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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.
“Joanna is WONDERFUL!!!!! I can't say enough about her in this brief spot. My two girls loved her, and so did i! Her kindness is above and beyond! If she stays on rover, I will definitely be reaching out again! Anyone who books with her, will not be disappointed!”
“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.”
“My dog greeted Alex with absolute joy, so I know that Alex treated her well the last time she was here. Alex is reliable, communicative, and a true canine professional. She even provided me with a tip for a trainer who could help Farah with her reactivity to other dogs.”
“Emily did a fantastic job once again taking care of our dog Rocky. She sent so many cute pictures and videos. She took Rocky on a walk and brushed him! Rocky always looks like he's having a blast when Emily is around!”
About: Hi my name is DaVion! Caring for others is second nature to me—whether it’s people or pets. I have hands-on experience with animals and truly enjoy spending time with them. I offer dog walking, feedings, drop-in visits, and fun playtime. I understand how important it is to have someone reliable and caring looking after your pet, and I’m happy to work around your schedule to make things easy and stress-free. Whether it’s an energetic pup or a laid-back senior pet, I’m here to give them the attention, affection, and care they deserve. Your pet’s comfort and safety are always my priority. Let me know how I can help! I am a full time college student. My schedule stays daily consistent and I am proactive about any changes Mon-Wed 3p-10p Thur 4:30p-10p Sat & Sun Appointment based I can come to your home and provide any pet care you may need! I am ok with any time of environment as long as there are directions
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 :)
About: I absolutely love animals and would consider it an honor to care for your furry family members when the need arises. I worked as a part-time pet and house sitter for 3 plus years in Northern Virginia and only stopped when I moved to Stephens City. I am looking forward starting up again to earn a little extra income. I am experienced in house sitting as well. Feel free to contact me with any questions.
“Excellent and will definitely book again. Sierra was great, communicated really well and treated my dogs fantastically. Had no problems with the initial meet and greet, fabulous all around , and both dogs really seemed to love her”
“Megan is an absolute treasure!! And that’s with a T not a P. Although she was also a pleasure to work with she is one of the most capable, friendly, caring, conscientious, pet sitters I have ever met. I will definitely use her again. I say treasure because she’s the sitter I would want again and again and again. 10/10 🥰🥰”
“Julia is wonderful with our cat and taking care of our home while we are out of town. She kept us up-to-date throughout each day with photos and even a video of our little guy. She was very prompt and great at communication. Thank you so much, Julia!”
“Alexsys, was wonderful in communication and relating to our pets. We came home to happy doggies and a clean house. I highly recommend Alexsys! Shirls & Craig Hall (Ceasar & Lacy)”
About: I have experience aid medical and grooming any breeds. I do have so many patients for any pets. I always come up new ways to make sure they enjoy their fun games I work part time on weekdays so I am available certain holidays and weekends. If you have any questions or certain about your baby feel free left me a messages I have fenced yard and there is grooming room if your pet decides to get smelly even dirty coat. One my siblings does own 6 dogs if you choose to play date :)
“Cassie did a great job caring for my pups! She was attentive and clearly has a genuine love for animals. I especially appreciated the photo and video updates she sent throughout the stay, as well as her proactive communication regarding any concerns. My only feedback is to kindly ask that sitters closely follow the established routine for feeding and potty breaks, as consistency is important for my pups. Overall, Cassie was reliable, communicative, and very sweet with the dogs—I would definitely consider booking her again.”
“Mary was so great with my three legged dog and my cat. She was communicating with me the entire time I was away, along with pictures and updates. I was able to enjoy my weekend because I wasn't worrying about my fur babies back home the entire time. Would recommend to a friend ✨️”
About: I have been caring for friends and neighbors dogs, cats, and small animals since i was 13. I also volunteer at the PWC Animal Shelter! I am an incoming first year college student starting at Shenandoah University in the fall, i currently have a lot of availability all day, every day! I have a clean house and a large dog crate if you would like me to crate your dog, i have a friendly golden retreiver and two cats who are all great with other animals.
About: I've trained dogs in my teenage years, and l've over puppies and kittens as well as lizards let me care for your pets while you relax. We’re a very organized couple and that allows us to have a well put together schedule. willing to always be flexible and tend to our pets easily! We have a dog park that’s a lovely drive away from the house! We love to play, take naps and match the pets moods and let them enjoy being themselves comfortably! And pet safety is a big deal! No wandering off and no biting or getting bitten of course haha
About: My name is Sadie. I am an 20 year-old, graduate student, 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: Hi my name is Jonathan I have a dog and cat of my own. I’m willing to walk, hangout, and chill with your pet to fulfill their happiness. I’m currently not working but in the future will be working full-time. So right now I have plenty of time to hangout with your pups! I have a fenced in yard and one friendly dog to keep your fur baby company. I’m also willing to crate your dog if needed
Loving house sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Joanna S.
“Joanna is WONDERFUL!!!!! I can't say enough about her in this brief spot. My two girls loved her, and so did i! Her kindness is above and beyond! If she stays on rover, I will definitely be reaching out again! Anyone who books with her, will not be disappointed!”
Kathy G.Star Sitter
“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.”
Alex K.
“My dog greeted Alex with absolute joy, so I know that Alex treated her well the last time she was here. Alex is reliable, communicative, and a true canine professional. She even provided me with a tip for a trainer who could help Farah with her reactivity to other dogs.”
Emily F.Star Sitter
“Emily did a fantastic job once again taking care of our dog Rocky. She sent so many cute pictures and videos. She took Rocky on a walk and brushed him! Rocky always looks like he's having a blast when Emily is around!”
Hannah U.
“Hannah jumped in at the last minute to watch our two dogs and did a great job keeping me informed with their status. I would definitely recommend her”
DaVion P.
About: Hi my name is DaVion! Caring for others is second nature to me—whether it’s people or pets. I have hands-on experience with animals and truly enjoy spending time with them. I offer dog walking, feedings, drop-in visits, and fun playtime. I understand how important it is to have someone reliable and caring looking after your pet, and I’m happy to work around your schedule to make things easy and stress-free. Whether it’s an energetic pup or a laid-back senior pet, I’m here to give them the attention, affection, and care they deserve. Your pet’s comfort and safety are always my priority. Let me know how I can help! I am a full time college student. My schedule stays daily consistent and I am proactive about any changes Mon-Wed 3p-10p Thur 4:30p-10p Sat & Sun Appointment based I can come to your home and provide any pet care you may need! I am ok with any time of environment as long as there are directions
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 :)
Sherry R.
About: I absolutely love animals and would consider it an honor to care for your furry family members when the need arises. I worked as a part-time pet and house sitter for 3 plus years in Northern Virginia and only stopped when I moved to Stephens City. I am looking forward starting up again to earn a little extra income. I am experienced in house sitting as well. Feel free to contact me with any questions.
Sierra B.
“Excellent and will definitely book again. Sierra was great, communicated really well and treated my dogs fantastically. Had no problems with the initial meet and greet, fabulous all around , and both dogs really seemed to love her”
Megan S.
“Megan is an absolute treasure!! And that’s with a T not a P. Although she was also a pleasure to work with she is one of the most capable, friendly, caring, conscientious, pet sitters I have ever met. I will definitely use her again. I say treasure because she’s the sitter I would want again and again and again. 10/10 🥰🥰”
Julia Z.
“Julia is wonderful with our cat and taking care of our home while we are out of town. She kept us up-to-date throughout each day with photos and even a video of our little guy. She was very prompt and great at communication. Thank you so much, Julia!”
Alexsys T.Star Sitter
“Alexsys, was wonderful in communication and relating to our pets. We came home to happy doggies and a clean house. I highly recommend Alexsys! Shirls & Craig Hall (Ceasar & Lacy)”
Marlene C.
About: I have experience aid medical and grooming any breeds. I do have so many patients for any pets. I always come up new ways to make sure they enjoy their fun games I work part time on weekdays so I am available certain holidays and weekends. If you have any questions or certain about your baby feel free left me a messages I have fenced yard and there is grooming room if your pet decides to get smelly even dirty coat. One my siblings does own 6 dogs if you choose to play date :)
Alexandria Y.
“Took great care of my dogs when I was out of town and very responsive the entire time! Would recommend Alexandria to anyone!”
Cassie J.
“Cassie did a great job caring for my pups! She was attentive and clearly has a genuine love for animals. I especially appreciated the photo and video updates she sent throughout the stay, as well as her proactive communication regarding any concerns. My only feedback is to kindly ask that sitters closely follow the established routine for feeding and potty breaks, as consistency is important for my pups. Overall, Cassie was reliable, communicative, and very sweet with the dogs—I would definitely consider booking her again.”
Mary M.
“Mary was so great with my three legged dog and my cat. She was communicating with me the entire time I was away, along with pictures and updates. I was able to enjoy my weekend because I wasn't worrying about my fur babies back home the entire time. Would recommend to a friend ✨️”
charlotte g.
About: I have been caring for friends and neighbors dogs, cats, and small animals since i was 13. I also volunteer at the PWC Animal Shelter! I am an incoming first year college student starting at Shenandoah University in the fall, i currently have a lot of availability all day, every day! I have a clean house and a large dog crate if you would like me to crate your dog, i have a friendly golden retreiver and two cats who are all great with other animals.
Christopher P.
About: I've trained dogs in my teenage years, and l've over puppies and kittens as well as lizards let me care for your pets while you relax. We’re a very organized couple and that allows us to have a well put together schedule. willing to always be flexible and tend to our pets easily! We have a dog park that’s a lovely drive away from the house! We love to play, take naps and match the pets moods and let them enjoy being themselves comfortably! And pet safety is a big deal! No wandering off and no biting or getting bitten of course haha
Sadie S.
“Sadie has taken care of our needy, spoiled bulldog in the past and now takes care of our 2 rescue dogs. One is a fox hound and the other is a aussie mix. If the dogs are special needs and needs have special instructions, Sadie is your girl. At the end for our bulldog she was always on time for meds and potty walks.”
Jonathan M.
“Jonathan is super reliable and great with animals. Jonathan is very experienced and will love on your pets like they are his own! I highly recommend Jonathan as a dependable pet sitter!”
Over 441 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
We couldn’t have asked for a better sitter. Mary house sit for us for two weeks while we’re on vacation. Not only did she take care of our baby girl - food, walks, meds, etc. but also helped manage the house while we were away. I would highly recommend her services and will be contacting her again for our next trip! 5⭐️
Kathy G was awesome with our pups while we were gone. She sent updates, pictures and more every day which really kept us from worrying about our fur babies! She also left us a clean house and kept up on the dog items that needed washing. We will definitely call Kathy G again!
What an absolute Doll Tearia is… she did a fantastic job with our babies today… she put the thunder hood and thunder shirt on one of my Goldens during the storm. She was on time and the house was perfect when we got home. She left a lovely note and we will definitely be calling her in the future! Top notch!
Kim is an incredible human, and our first choice with who we will trust with our home and our pets while we are away. She is excellent at giving updates and sending pictures, she is on time, she is kind, trustworthy, and she clearly loves her work. Thank you, Kim!
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.
Second time I’ve had Kayli watch Tully and she did great as always!! I’m always at ease when I’m out of town and she’s in her care. It’s also great that she watches her at my house where Tully is comfortable. Would recommend to anyone. And will clearly reach out for the next trip I book.
This was my first time using Rover for overnight and housesitting services and I can honestly say, I feel like we got lucky. Alex was incredible. Communicated with us daily, and even made an impromptu visit to the vet to pick up meds. Happy to have her as part of our pack. -Abby, Kratos and Rusko 😊
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 $45
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 $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 Aug 2025, there are 294 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 13 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.
Connect anywhere with the Rover app
