House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.

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Top rated Winchester house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: You have my word I will take good care of your animals while away and will treat them as my own, I have worked 31 years in the medical field and have raises guinea pigs, rabbits, fish, dogs, cats, birds, so have a lot of experience with animals. I live alone and flexible, work from home full time, can check on pets before work- lunch hour and after work during week and available weekends I will need to come to your home to take care of animals in their home environment- I can check on them morning , lunch hour or after work and weekends are open - feed water walks clean up after etc I am looking forward to spoiling your pet babies!!!
“My dogs were friendly and playful with Ryan immediately upon meeting, which I take to be a good sign. Ryan was friendly, transparent and communicated well. I’ll happily be a returning customer.”

“An excellent house and pet sitter. We can count on Christian to take care of our pets and house. He communicated well and assisted with deliveries and house services. We hope he can come back again and he get our highest recommendation.”

“Addie was exceptional in every way. She asked questions, followed my instructions and constantly kept me updated on Bella. I would highly recommend her and will definitely use her again!”

About: I’m a lifelong dog lover with an energetic, cuddly 4-year-old goldendoodle. We enjoy daily walks, playtime, and cozy evenings. I can guarantee giving your pet loving and reliable care! ❤️ I work full time Monday-Thursday. My hubby is home during the days, and I am home during the evenings. Your dog will only be alone for 2 hours at the most during the day! I have a fenced yard and a goldendoodle to keep your fur baby company (if they enjoy dog friends!). I can easily crate your dog if needed. Always supervised safe play and calm environment.
“Amy is the best! So caring and loving to our dogs. Takes care of all of the animals needs and goes out of her way to make them happy/comfortable. The best updates and pictures. Highly recommend booking!”


“Adam was the best! My boys are super clingy and he gave them both attention. He also took the laundry back and did it all and left the house cleaner than when I left. He will definitely be a go to sitter for me.”

“Stacy took exceptional care of my dog and cat for 4 days while I was on vacation. She went above and beyond by taking my dog on extra walks, hikes, and spent a lot of time with her. I’m very happy with her care and would recommend Stacy to anyone that wants a very happy puppy to come home to!”

About: I have been around dogs and cats of all kinds my whole life. I am an experienced pet caretaker and have worked as a pet sitter and a dog daycare attendant At the moment I have flexible availability. I own quite a few cats of my own providing meals twice a day, litter box changes as well as medication and enrichment time I provide not only basic services (ie; walking, feeding) but I try to give the pets the best experience while their owners are away while giving pet parents peace of mind. I often send videos and pictures during visits as well. I will treat your pets as i would my own with any necessary responsibilities or requests.
“Jaime is great with my girls!! Her love for pets is obvious and it relieves a lot of stress knowing they’re getting their fun play time and lots of snuggles while I’m gone. I have booked her with advance notice and last minute for drop-ins and house sitting and is usually available for what I want/need.”

About: I’ve been caring for pets since I can remember and it’s truly a passion of mine. Over the past 11 + years, I’ve looked after cats, dogs, and small animals for friends, neighbors, and family. Whether it’s feeding, walking, giving medication, or just spending quality time, I treat every pet like they’re my own. I’m reliable, attentive, and always make sure your furry friend feels safe, loved, and happy while you’re away. I also keep pet parents updated with pictures and messages, so you never have to wonder how your pet is doing. I have 8 pets of my own that are all my top priority. I’m a big animal mom and know how important it is to take care of them and make sure that they are in good hands. I care for your pets by following your routine you have for them. I also keep the house tidy and will clean the liter box!

“We loved SJ and would definitely book again! SJ was extremely professional and took great care of our dog. He has anxiety so we appreciated that SJ stayed with him the whole time. She gave us updates each day and sent MANY pictures which we loved. SJ was reliable and we enjoyed the peace of mind that comes with such a professional sitter. We came home to a happy, healthy dog and a well cared for house. It was an excellent experience!”

About: What really sets me apart is the level of care and attention I give to every pet I look after. I treat each animal like my own making sure they feel safe, loved, and comfortable while their owners are away. I’m reliable, patient, and I take the time to learn each pet’s personality and routine so they get consistent care.I also have experience with puppy training helping with crate training, potty training, and basic commands as well as senior pet care, including administering medications, assisting with mobility, and providing extra comfort and attention. Whether it’s a playful puppy or an older dog who needs a gentle hand, I can adjust my care to meet their needs. Pet care fits easily into my routine since I work part-time. I have plenty of flexibility during the day and evenings to give pets the time and attention they need. Whether it’s walks, playtime, or cuddles, I make sure each pet gets consistent care and companionship throughout the week. When caring for pets in my client’s home, I do my best to keep their normal routine feeding, walks, playtime, and any special instructions so they feel comfortable and safe in their own space. I make sure they get plenty of attention, exercise, and affection while keeping their environment clean and stress free.If I’m caring for pets in my home, they’re treated just like part of the family. I provide a safe, cozy space with lots of love, play, and supervision. I always make sure they get the care, comfort, and consistency they deserve.
About: Hi, I’m Emily! I’m a lifelong animal lover with years of experience caring for dogs and cats of all ages and sizes. Whether your pet needs cuddles, playtime, or a long walk, I’ll treat them like family while you’re away. I work from home full-time and am able to work from anywhere! I have a flexible schedule that allows me to take breaks as needed to care for your furry friend. When I’m with your pet, they get my full attention. I stick closely to their routine, making sure they feel safe, loved, and stress-free. Whether it’s playtime, walks, feedings, or just quiet companionship, I tailor my care to fit each pet’s unique personality and needs. I’m patient, calm, and always alert to their comfort and well-being—because I know how important it is to feel at ease when you're away from your furry family.
“Michelle was great with Zoey. She stayed overnights for 12 days. She was amazing with Zoey and she sent me pictures and videos of her daily. She even took her for a Starbucks for the Puparchino (not sure of spelling). Will defentially use Michelle again.”
About: From trained service dog to scared abused pup we can help. I’ve trained my own service dog so I know the effort you have put in to train any pup any level. I also understand not every pup wants in my lap some just don’t want to be alone. I have also owned dogs who have limited use in their back legs to pups who have been hurt and now are scared of people. Your pups comfort comes first. If you want photos of your pup I can also do that. Memory and quieting the anxiety is important. I am currently working part time and saving up for college. I like to hang out with dogs in my free time, so taking care of your pets would be a priority. I love training pups but I can so just sit with your pup or we can play games. Walks are good for everyone as well.
How Rover works

1. Search
Read verified reviews and choose a house 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 house and 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 house sitting in Winchester is $40
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 house 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.
Sitters in Winchester average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winchester on Rover as of Dec 2025 was about $40 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Dec 2025, there are 381 house sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 17 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winchester.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winchester house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.




