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.
“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.”

“Jennifer sent me pictures of my dogs while we were gone and told me how they were doing which I really appreciated. Her communication was very professional and timely. She kept my home very clean while we were gone. I would recommend Jennifer to watch your dogs.”

“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: 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!!!

“SJ did a great job of keeping me updated about my babies. I got lots of pictures and she let me know if the babies ate or not. I will book her again without hesitation. My husband and I have put off vacations because of our dogs and their quirky dispositions but SJ was wonderful!”

About: I’ve trained 3 dogs to be pet pals. I have had and cared for dogs my whole life. I have cared for puppies to senior dogs and have experience administering medication to elderly dogs. I am currently in college so I have plenty of time to care for pets! I am available to house sit or walk dogs as needed! I am able to crate dogs if needed and have experience dealing with multiple dogs. I also have experience with food aggression and other special needs.

About: I’ve always taken care of pets whether they were mine, or someone who needed a sitter for the weekend! Pets are our babies as well! I’m currently between jobs, and have more than enough time in my life right now, and would love to take care of your fur babies! We have 5 acres for them to play on! I have two of my own dogs, who are little social butterflies. They would gladly take on some new friends!

About: I’ve cared for pets for many years and genuinely enjoy spending time with animals of all sizes and personalities. Friends, family, and neighbors have trusted me to feed, walk, play with, and care for their pets while they were away. I understand that every pet has unique needs, and I take the time to make them feel safe, comfortable, and loved. Whether your pet needs exercise, companionship, medication reminders, or extra attention, I provide dependable care and regular updates so you can have peace of mind while you’re away. I currently work nights on the weekends and amd willing to take crate-trained animals while I'm gone. I only work 3 nights a week so I am free most of the week I have a fenced in yard on 5 acres with a house that is 1500 sq ft. I don't have any other animals. I want to make your animal feel at home and take the best care of them as possible
“I reached out to Francine on Rover and she was quick to respond with her availability. She made the effort to meet my dog before we left for vacation when i told her that hes a rescue and takes sometime to open up. She was punctual, communicative and had a lot of patience with my dog. Finally on day 3, he opened up to her! She kept the house neat and clean as well. Thank you Francine for taking care of my dog. I appreciate your time and patience with him. Will definitely be rebooking! Don’t hesitate to leave your pets in her care!”

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.
“5/5 — Absolutely Amazing Experience with Rose! Rose was incredible! She took care of our pets for two weeks and went above and beyond every single day. She sent multiple updates and photos daily, which gave us so much peace of mind while we were away. She followed my detailed written instructions perfectly and made sure everything was done exactly as requested. Not only is Rose professional and trustworthy, but she’s also thoughtful — she left our home spotless before she left! It’s clear she truly cares about the animals she watches and treats them like her own. I can’t recommend her highly enough to anyone looking for a reliable and compassionate sitter. We’ll absolutely be booking with her again!”

“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!”

“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: I’ve been a dog owner ever since I can remember, I’m a small town farm boy turned insurance agent. My weekends are generally free for the most part as my kids are grown, so I’d love to watch critter kids when you need me. I am an insurance agent during the week. My weekends are available to house and pet sit. I recently lost the love of my life, my corgi Sadie. So, I would love to help with your furry kids. I don't currently live where I can keep your pets at my place, but I will gladly take care of your furry kids at their home.
About: I have worked with horses as a teenager. And look after pets for a neighbor, family, and friends. I have a friendly dog that loves to play with other pets. Have watched puppies and senior. Right now I am at home full time so can have pets anytime and any day of the month. And have a car to drive. And have not met a dog that didn't like me. I a big front yard and backyard, have a big dog house outside, have a open living room and kitchen so have enough room for pets to move around and play. And I own a dog who is very friendly with other pets. And my yard is treated so pets don't need to worry about pests.
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.
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 Jun 2026 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 Jun 2026, there are 368 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, 93% 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.




