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Top rated Winchester house sitters
“Alexsys was wonderful with Bailey! When I had a recent family emergency with my daughter going into labor three weeks early, I had town quickly. Alexsys jumped right in and took great care of Bailey, sending pictures and updates that really helped me feel comfortable leaving my furbaby. I would definitely book her again!”
“Charissa was amazing, daily photos of our cat, she was well taken care of and the communication was impeccable. Would highly recommend and use again.”
“Kathy is a true gem. We had complete peace of mind while she house sat our three Lab rescues. Kathy is dependable, communicative, and takes care of your house and pets like they are her own. We will absolutely be booking her again.”
“Steven is amazing! Reliable, communicative, and very thoughtful. Our cats were comfortable and immediately warmed to him. I would enthusiastically recommend Steven to anyone who needs great pet care.”
“Alex really helped me out short notice and over a holiday!! She provided personalized care and is very knowledgeable. I knew my high-energy pup was in good hands :) i loved the photos / vid updates — will def reach out again!”
About: My name is Sadie. I am an 20 year-old, third year, at Shenandoah University. I love hanging around dogs, cats, or honestly any animal. I have been exposed to all types of animals from farm to regular housepets. I was raised living with a cat and taking care of chickens. I also would help out neighbors with watching their pets; started doing so around the age of 12. I have quite a few experiences under my belt with dogs ranging from 5 month olds through veterans. My dog is an American Pitbull Terrier and is now 3 years old. I love him and any animal I am responsible for with all I have. When I am home from school, I am more than likely open to any schedule. Most likely what works for you, will work for me! As of right now, I do have another part-time, low hour job and internship. Even with those two, I have plenty of free time to come help you with your pets! Your pets will be cared for by me just as much as you do for them. I am a hard worker who will always give 110% into caring for your pets. Whatever you ask of me to do, I will do my best to complete to your and your pets' satisfaction. I also will provide you with pictures and updates whenever your pets and I do anything.
About: Have had dogs all my life. Love them and they love me! Long walks and dog parks, if allowed, plus all the belly rubs and treats! Currently nannying and going back to school. Have a very flexible schedule and available at most times during the day and evening for walks or drop ins. I like to meet your fur babies first to make sure it’s a good fit for both of us. Discuss behavior and tendencies. Happy to go on walks, let them out, hangout and play.
“Maddie was so sweet, reliable, and took great care of our pups. We will absolutely be using her again!”
“Carse provided terrific care for our pups!”
“Roxana took very good care of Allie for the week!”
“Ashley did an outstanding job of taking care of our Pupper while we gone for the weekend. She gave detailed updates throughout those couple of days and sent us photos! I highly recommend her services if you need someone professional, responsible and will take of your pups like her own.”
“Mary was wonderful! She took care of Pippa for a week! I will definitely be asking her back. She kept me posted with pictures and videos. When the power flickered and caused the AC to go out, she tried troubleshooting, and then dealt with the electrician and HVAC tech. I felt very good wirh Mary yaking care of that and Pippa too!”
“Sabrin was great! She typically doesn’t do large size dogs, but she decided to meet mine and he loves her. My Pomsky is usually stressed and can be standoff but she went straight to Sabrin and begged for attention. My cat (willow) who usually stays away from strangers but came out to greet Sabrin and even allowed Sabrin to pick her up. I was very pleased with Sabrin and how flexible she was with my sudden change in vacation days/times. I highly recommend and will be asking for her services again! Thank you Sabrin:)”
“Carter did a fantastic job watching our 2 dogs and cat for the weekend. He kept us up to date and sent photos. They were well-tended and happy when we got back, and house was as we left it! Highly recommend Carter!”
About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)
“Gabe did a great job!”
About: -About Me- I've had 10+ years experience in doggy care! I've delivered puppies at the age of 15 and worked close to my parents and their vet business all my life. I love dogs of all sizes and breeds. Caring for them is second nature for me :) I've fostered several dogs over the past three years. -My Motto- I can offer you relief knowing that your pup is being taken care of by an experienced and genuinely loving caretaker! - Doggies Love Excercise - On our walk I will provide your pup with some workouts and toys to ensure he/she has the best walk of their life! I am very honored and excited to get to know your fur baby! Book your appointment today! i’m currently working fully remote so rest assured you pet will be 100% taken care of 100% of the time. We have an amazing dog park near by and lots of trails for your fur babies to explore! i have many nature trails and a doggy park nearby so you can rest peacefully knowing your pup will definitely get some exercise under my care, fed on their regular schedule and given all the pets they want.
“This was our first time with Rover, and I have to say, we picked the BEST dog sitter the first time! Claire was amazing! I knew from our initial meeting that she was the perfect sitter for our girls, and she absolutely was! We have two middle-aged, rescue, Bichon Frise girls and their "ways" can be a bit difficult for some, but Claire took it on, and we couldn't be happier! She is friendly and kind and patient. She sent us photos and updates from the beginning. I didn't worry one bit about the girls or the house for the three full days and two nights that we were gone! If I could give her MORE stars on Rover, I would! We have found our dog sitter!! Thank you Claire!!! :)”
“Alex did a great job taking care of our fur babies. He didn't hesitate to reach out to us if he had questions and kept us well informed how the pups were doing.”
About: I love working with animals! I have years of experience caring for animals between pet sitting and shelter work. I have experience bathing, grooming pets, determining daily food portions, walking dogs, providing companionship, and administering medicine. I find caring and being around animals on a regular basis to be very rewarding. I work full-time Monday-Thursday. I am available as early as 6:00am-5:00pm Friday, Saturday, and Sunday. I can be flexible to you and your pet/pets needs. I will ensure your pet/pets receive love, affection, and adequate time will be given for their care. Depending upon your pet/pets needs, long walks, play time, ect.
Loving house sitters in your neighborhood
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1. Alexsys T.
“Alexsys was wonderful with Bailey! When I had a recent family emergency with my daughter going into labor three weeks early, I had town quickly. Alexsys jumped right in and took great care of Bailey, sending pictures and updates that really helped me feel comfortable leaving my furbaby. I would definitely book her again!”
2. Charissa L.
“Charissa was amazing, daily photos of our cat, she was well taken care of and the communication was impeccable. Would highly recommend and use again.”
3. Kathy G.
“Kathy is a true gem. We had complete peace of mind while she house sat our three Lab rescues. Kathy is dependable, communicative, and takes care of your house and pets like they are her own. We will absolutely be booking her again.”
4. Steven F.
“Steven is amazing! Reliable, communicative, and very thoughtful. Our cats were comfortable and immediately warmed to him. I would enthusiastically recommend Steven to anyone who needs great pet care.”
5. Alex K.
“Alex really helped me out short notice and over a holiday!! She provided personalized care and is very knowledgeable. I knew my high-energy pup was in good hands :) i loved the photos / vid updates — will def reach out again!”
6. Sadie S.
“Sadie has been wonderful to work with, taking care of our fur babies. She is super reliable and trustworthy. She listens to our needs & instructions and asks questions to ensure we both are on the same page. She communicates throughout the "sitting" period keeping us informed of our fur babies well-being or challenges that may arise. And...I love the photos of her and the babies having fun. Sadie is the best!!”
7. Shannon B.
“Shannon is the absolute best. Our entire family is pretty sure our dog Scott loves her more than any of us lol. She’s very dependable and she’s so great with Scott. She’s our first call if we have to go out of town and we need someone who will take incredible care of our dog, because we know she loves him as much as we do.”
8. Maddie E.
“Maddie was so sweet, reliable, and took great care of our pups. We will absolutely be using her again!”
9. Carse R.
“Carse provided terrific care for our pups!”
10. Roxana N.
“Roxana took very good care of Allie for the week!”
11. Ashley R.
“Ashley did an outstanding job of taking care of our Pupper while we gone for the weekend. She gave detailed updates throughout those couple of days and sent us photos! I highly recommend her services if you need someone professional, responsible and will take of your pups like her own.”
12. Mary M.
“Mary was wonderful! She took care of Pippa for a week! I will definitely be asking her back. She kept me posted with pictures and videos. When the power flickered and caused the AC to go out, she tried troubleshooting, and then dealt with the electrician and HVAC tech. I felt very good wirh Mary yaking care of that and Pippa too!”
13. Sabrin W.
“Sabrin was great! She typically doesn’t do large size dogs, but she decided to meet mine and he loves her. My Pomsky is usually stressed and can be standoff but she went straight to Sabrin and begged for attention. My cat (willow) who usually stays away from strangers but came out to greet Sabrin and even allowed Sabrin to pick her up. I was very pleased with Sabrin and how flexible she was with my sudden change in vacation days/times. I highly recommend and will be asking for her services again! Thank you Sabrin:)”
14. Carter J.
“Carter did a fantastic job watching our 2 dogs and cat for the weekend. He kept us up to date and sent photos. They were well-tended and happy when we got back, and house was as we left it! Highly recommend Carter!”
15. Stefany P.
About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)
16. Gabe E.
“Gabe did a great job!”
17. Maribeth T.
“Maribeth is one of the most wonderful people to come across when it comes to dog care. You can definitely tell she has a passion for animals. Her presence makes you feel comfortable and relieved knowing you can leave your dog with someone so trusting. She really treats your dog like family, thank you Maribeth you rock !!”
18. Claire Z.
“This was our first time with Rover, and I have to say, we picked the BEST dog sitter the first time! Claire was amazing! I knew from our initial meeting that she was the perfect sitter for our girls, and she absolutely was! We have two middle-aged, rescue, Bichon Frise girls and their "ways" can be a bit difficult for some, but Claire took it on, and we couldn't be happier! She is friendly and kind and patient. She sent us photos and updates from the beginning. I didn't worry one bit about the girls or the house for the three full days and two nights that we were gone! If I could give her MORE stars on Rover, I would! We have found our dog sitter!! Thank you Claire!!! :)”
19. Alex H.
“Alex did a great job taking care of our fur babies. He didn't hesitate to reach out to us if he had questions and kept us well informed how the pups were doing.”
20. Taylor S.
About: I love working with animals! I have years of experience caring for animals between pet sitting and shelter work. I have experience bathing, grooming pets, determining daily food portions, walking dogs, providing companionship, and administering medicine. I find caring and being around animals on a regular basis to be very rewarding. I work full-time Monday-Thursday. I am available as early as 6:00am-5:00pm Friday, Saturday, and Sunday. I can be flexible to you and your pet/pets needs. I will ensure your pet/pets receive love, affection, and adequate time will be given for their care. Depending upon your pet/pets needs, long walks, play time, ect.
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 May 2025 was about $45 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 May 2025, there are 302 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, 87% 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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