Elias took fantastic care of my tricky kitty, including administering meds in food and dealing with frozen wet food (Smalls) which is trickier than scooping dry food or opening a can. They were very responsive communication-wise and enthusiastic. I will definitely turn to them again for kitty care when I next leave town.”


About: Hi! I'm Nicole. I'm a software developer & animal lover. I've been around dogs since I was little and have always wanted to adopt one. Caring for dogs with busy owners is a great compromise! Dog owners will love that I will treat their furry pal as if they were mine. They will also love that I have private outdoor space for playtime, anytime, and am right next to central park so there's alot of ground for your furry friend to explore! I truely care about your pets well being so I am consistent with feeding time and will always make sure your furry friend is comfortable, whether its brushing her or refilling her water bowl. I am available Wednesdays and the Weekends for pet sitting, walking, and house sitting. If you are going away for a weekend and need someone to house & pet sit, I'm your girl!
“Emily was amazing with Pepper, my shy hound. Emily showed up promptly for each visit and was very thorough. Even her pre-visit questions were thorough. She is very caring and kept me very informed. I highly recommend Emily.”

Over 1 pet parents in Winchester have booked pet sitting
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The median cost per night for pet sitting in Winchester is $25
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It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
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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 493 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 15 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 493 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, 97% offer medication administration, and 87% 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.



