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Top rated Winchester house sitters
“Samantha was amazing!! We had a graduation in Stillwater and would be gone all day. All of our fur kids loved her so much and all the pics she sent were amazing! Samantha definitely cares for your fur babies like her own. Highly recommend!”
“I really appreciated Jennifer while I was on vacation for a week! She took great care of my pup and my KitKat, giving me regular picture updates. They were played with, given outside time and treats just as I would do. Jennifer really made me feel at peace!”
“Rose was fantastic! She genuinely wanted to know about our doggos and kitties so they felt more comfortable while we were gone. She sent so many pictures, which I love, she also played with our dogs so much! She had very prompt replies and was very thoughtful during the meet and greet!”
“Beth did an amazing job taking care of our elderly dog Wu. She updated us daily with pictures of him along with how he was doing each day. It was nice to come home to a happy dog and knowing he’s been well taken care of while we were away.”
“Christian was so nice to watch our cat on short notice. We are so grateful that he was able to spend time with Meerk since she can get lonely. We would love to have him watch her again next time we need a pet sitter.”
“Jamie was great! She communicated with us and sent pictures. We were gone for a week and we came home to a clean house and a happy, healthy dog. We would definitely use her again!”
“Wonderful sitter for the pups, giving total attention to their needs. But also a very good house sitter, seeing to the cleanliness and organization of everything while we’re away.”
“Kaiya did a wonderful job of taking care of our fur babies while we were gone. She was very good at responding to communication in a timely manner. Make sure you are specific about things. I wish I had asked for pictures of my babies while we were gone. I’m used to having someone letting me see how they’re doing although they were completely fine. Overall, we were very satisfied with her and would recommend anyone using her.”
“We really liked Nik. Our dogs loved the attention and vibes from the beginning. Nik was ver attentive and communicated well. I was sent pictures at every visit and any second I even began to think about my puppies, Nik sent updates. We will be rebooking for future needs.”
“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.”
About: I’m 24! I’m new to Rover but I have loved and taken care of animals since I can remember. Worked in Shelters. I have a dog of my own who is practically my kid. I’d love to meet and hangout with your fur babies! I currently have my own cleaning company. I don’t work everyday, and this sounds like the best thing to be doing when I am not cleaning! Animals bring me so much joy. I’d make sure they are as comfortable as I can make them! Keeping them busy is very important to me and making sure they feel safe.
“We just got home to a perfectly clean house and happy animals! THANK YOU Rachel - you were communicative, responsible and loving to our home and critters, and I couldn't ask for anything more! So glad we have found you and looking forward to having you back soon!”
About: I've been working with pets for as long as I can remember! Other than the casual sitting and walking, I also have my own Australian Shepherd that I take care of. I am a college student in town, so my least busy days are Wednesdays, Fridays, and the weekend. If you need someone to stay overnight or for multiple days, I’m also available but will just have to leave a couple hours during the week for class! As someone who has had multiple pets and dogs that I've raised from puppies, I understand how important safety is when caring for animals. I am very attentive and know how to handle dangerous situations under pressure. Your pets safety is so valuable to me!
About: Im very devoted to my furry friends. I got my first dog when I was 14. She is still with me today! I currently have 3 dogs and 2 cats. I’ve always been an animal lover, before I had a dog. It was all I ever asked for. My dad told me “anytime we asked what you wanted for your birthday or Christmas it was always a dog.” I am the type of person to stop and ask to pet peoples dogs! There all so cute. Im currently working part-time at a separate job on mondays and Tuesday, im free Wednesday - Sunday, im available for potty breaks, house sitting and dog walks! I will respect your house rules, I’m very courteous. I can help with potty training, or crate training if needed. Thank you for your time.
“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!”
About: I’ve had pets my entire life and have always enjoyed taking care of them! I am very caring and will respect your pets needs! You won’t regret having someone dependable like me take care of your furry family. I work Monday through Friday 8-4:30. This leaves me available to stop by in the mornings on my way to work and also the evenings to give some much needed care! I am also fully available on the weekends to meet your needs. I am very attentive to pets and enjoy playing with them whether it be dangling a feather wand over my cats head while she jumps in the air to catch the feather, or playing fetch with my friends dogs!
Loving house sitters in your neighborhood
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Samatha C.Star Sitter
“Samantha was amazing!! We had a graduation in Stillwater and would be gone all day. All of our fur kids loved her so much and all the pics she sent were amazing! Samantha definitely cares for your fur babies like her own. Highly recommend!”
Jennifer B.Star Sitter
“Jennifer did a great job with our Maggie. She was punctual, professional, left my home clean, and was very communicative. I would highly recommend!”
jennifer b.
“I really appreciated Jennifer while I was on vacation for a week! She took great care of my pup and my KitKat, giving me regular picture updates. They were played with, given outside time and treats just as I would do. Jennifer really made me feel at peace!”
Rose S.
“Rose was fantastic! She genuinely wanted to know about our doggos and kitties so they felt more comfortable while we were gone. She sent so many pictures, which I love, she also played with our dogs so much! She had very prompt replies and was very thoughtful during the meet and greet!”
Elizabeth K.
“Beth did an amazing job taking care of our elderly dog Wu. She updated us daily with pictures of him along with how he was doing each day. It was nice to come home to a happy dog and knowing he’s been well taken care of while we were away.”
Christian E.Star Sitter
“Christian was so nice to watch our cat on short notice. We are so grateful that he was able to spend time with Meerk since she can get lonely. We would love to have him watch her again next time we need a pet sitter.”
Jamie W.Star Sitter
“Jamie was great! She communicated with us and sent pictures. We were gone for a week and we came home to a clean house and a happy, healthy dog. We would definitely use her again!”
Stacey F.Star Sitter
“Wonderful sitter for the pups, giving total attention to their needs. But also a very good house sitter, seeing to the cleanliness and organization of everything while we’re away.”
Kaiya D.
“Kaiya did a wonderful job of taking care of our fur babies while we were gone. She was very good at responding to communication in a timely manner. Make sure you are specific about things. I wish I had asked for pictures of my babies while we were gone. I’m used to having someone letting me see how they’re doing although they were completely fine. Overall, we were very satisfied with her and would recommend anyone using her.”
Nikki C.Star Sitter
“We really liked Nik. Our dogs loved the attention and vibes from the beginning. Nik was ver attentive and communicated well. I was sent pictures at every visit and any second I even began to think about my puppies, Nik sent updates. We will be rebooking for future needs.”
Diane A.
“Found the dog happy as ever when we returned. She was fed and let out at the time requested.”
Ryan R.
“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.”
Immajen B.
“Our dog Lucy absolutely loves Immajen. She literally cries and wags her tail if we mention her name around our house now! Immajen is a natural with animals. You can tell she adores them and connects with them easily. We always know our pup is in good hands with her!”
Ariel G.
“She took great care of my sweet girl! Very easy to communicate with and quick response time. Sent picture updates that made me feel very comfortable with her care!”
Rachel K.Star Sitter
“We just got home to a perfectly clean house and happy animals! THANK YOU Rachel - you were communicative, responsible and loving to our home and critters, and I couldn't ask for anything more! So glad we have found you and looking forward to having you back soon!”
Elle S.
About: I've been working with pets for as long as I can remember! Other than the casual sitting and walking, I also have my own Australian Shepherd that I take care of. I am a college student in town, so my least busy days are Wednesdays, Fridays, and the weekend. If you need someone to stay overnight or for multiple days, I’m also available but will just have to leave a couple hours during the week for class! As someone who has had multiple pets and dogs that I've raised from puppies, I understand how important safety is when caring for animals. I am very attentive and know how to handle dangerous situations under pressure. Your pets safety is so valuable to me!
Ashlynn F.
“Ashlynn is just beloved by the many dogs she cares for specially my boy Fido. Dogs love her so much she once saved a strangers dog running wild on nyc streets with her loving and endearing voice alone . She's like a dog whisperer !”
aspen h.
“Aspen did a great job watching all of my crazy kids. She kept me up to date on how everything was going through the status, and you can really tell she is am animal lover at heart”
Amy M.
“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!”
Emily H.
About: I’ve had pets my entire life and have always enjoyed taking care of them! I am very caring and will respect your pets needs! You won’t regret having someone dependable like me take care of your furry family. I work Monday through Friday 8-4:30. This leaves me available to stop by in the mornings on my way to work and also the evenings to give some much needed care! I am also fully available on the weekends to meet your needs. I am very attentive to pets and enjoy playing with them whether it be dangling a feather wand over my cats head while she jumps in the air to catch the feather, or playing fetch with my friends dogs!
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!
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.
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 Aug 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 Aug 2025, there are 375 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, 91% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 18 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.
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