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 has a calming presence. My boy is anxious and relaxed with her. She is punctual and gave my boy just what he needed to make the visit successful. Highly recommend Kristen.”
About: I have been dog sitting for over 3 years! I love spending time with dogs! I have been slowing practicing grooming dog because I plan on starting my own dog grooming/sitting business! I am currently working a part-time job so I have extra time and would love to play/let your dog out or feed them! If possible I would like to come meet the dog(s) a few days before I house sit for you so I can see how you do everything!
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've been a pet groomer for 17 years, with 10 years under ownership of a veterinarian clinic. I've been doing pet sitting in client's homes for several years. I love all animals, but have a special love for the elderly and ailing. I'm experienced in giving medications, injections, grooming, etc. I work 8-4 Tuesday through Friday, and 8-2 on Saturdays. I do sitting overnight, mornings before work, and afternoon/evenings after work. In some cases, if I am overnight sitting, I may also be able to bring a dog to work for daycare as well. Requirements for that include proof of rabies vaccination, spay/neuter after 6 months, and an understanding of general temperament. I have several years experience dog sitting in client's homes. I'm able to walk, play, administrator medications, feed, and do daily maintenance for coat and skin.
About: I provide a large area to play and toys and activities to engage in for wonderful fun. I have plenty of places like trails to walk them.I groom everyday to keep maintenance and beauty. I give out lots of love and attention to make each feel special. I have had dogs for about 24 years and have provided care for some over the years. I know how to handle emergency situations when it comes to dogs. I have groomed many bigger dogs like great pyrenees and as small as yorkies. I have 1 dog of my own that is healthy and happy and are willing to make this love for my dogs as well as others, a full time job. I look forward to providing helpful services to you and your dog. I'm currently working part-time, so I'll have plenty of time to play with your pups and give them lots of attention to make them feel right at home I have a fenced in play area and a large farm for them to enjoy on leashed walks. I can easily crate your dog if needed if they need a safe place to adjust to the new environment.
“Gabby did awesome, we've used her for years, glad to see shes stretching her arms and joining rover! Our dogs love her to death and she is great with them. All 3 are pitbulls and she has no issues Keeping them spoiled and happy! Would book her anytime ! A very responsible and respectful young woman .”
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.
“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.”
“Second time went as smoothly as the first and cats were happy, also always willing to go the extra mile offering to water my plants which I really appreciate! I will definitely be a returning/recurring client, thank you!”
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
About: I’ve always been around dogs my whole life. No matter what I’ve always put my pets first. They are truly my babies. And I’ll treat your fur baby like it’s my own. I can do weekly walks. Pet sitting. Im a really big animal person. And ill try my hardest to work around your busy schedule also!! My own puppies are always outside enjoying the nice weather. But they truly are cuddle bugs.im a huge outside person so many many walks to be enjoyed!!
About: I’ve grown up with dogs, cats, horses, you name it. Animals are underrated as members of the family in my opinion and I just want to make sure any animal in my care is treated like family. I take care of my animals (two dogs and a kitty cat) daily and they have a pretty set routine, I would be working my schedule around their routine and working on my days off. I’m happy to drop in and check on your babies and give them love and attention on long work days. I know how stressful it is to be at work knowing your baby is alone at home and I’m happy to help!
“Kayla was great. I scheduled her to do some drop in visits while I traveled to watch my cats. She showed up on time and took care of everything I requested. I highly recommend her if you need someone to take care of your pets while you are away.”
Over 18 pet parents in Winchester have booked pet sitting
Winchester pet parents share their Rover experiences
Della does such a great job with our little Ziggy. I would trust her implicitly to take care if any animals. She is professional. Communicates well and keeps us updated. I would trust her to stay in our home to do overnights or walks with our fur babies. Thank you Della for such great service.
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.
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 Mar 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 Mar 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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