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.
“Kristen was willing to take on our very, VERY anxious dog without hesitation. Considering how challenging Otis can be, I know "average" pets would do wonderfully with Kristen and she truly loves taking care of pets.”
About: Our home has always been filled with dogs and cats. The strays find me and know they will always have a spacial place to call their own. I own a small consulting business and have flexibility with my schedule. I am easing into early retirement and looking to share my love of animals. I am an experienced professional who is phasing into early retirement. I have spent years traveling and have an empathy for pet parents who have to leave their fur babies while away from home.
About: I have three years experience with walking and boarding dogs at a dog boarding facility. I can also give medicine and insulin shots as needed. It’s always been my dream to work with dogs/cats full time. So, my schedule is normally open! I also accept clients on most weekends as well. My number one goal is to ensure your fur baby is happy and comfortable. I will take time to get to know your dog/cat and become a welcomed face. I’m always ready for play time and giving pets :)
About: I am friends and families go to dog sitter for when there is vacations, or someone is busy. I have been doing this for family and friends for a couple of years now im currently college student and would love to watch over your fur babies! with me being in school and work i’m normally pretty flexible with my schedule as all my classes are early in the morning! I have a huge fence around my yard and two adorable fur babies if yours are needing some company. I will be able to watch over your dog at all times if needed.
“Jenna was amazing with our dog for drop in visits while we were out of town. She was very responsive, timely and took lots of pictures for us. She took the time to hang out with our dog and make sure he was comfortable. We really appreciated everything she did for us as it made this very easy. I'm so happy we found her and look forward to working with her again!”
About: I’ve taken care of & had animals since I was about 10, and would love to help whoever needs assistance. Whether that be puppies or seniors, I am here to help. I can work any day Monday through Friday, and some weekends depending on the schedule. Mornings and afternoons are preferred, but am willing to accommodate to certain needs. We do not own any current pets at the moment, but have a fenced in yard with room to run around. I can accommodate to certain needs.
About: My name is Luke, I am a CATCH Canine Trainer Academy certified dog trainer. I use positive reinforcement to encourage and maintain behaviors. I have always had a passion for working with dogs but after losing one of my rescues to cancer only 2 months after saving her my passion grew. This had inspired me to help owners and their dogs learn and grow together. I am a Co owner of a food truck which we are only operating part time. On the opposite days I have open availability to help support you and your current fur baby. I am unable to offer boarding for animals at this time. I am certified in pet cpr and first aid through ProPetHero by Pro Trainings
“If I could give 10 stars, I would! Christina takes exceptional care of our fur babes and goes above and beyond to help them feel comfortable and happy!!! Christina, you are simply the best!!”
“Shelby was great! She took most excellent care of Sophia and the Dew while we were out of town. She really cares, and we enjoyed getting the pics from her care visits, we would def use her talents again.”
About: I have always had pets as long as I can remember even from being a baby. I love dogs and cats so much and my heart for animals is so big. I have raised so many throughout the years and my adopted dad also owns a veterinarian clinic so I have learned a lot from that as well. I have pretty much open availability. My schedule is 90% flexible 90% of the time. Monday through Sunday. All hours of the day/night. So yeah. I care for my clients pets as they need me to. Whether it be in the fence or on a leash, in the public or in the private. I go directly based on the instructions I get left from the peoples pets I am sitting. Every pet is different.
Over 19 pet parents in Winchester have booked pet sitting
Winchester pet parents share their Rover experiences
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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
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The median cost per night for pet sitting in Winchester is $25
Why Choose Rover?
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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 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 13 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, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available 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 13 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened 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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