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
“Erin couldn’t have made our first experience with Rover better! She is super thorough and thoughtful with her visit notes which gave us so much peace of mind and she was always on time, if not early! It was so awesome to see how much our nervous pup took a liking to her. We will definitely be reaching out to her for our future dog-sitting needs!”
“Angela was great with our cat Onyx! She was very nice to chat with during our meet at greet assuring me he would be well cared for during her check ins! We were very happy with the pictures and communication while we were away and will for sure be using her again in the future!”
“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!”
“It was our first time using River and we were so happy when we found Bonnie! Everything went great and our cats seemed calm and cared for when we got home! And thank you for the fun pics and videos! Thank you Bonnie!”
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!
“Ellie was so amazing!! This was my first time using Rover and she did not disappoint! I felt more relaxed being away from my cat and I was very comfortable with her being in my home. I will definitely use her again for future pet sitting needs. Thank you Ellie!!”
“Sabine was great. She took care of my big girl Maine Coon Suka. She was professional and you could tell she loves animals and that she new how to interact with cats. Suka came up to her and let her pet her on the meet and greet. I would hire Sabine 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.”
“10/10 would highly recommend booking with Natalie! This was my first time using a sitter for my cat and Natalie made me feel so much more at ease with the care she provided. She was super communicative, sent lots of pictures, and was flexible with my schedule. I'll definitely be booking again with her in the future!”
“Zika did a great job watching my cat! He provided me with a timely update as well as a variety of cute pics. I was very happy with the communication. I’ll definitely reach out again.”
“Hillary was a great find in the "eleventh hour" of my search for service. She dropped in and took really good care of my dog while I was far away for the day. I felt confident from our first texts and Hillary's generous effort to come to my home for a meet n greet. Hillary followed through with great communication, lots of photos and follow up texts. I would call her again in a heartbeat and highly recommend her services ! Thank you so much!”
“Cathalina provided excellent care for my cat! She was responsive, friendly, and easy to communicate with throughout the process. I would definitely work with her again.”
“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: I’m a dog person! I love meeting new dogs and spending time with them. I’ve taken care of dogs off and on for 20 years (not including my own). I currently have a rat terrier mix - Roxie - who LOVES dog friends and is very playful. I’m a big walker and have experience with dogs on trails as well as in neighborhoods. I’d take care of your dog like my own. Most of my experience is for extended stay house-sitting for families with multiple dogs. I’m not able to have cats in my apartment, but love meeting cats in their own space and would be sure they were well loved and taken care of in your absence. I work from home full-time and have a very flexible schedule which allows me to be available most times of the day. I can work around complicated calendars! I have a fenced yard and a VERY friendly rat-terrier mix named Roxie. For house sitting, Roxie can come with me or stay behind, but she’s great with dogs off all sizes and I’m very careful when bringing her into another dog’s space.
About: I have grown up with dogs my entire life! My best memories are bringing them to lakes growing up and playing in the water with them! I’m currently working full-time but I want to help take care of your pets on the side! After 6pm on weekdays work, along with any time on the weekend with a notice! Smoke-free apartment unit and a lot of walking trails around! I can accommodate to anyone’s living environment! I love going to parks with my dog.
“Caitlin was wonderful with my cat Willow who doesn't take to everyone. They really bonded and I feel that Caitlin went above and beyond in caring for Willow. Highly recommend!”
“Maria and her partner happily accepted a quick meet up before meeting Mochi and I. They were eager, friendly, and very respectful. They spent and hour each day playing, petting, chasing, and cuddling with Mochi. My little Mochi was ecstatic to see them and play with them. Knowing that she was in great, eager, and safe company and while providing her nonstop attention for the hour was the best I could ask for. Would love to have Maria and her partner hang with Mochi again soon!”
Loving pet sitters in your neighborhood
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Erin F.Star Sitter
“Erin couldn’t have made our first experience with Rover better! She is super thorough and thoughtful with her visit notes which gave us so much peace of mind and she was always on time, if not early! It was so awesome to see how much our nervous pup took a liking to her. We will definitely be reaching out to her for our future dog-sitting needs!”
Angela R.Star Sitter
“Angela was great with our cat Onyx! She was very nice to chat with during our meet at greet assuring me he would be well cared for during her check ins! We were very happy with the pictures and communication while we were away and will for sure be using her again in the future!”
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!”
Bonnie K.
Star Sitter
“It was our first time using River and we were so happy when we found Bonnie! Everything went great and our cats seemed calm and cared for when we got home! And thank you for the fun pics and videos! Thank you Bonnie!”
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
“Ellie was so amazing!! This was my first time using Rover and she did not disappoint! I felt more relaxed being away from my cat and I was very comfortable with her being in my home. I will definitely use her again for future pet sitting needs. Thank you Ellie!!”
Sabine G.
“Sabine was great. She took care of my big girl Maine Coon Suka. She was professional and you could tell she loves animals and that she new how to interact with cats. Suka came up to her and let her pet her on the meet and greet. I would hire Sabine 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.”
Natalie J.Star Sitter
“10/10 would highly recommend booking with Natalie! This was my first time using a sitter for my cat and Natalie made me feel so much more at ease with the care she provided. She was super communicative, sent lots of pictures, and was flexible with my schedule. I'll definitely be booking again with her in the future!”
Kelly O.
“Kelly was great! Quick responses and was wonderful to work with. I definitely recommend her services!”
Zijia C.Star Sitter
“Zika did a great job watching my cat! He provided me with a timely update as well as a variety of cute pics. I was very happy with the communication. I’ll definitely reach out again.”
Hillary C.Star Sitter
“Hillary was a great find in the "eleventh hour" of my search for service. She dropped in and took really good care of my dog while I was far away for the day. I felt confident from our first texts and Hillary's generous effort to come to my home for a meet n greet. Hillary followed through with great communication, lots of photos and follow up texts. I would call her again in a heartbeat and highly recommend her services ! Thank you so much!”
Emilie d.
“Emilie took great care of my cat Josie. She was responsive and updated me with lots of cute and silly pictures to ensure me she was ok while I was gone!”
Cathalina M.Star Sitter
“Cathalina provided excellent care for my cat! She was responsive, friendly, and easy to communicate with throughout the process. I would definitely work with her again.”
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!”
Annmarie M.
“Annmarie has taken wonderful care of our two golden retrievers (now 1 and 4 years old) on several occasions over the last year! She is dependable, compassionate and very knowledgeable on all things dog related. Our pups love her and her dog and always look forward to seeing them. I recommend Annmarie for all of your dog needs without hesitation!”
Alicia B.
“Alicia was absolutely amazing with our Shih Tzu, Chloe. She was kind, caring, and nurturing, giving Chloe plenty of love, attention, cuddles, and playtime. Chloe had the best weekend ever with Alicia dog-sitting. We felt completely at ease knowing she was in such great hands, and it’s clear Alicia truly loves and cares for the pets she watches. Highly recommend her to anyone looking for a trustworthy and loving pet caregiver!”
Caitlin M.Star Sitter
“Caitlin was wonderful with my cat Willow who doesn't take to everyone. They really bonded and I feel that Caitlin went above and beyond in caring for Willow. Highly recommend!”
Jessica M.
“Jessica is great. Patient, kind and communicative.”
Maria J.
“Maria and her partner happily accepted a quick meet up before meeting Mochi and I. They were eager, friendly, and very respectful. They spent and hour each day playing, petting, chasing, and cuddling with Mochi. My little Mochi was ecstatic to see them and play with them. Knowing that she was in great, eager, and safe company and while providing her nonstop attention for the hour was the best I could ask for. Would love to have Maria and her partner hang with Mochi again soon!”
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 Aug 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 Aug 2025, there are 2,000 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 12 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 2,000 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.
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