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.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester pet sitters
“Lena was happy to see us and not desperate and angry. A tribute to Erin giving her not just the care she needs, but the companionship too while we're gone. We're so grateful for that. Erin goes above and beyond, making sure to take care of the trash and recycling, and leaving the house clean. We're so grateful for her care.”
“Shawn dropped in to take care of our two cats multiple days during our long vacation. It was a huge relief knowing they were in good hands and getting photos each day. She followed our detailed feeding instructions that involved wet food with medication mixed in, and measuring out dry food on a scale. She also gave us detailed updates on their behavior and it was clear she really cared about their comfort and mood while we were gone. Thank you Shawn, would definitely book again!”
“Natalie took excellent care of my cat. She was responsive and reliable, giving me peace of mind while away. I’ll be booking with her again in the future!”
“Alina was great with my dog, Moose! She was prompt and made sure to take up the whole 30 minutes, and my dog really enjoyed her company! I would recommend Alina to anyone looking for a dog walker in the area.”
About: I grew up caring for dogs of various sizes and breeds. My children and I cherish the love and joy of having a pet to care for and play with. I no longer own a dog of my own, however we still want a furry friend to share our lives with. I'm an elementary teacher by day, however have afternoons, evenings, weekends, school vacations, and summers available to care for your dog. I am not home during most school days, however will not host a dog unless I am also scheduled to be home. There is a lot of space for one or two dogs to play inside our home. When caring for dogs, I will take them for walks in the park across the street or through one of the many walking paths in this area. It's our pleasure to play with your dog; keeping them engaged makes for a fun experience and helps keep their minds off of missing you!
“Elisa was responsive and sent detailed photos with each visit. She also responded well despite my cat having bitten her (a previously unseen behavior) and completed the visits.”
“I asked Liz to drop in on my kiddos for a 2nd time. They really enjoy her visits. And, it provides such peace of mind for me knowing they have a familiar face stopping by to care for them and play with them. Thanks again, Liz!!”
“Bonnie is wonderful! Very accomodating and great at following up. Because I am not computer and internet savvy, I made some mistakes with registering. On her own time, Bonnie worked diligently on her own time to correct my mistake and I got a refund from Rover.com. I know she has a lot of clients but it always feels as if you are her only client. I can't recommend her highly enough!”
“Zijia took amazing care of my cat while I was away. My cat is usually shy around new people, but he warmed up quickly thanks to his gentle and patient approach. I came home to a happy, relaxed cat and a clean space. I would absolutely recommend Zijia to anyone looking for a kind and reliable pet sitter.”
“Julia was fantastic- we really loved her watching our two cats! It was important to us that they have play time and attention while we were away, and they clearly loved her.”
About: I grew up with cats and have always found joy in making sure they’re well loved and cared for at every stage of life. Even after moving away from home, I shared pets with roommates and had the opportunity to love and care for them, just like my own. Now, I’m mom to two tuxedo cats who are smart, rambunctious, and cuddly all at once—and a tween-age beagle mix who’s sassy, full of energy, and a total snuggle bug. Though I’m newer to dog ownership myself, friends and family have consistently trusted me to care for their dogs. With my own dog, I’ve learned how important it is to read and respect each pet’s unique cues, and I’m happy to learn from you about how to best support your pup and to align with your goals. I’m a career special education teacher and high school program director/administrator, which means I’m detail-oriented, responsive, conscientious, and cautious—qualities I bring to every pet I care for, treating them just as I would my own. I have a flexible summer schedule. While my schedule for the fall is not yet solidified, I am consistently available for early morning or late afternoon drop ins. I am very detail oriented, and will ensure that I have the utmost clarity on your pets’ care instructions. I am extremely careful when ensuring that I am following all safety requests (I.e. arming security systems, locking/ closing egresses), and will happily meet your individual requests.
“Shannon is amazing! So responsible and attentive with my dogs. Really pays attention to detail and gives very detailed report cards. Great sitter!”
“Needed a sitter while I went away for a week. Cathalina was great with my kitty Domino, who is moody and under the impression he’s a dog. She played with him even after he tried to get her at the start of one of their visits! Hero in my book lol great communication and lots of pics! Definitely will book her again for my next trip!”
“Jordan came to the rescue when our last cat sitter unexpectedly backed out. He's been very accommodating and went to check on our cat same night. He also sent us tons of photos so we know our cat is well taken care of”
“Sara was very accommodating with a last minute request and took great care of Luna! She provided thorough updates and pictures as well. Will definitely book with her again!”
“Blane was super organized— reached out in advance to come meet the kitties and see the house. The updates we got were so full of love and we 100% knew the cats were in good hands. It was also very easy to ask for a few extra things like making sure the AC was on and the windows were closed when the weather changed. Thanks so much!! We’ll definitely be repeat customers.”
About: Hi guys! My name is Maude, I am a 27 year old small business owner living in Stoneham with my best friend Stella, a 5 year old golden retriever. I’ve always had a passion for animals and have owned dogs for over 15 years, raising them from puppyhood. I know how important your dog is to you and my #1 goal is to return them to you SAFE and HAPPY, along with your peace of mind. We can’t wait to meet you 😊 I know firsthand how stressful it can be to leave your pup with a sitter/walker - my top priority is ensuring that you feel confident in the quality of your dog’s care under my watch and to give your pet my full 1:1 care and attention like I do with my own dog. As a small business owner, I’m able to make my own schedule and can be flexible with fitting your pet’s care into my daily routine. Safety is my number one priority. I know how hard it is to leave your fur baby in someone else’s hands, so my goal is to give you some peace of mind with frequent updates and attentive care.
About: I don’t just care for pets, I truly listen to them, bringing calm and steady energy and cater to each animal to make them feel safe and understood. No matter how busy my day gets, I always make sure there’s dedicated time for the pets I care for. Whether it’s a walk, playtime, or just some quiet attention, they’re a priority and I’m fully present with them. When I’m caring for pets in their own home, I make sure to keep their routine as normal as possible. I give them plenty of attention, stick to their feeding and exercise schedule, and create a calm, safe environment where they feel comfortable. I treat their home, and them, with respect, just like they’re my own.
“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: Not only have I cared for my own dogs and my friends' dogs, but I volunteer at Zoo New England as an animal Keeper's aid! I've been with Stone Zoo for 2 years now, and transitioned to animal care about a year and a half ago because the education staff knows that I own snakes and have a passion for all animals. I would love to meet your furry, scaly or slimy friends and help you out with their care! I am a freelance opera singer, so my schedule is very flexible. If I'm working on a show in town, I usually have a lot of daytime availability. I do travel for work sometimes, but I always know my schedule well in advance. I have taken dogs for walks, play-dates, given food, medicine, and stayed over night with dogs in their person's house for over a week at a time.
Loving pet sitters in your neighborhood
Search Results
Erin F.Star Sitter
“Lena was happy to see us and not desperate and angry. A tribute to Erin giving her not just the care she needs, but the companionship too while we're gone. We're so grateful for that. Erin goes above and beyond, making sure to take care of the trash and recycling, and leaving the house clean. We're so grateful for her care.”
Shawn V.Star Sitter
“Shawn dropped in to take care of our two cats multiple days during our long vacation. It was a huge relief knowing they were in good hands and getting photos each day. She followed our detailed feeding instructions that involved wet food with medication mixed in, and measuring out dry food on a scale. She also gave us detailed updates on their behavior and it was clear she really cared about their comfort and mood while we were gone. Thank you Shawn, would definitely book again!”
Natalie J.Star Sitter
“Natalie took excellent care of my cat. She was responsive and reliable, giving me peace of mind while away. I’ll be booking with her again in the future!”
Alina M.Star Sitter
“Alina was great with my dog, Moose! She was prompt and made sure to take up the whole 30 minutes, and my dog really enjoyed her company! I would recommend Alina to anyone looking for a dog walker in the area.”
Michael D.Star Sitter
About: I grew up caring for dogs of various sizes and breeds. My children and I cherish the love and joy of having a pet to care for and play with. I no longer own a dog of my own, however we still want a furry friend to share our lives with. I'm an elementary teacher by day, however have afternoons, evenings, weekends, school vacations, and summers available to care for your dog. I am not home during most school days, however will not host a dog unless I am also scheduled to be home. There is a lot of space for one or two dogs to play inside our home. When caring for dogs, I will take them for walks in the park across the street or through one of the many walking paths in this area. It's our pleasure to play with your dog; keeping them engaged makes for a fun experience and helps keep their minds off of missing you!
Elisangela L.Star Sitter
“Elisa was responsive and sent detailed photos with each visit. She also responded well despite my cat having bitten her (a previously unseen behavior) and completed the visits.”
Liz M.Star Sitter
“I asked Liz to drop in on my kiddos for a 2nd time. They really enjoy her visits. And, it provides such peace of mind for me knowing they have a familiar face stopping by to care for them and play with them. Thanks again, Liz!!”
Bonnie K.
Star Sitter
“Bonnie is wonderful! Very accomodating and great at following up. Because I am not computer and internet savvy, I made some mistakes with registering. On her own time, Bonnie worked diligently on her own time to correct my mistake and I got a refund from Rover.com. I know she has a lot of clients but it always feels as if you are her only client. I can't recommend her highly enough!”
Zijia C.
“Zijia took amazing care of my cat while I was away. My cat is usually shy around new people, but he warmed up quickly thanks to his gentle and patient approach. I came home to a happy, relaxed cat and a clean space. I would absolutely recommend Zijia to anyone looking for a kind and reliable pet sitter.”
Julia B.Star Sitter
“Julia was fantastic- we really loved her watching our two cats! It was important to us that they have play time and attention while we were away, and they clearly loved her.”
Angela R.
“Angela is genuine, loving, caring, and responsible. She has been a pet owner to two cats for several years and raised them since young kittens, and has also adopted and been raising a puppy for over a year now. She is intuitive to her animals’ needs and body language, and her patience is unmatched! Angela’s love for animals runs deep and she has always treated my pets like her own. I can always trust that my pets will be well-loved and cared for in Angela’s hands!”
Shannon S.Star Sitter
“Shannon is amazing! So responsible and attentive with my dogs. Really pays attention to detail and gives very detailed report cards. Great sitter!”
Cathalina M.Star Sitter
“Needed a sitter while I went away for a week. Cathalina was great with my kitty Domino, who is moody and under the impression he’s a dog. She played with him even after he tried to get her at the start of one of their visits! Hero in my book lol great communication and lots of pics! Definitely will book her again for my next trip!”
Jordan D.
“Jordan came to the rescue when our last cat sitter unexpectedly backed out. He's been very accommodating and went to check on our cat same night. He also sent us tons of photos so we know our cat is well taken care of”
Sara & Ari B.Star Sitter
“Sara was very accommodating with a last minute request and took great care of Luna! She provided thorough updates and pictures as well. Will definitely book with her again!”
Blane H.Star Sitter
“Blane was super organized— reached out in advance to come meet the kitties and see the house. The updates we got were so full of love and we 100% knew the cats were in good hands. It was also very easy to ask for a few extra things like making sure the AC was on and the windows were closed when the weather changed. Thanks so much!! We’ll definitely be repeat customers.”
Maude G.
“Maude is the owner of a beautiful two year old English Cream golden retriever and has gained a lot of experience caring for her puppy by doing so first hand! She is responsible, reliable and I would highly recommend her caregiving services to any and all pet owners!”
Michelle T.
“I’ve watched her grow up with a real love for animals and a natural sense of empathy. She’s always been gentle, patient, and caring, even as a kid. I think animals can pick up on that kind of energy because I can’t recall a single bad experience that she’s had with them. She genuinely cares about their well being and treats them with respect, which makes her a great pet caretaker.”
Jolene G.
“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!”
Margaret F.
“Margaret has taken incredible care of my dog since he was a year old (and he just turned 13)! She has walked him, fed him, helped him when he needed medical care, and most importantly, she loves him--and the feeling is extremely mutual. She is absolutely one of his top 3 people on the planet. She's conscientious, responsive, and thoughtful, and has a genuine love for animals that they can sense. There's no one I feel more comfortable leaving him with. Cannot recommend her highly enough!”
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!
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.
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 Jul 2025 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 Jul 2025, there are 1,963 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, 84% of Winchester pet sitters respond in under an hour.
Pet sitters in Winchester have an average of 11 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 1,963 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 96% of pet sitters offer daily exercise, 91% offer medication administration, and 86% 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.
Connect anywhere with the Rover app
