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Top rated Winchester house sitters
“Alana was once again amazing with my pup! She followed all of the instructions I left and kept me in the loop during her time with Tyson. She also sent me pictures while I was gone. I highly recommend her!”
“We had Rachael house sit and stay with our dog for a weekend while my husband and I were out of town. Rachael took great care of Pepper and our house was in great shape when we got home! Will definitely book the next time we need a sitter. Thanks Rachael!”
“Natalie was amazing. She took great care of my older cat, anticipating what he needed to be more comfortable. She sent updates and photos regularly and left the house clean and neat. Highly recommend!”
“Amanda is great. She took excellent care of my cats and bird while house sitting for a couple days. She let now how everyone was doing daily with pics. I’ll for sure be having her back! Thanks so much Amanda.”
“Andrew stayed for a week+ with our rescue hound mix, Jack, and was awesome—- he sent me 2 photos a day, is very responsive to messages and left us with a clean house and happy dog! Thanks, Andrew.”
“Nicole was excellent on her services. She stayed in our apartment for a house visit and she was super respectful of the place. She was very effective in communication and I was never wondering what our dog was up to, since Nicole planned out several activities and outings. I’m 100% hoping to re-book her for any future needs.”
“Jasmine is fantastic! She took such great care of my dog Beau. She watched him at my home, was very attentive to his needs and took great care of my home as well. She was very easy to communicate with throughout the stay and very responsive. I would highly recommend Jasmine!”
“Fahad was fantastic! We felt immediately comfortable with him from our first meet and greet. He stayed in our home with our young and energetic dog and an our cat for a little over a week. He sent lots of updates and took such great care of them both! Would definitely recommend Fahad for your pet sitting needs!”
“Aaron was great and easy to connect with for a day of watching our big dog. Grateful he was open to a meet and greet first and updated throughout the time he was watching our boy 🐶”
“Christine was lovely with Bonnie. She spoiled her and I felt very comfortable leaving Bonnie in her care. She has a natural gift with dogs and just loves to be around them. Absolutely happy with Christine”
About: With 6 years of pet care experience, I provide dependable, loving attention to pets of all ages. I’m comfortable with walks, feeding, playtime, and giving extra patience to senior pets. My priority is keeping pets safe, happy, and cared for as if they were my own. I work full-time in an office but have flexibility to accommodate different pet care needs, including evenings and weekends. Happy to discuss a schedule that works best for you and your pet. I care for pets in the comfort of their own home, where they feel safest. With a long-standing record of looking after both dogs and cats, I ensure they receive attentive, loving care while you’re away. I respect your home, follow your routines, and prioritize your pet’s well-being at all times.
“Carly was awesome! She was super communicative and flexible when she stayed at our apartment for the weekend. Our pup is a tad reactive and Carly knew how to take care of him, and he loved her! We came back to a very happy dog and will definitely be booking her again. She also left our house very clean. Thanks, Carly!”
“From first contact Rhianna was an A+. She's caring, communicative, and so easy to coordinate with. This was my first experience using Rover and she patiently helped with every step of the logistics when I had trouble with the app. She is responsive, asks great questions, and is extremely kind and capable. Our dog injured her leg just before we went away and Rhianna didn't hesitate to step up with extra care to make sure she stayed safe and happy. The photos she sent us tell the story so clearly: Henry and Lulah were in great hands and can't wait for Rhianna - their new favorite person - to come back soon!”
“Highly recommend Matthew to sit your pets! He is a very communicative, reliable and caring sitter. He asked thoughtful questions and sent tons of pictures. He put my mind at ease while I was away from my pups 😊”
Loving house sitters in your neighborhood
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Jupiter B.Star Sitter
“Jupiter did a great job. The house was clean and orderly when we returned, and the dogs were content.”
Alana C.Star Sitter
“Alana was once again amazing with my pup! She followed all of the instructions I left and kept me in the loop during her time with Tyson. She also sent me pictures while I was gone. I highly recommend her!”
Rachael B.Star Sitter
“We had Rachael house sit and stay with our dog for a weekend while my husband and I were out of town. Rachael took great care of Pepper and our house was in great shape when we got home! Will definitely book the next time we need a sitter. Thanks Rachael!”
Natalie J.Star Sitter
“Natalie was amazing. She took great care of my older cat, anticipating what he needed to be more comfortable. She sent updates and photos regularly and left the house clean and neat. Highly recommend!”
Amanda P.Star Sitter
“Amanda is great. She took excellent care of my cats and bird while house sitting for a couple days. She let now how everyone was doing daily with pics. I’ll for sure be having her back! Thanks so much Amanda.”
Andrew T.Star Sitter
“Andrew stayed for a week+ with our rescue hound mix, Jack, and was awesome—- he sent me 2 photos a day, is very responsive to messages and left us with a clean house and happy dog! Thanks, Andrew.”
Nicole T.
“Nicole was excellent on her services. She stayed in our apartment for a house visit and she was super respectful of the place. She was very effective in communication and I was never wondering what our dog was up to, since Nicole planned out several activities and outings. I’m 100% hoping to re-book her for any future needs.”
Jasmin L.Star Sitter
“Jasmine is fantastic! She took such great care of my dog Beau. She watched him at my home, was very attentive to his needs and took great care of my home as well. She was very easy to communicate with throughout the stay and very responsive. I would highly recommend Jasmine!”
Fahad S.Star Sitter
“Fahad was fantastic! We felt immediately comfortable with him from our first meet and greet. He stayed in our home with our young and energetic dog and an our cat for a little over a week. He sent lots of updates and took such great care of them both! Would definitely recommend Fahad for your pet sitting needs!”
Lacie S.Star Sitter
“Lacie sat with our dog for one evening. When we returned, our dog was happy and fed and walked and played with. We would ask Lacie to sit for us again.”
Jolene G.
“Great first experience with Rover! Jolene was terrific!”
Aaron G.
“Aaron was great and easy to connect with for a day of watching our big dog. Grateful he was open to a meet and greet first and updated throughout the time he was watching our boy 🐶”
Justin J.
“Justin was great to work with! He sat our dog, Mouse, in our home. He clearly communicated with us and was very professional. Would recommend.”
Christine C.
“Christine was lovely with Bonnie. She spoiled her and I felt very comfortable leaving Bonnie in her care. She has a natural gift with dogs and just loves to be around them. Absolutely happy with Christine”
James T.Star Sitter
“James was very loving, enthusiastic and super caring for our puppy Hugo. HIGHLY recommend! 5 stars!”
Timothy O.
“Timothy has been a wonderful and loving pet caregiver to my cat on multiple occasions. Reliable, responsible and trustworthy, highly recommend to anyone looking for a pet caregiver!”
Natasha B.
“Natasha is wonderful. Responsible and a true dog person.”
Carly D.
“Carly was awesome! She was super communicative and flexible when she stayed at our apartment for the weekend. Our pup is a tad reactive and Carly knew how to take care of him, and he loved her! We came back to a very happy dog and will definitely be booking her again. She also left our house very clean. Thanks, Carly!”
Rhianna S.
“From first contact Rhianna was an A+. She's caring, communicative, and so easy to coordinate with. This was my first experience using Rover and she patiently helped with every step of the logistics when I had trouble with the app. She is responsive, asks great questions, and is extremely kind and capable. Our dog injured her leg just before we went away and Rhianna didn't hesitate to step up with extra care to make sure she stayed safe and happy. The photos she sent us tell the story so clearly: Henry and Lulah were in great hands and can't wait for Rhianna - their new favorite person - to come back soon!”
Matthew C.
“Highly recommend Matthew to sit your pets! He is a very communicative, reliable and caring sitter. He asked thoughtful questions and sent tons of pictures. He put my mind at ease while I was away from my pups 😊”
Over 115 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
Natalie did an amazing job from start to finish, excellent communicator, sent tons of pictures, followed our guidance on caring for our cat perfectly. She was punctual, conscientious, and clearly a lover of cats. Would highly recommend without reservation. A true gem.
Ayat is a lovely and attentive sitter! She was super communicative with me the whole time, and did an excellent job taking care of my dog Loki. He clearly had so much fun whole I was gone! She was even willing to accommodate his silly little quirks like wanting to be picked up, even though he is 35lbs :) I would definitely recommend her, and will be booking with her again!
Greg has cared for Cleo many times—from afternoon dog walks to weekend overnights to staying with her for weeks. Greg truly cares for pets as if they are his own relatives! No one will ask you more thorough questions about your pet's behaviors, needs, and personality, or send you more detailed, loving updates throughout the stay. We love having Greg watch Cleo and feel so lucky to have him in our lives!
Martin was great with our two dogs and one cat. He was very communicative and was patient when one of my dogs was not allowing him to put on his harness. He kept trying and was successful eventually. There was a misunderstanding the first night about staying over but Martin addressed it and all was well for the rest of the visit.
Eunae is wonderful! She recently stayed a long-weekend with my active, 3.5 year old Australian Shepard and he completely fell in love. She was caring and attentive to my pup, while being so considerate of his routine and our home. She went the extra mile to even practice tricks and training, pull out his puzzles, and make it a fun, enriching environment for our dog. Eunae has excellent communication with us while we were out of town; we received photos and texts updating us on how the pup was doing multiple times a day. This was the first time I’ve left my dog in someone else’s care and I would trust Eunae again in a heartbeat. I can’t recommend her enough!
Maria did so great with Mouse! Unfortunately, Mouse got into some of her allergy medicine while Maria was sitting her (not Maria's fault at all!). Maria was quick to communicate with us and coordinated with us to make sure we could get Mouse to a nearby vet. Mouse is doing great and we really appreciated Maria's responsiveness and communication.
Catherine was amazing to work with - she is warm and friendly to both people and pets and communicated well. The house was just as we left it and the dog was clearly happy and well cared for upon our return. We would not hesitate to book with Catherine again, and would recommend her without reservation.
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 $60
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 3 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 Aug 2025 was about $60 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 5,745 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, 84% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 14 years of experience. House sitters with repeat customers have an average of 3 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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