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

“Sarah always does a great job. She is very respectful and courteous when house sitting and is good at communicating. Most importantly, my elderly (and very picky cat who doesn’t like people) adores Sarah.”


“Pamela was wonderful with our three dogs! She was very responsive and friendly and they enjoyed their time with her. Pam was also flexible enough to accommodate a last minute booking change due to illness. We enjoyed meeting her and will be booking her again!”


“We were so grateful to Emily for being available on short notice and on Christmas night, no less! While we were staying with family over the holidays, Dudley was less than happy to be left with a dog sitter in a home he was unfamiliar with. Emily was great in understanding his behavior and gave him time and space to adjust to our being gone. She sent us pictures and let us know that while not happy, he was doing fine. We so appreciated Emily's sweet nature in dealing with our sulky boy. We would absolutely recommend her to anyone needing a sitter and would use her again next time we're in town!”


“We were so happy to find Hannah to watch our fur baby! He is fearful of new people and staying away from home and Hannah took great care of him. We don’t like to leave him for extended periods alone at home and she was more than willing to accommodate our request. She was also patient with us and our check ins.”


About: I’m dedicated to giving your furry friends the best care and companionship they deserve! Although my current living arrangement doesn’t allow me to have a dog, I’m the fun ‘puppy aunt’ who loves spending time with my friends’ dogs. I’m passionate about playtime, hikes, and long walks, and I’m always eager to shower dogs with love and attention. My ability to connect with dogs and keep them active and engaged sets me apart, and I bring a warm, caring energy that makes them feel right at home. I have three cats. Through more than one decade of cat care experience, I have learned the importance of play, food routines, and litter box cleanliness. Most of my friends have cats as well; I’m familiar with the process of gently introducing myself to a new feline friend and providing care while their pet-parent is on vacation. I’m typically available all day on Sunday, Monday, and Tuesday. If you require pet care Wednesday-Saturday, please message me for my availability. I am excited to take care of your beloved furry friend, ensuring they receive plenty of attention, exercise, and care. I pride myself on creating a routine that helps pets feel comfortable, secure, and loved while their owners are away When caring for pets in the owner’s home, I prioritize creating a comfortable and familiar environment for them. I follow the pet’s usual routine, including feeding, walking, playtime, and providing companionship. I ensure their safety and well-being by maintaining a clean and secure space, and I give them plenty of affection and attention. I also keep the owner updated with regular check-ins and photos to ensure peace of mind while they’re away.

About: I have had dogs and cats as pets throughout most of my life. At a young age it was instilled into my heart that pets are family members. And that is a sentiment I have stuck with my entire life. I have also kept a few fish tanks, too! I work full-time but I am done fairly early, so I will be available Mondays through Thursdays from around 3pm until 830pm, (I could do an overnight stay during the weekdays too if it isn't too far from my home base). Fridays after work through Sundays I am available anytime! I'm down-to-earth and believe communication is key. The best way for me to provide the care, love, and attention your pet requires is for us humans to have open communication. If there is something you request, and I wouldn't be able to provide, I will be up front and let you know. You'd be able to see through me if I said doing Rover is not for the money, HOWEVER, that is not the sole reason! The safety and care of your pet is by far THE most important thing. I believe we can achieve pet-happiness by each of us being up front and honest.

“Hannah took wonderful care of my chihuahua and cat! My chihuahua is very particular about people and he absolutely adores her! She is my go to sitter. Thank you for making my fur babies feel loved and at home while we were away. 😊”


“Shandy is an amazing woman. She sent us photos every few hours of the dogs, and took amazing care of our cats and the houses. She truly is someone I would trust with everything!!!!! This was our first time leaving our dogs with someone that wasn’t immediate family. Shandy is now always apart of our family and always welcomed back. She is AMAZING!”


“Blane was great! Was able to help me in a pinch and watch my pets on short notice. She’s great at communicating, providing updates and paying attention to details. I felt like my pets were in great hands. Highly recommend!!”


About: I have been an animal lover since I was born! I grew up on a farm that included all farm animals; mainly horses, dogs, and cats. I’ve had many years of experience with training, and proper pet care! I currently work from home and I have plenty of time throughout the day for pet sitting! I’m available 24/7 I enjoy walks, and nature so I spend a lot of time outside. I have a large fenced yard, fit for animals. We have a loving friendly 7 year old hound dog named Copper. We live in a safe quiet neighborhood close to trails and parks.

“Our dogs enjoyed their time with Christopher! He has a calm and relaxing presence with our anxious pup. Great communication allowed us to relax and enjoy our time away. Will be requesting Christopher again!”


About: Barking up the wrong tree? I can help! Dogs are amazing! I spend a lot of time working with k9s! Training, fostering, and medical care. There’s no job to big or small with it comes to pooches! Me and My Dog: I have one dog of my own, Chandler! Chandler is a very special boy! A retired police k9 who now spends his days protecting me and my home. But don’t let that intimidate you! Chandler is a certified sweet boy at heart. He loves all dogs, cats, people, big, small, old, or young. He has nothing but love to give! We spend everyday together, he is truly my best friend! I am home all day everyday, besides the occasional trip to the store or running errands. So I have endless time to look after your furry friend! I’m available for bookings throughout the week and weekends! My home: I live in a spacious apartment with one friendly dog and an outdoor kitty! I have a fenced area for potty breaks and play time! Pets are allowed on the furniture and bed in my home!🙂 if your dog is crate trained please let me know so I can see if I have a sizeable crate to provide for your pooch during their stay! Your home: A lot of us love being in the comfort of our own home! And so do some dogs! I provide overnight housesitting, and drop ins for the homebodies! Please provide me with a thorough list of instructions and your wish will be my command!

About: Hey guys! I have been fostering, rescuing and babysitting for about 8 years now but have put a pause on the fostering and rescuing for now because I’m new here! But I was raised in Miami I’ve just been going all around but now I’m in Roseburg! I definitely have seen a lot in my years of rescuing and fostering cats mostly. I have had a few pup rescues as well . But I do have 1 Pitty “aggressive breed” of my own that acts like a huge teddy bear that I love dearly which is when the babysitting came into play because she loves meeting new animals(and so do I). I am an animal lover all around and will babysit your raccoon if you had one!Seriously as long as it’s okay with my fur babies lol. I am here for you and your babies not the money I do know it’s hard trusting people with your animals I have had a few crazy experiences myself so I will do anything to make you and your babies feel at ease. I can’t forget about my cats,I have 1 long hair cat myself so all animals that board with me must be respectful of them so we’re all having a good time and no one is stressed. And one rescue cat at the moment. My trio are a pretty chill bunch. I once babysat a “friendly dog” who tried lunging at my dog numerous times so that dog had to be picked up early unfortunately so now meet ups are a REQUIREMENT. Just for the safety of all animals because your baby will basically be mine for the time being and they will get all the love I have to give! I can’t wait to hear back from you guys. I am also a chef soooo if your dog doesn’t have a sensitive tummy I will offer them homemade dinners and treats with your permission of course and I’d tell you the ingredients incase of allergies. I only crate pups when I’m away if they aren’t house broken or in a gated area will be set up for them while I’m away! (Like if I go on a quick grocery run), I personally don’t have a preference so whatever you feel is best let me know. But other then that they are free to do as they feel just like the rest of the animals. BE AWARE they will be spoiled. Right now my schedule is pretty open since I’ve just moved out here. I only do Instacart for right now but looking to do Rover again. I do know some pups are runners and etc but I won’t let anything happen to your babies. Again I’m a very crazy pet mom so I’m strict about them and will give ur animals the same respect.

About: I grew up on a farm taking care of a plethora of different animals! My specialty animals though are Dogs, Cats, Rabbits, Chickens, Ducks, and Fish. I'm always open to learning how to care for other animals that I've never done before too! I look forward to possibly watching your fur babies! Or not fur babies, you get the idea 😂 I work a part time job as a Barista so my availability is usually open around that. Weekends are sometimes more open it just depends on if they need more help at work. I'm a clean, non smoking, responsible adult that would take care of your animals like they were my own! If you have any other questions feel free to ask me!!!

About: For the past seven years I have been walking and caring for a dog in my community. I do have experience with elderly dog, and animals with special needs. I currently work a full-time job, but I’m free most weekends, evenings, and holidays to care for your fur babies. Of course if you have any questions regarding dates or times, just let me know. Of course whatever the client is looking for or know is best for their pet is what I will do. Safety is my number one priority with your family member.

“Breezy was just fabulous took care of my dogs like a they were hers. Was very comfortable that my dogs were in good hands.kept me in touch daily with pictures. Will definitely book breezy again. Thanks breezy for taking care of my dogs.”


About: I absolutely love dogs ! They truly are man’s best friend till the end. I have two dogs of my own , whom I love very much ! I have experience in dog sitting as well as dog walking and I am passionate about providing good care and excited to meet new pups! I fit pet care into my day/week routine because I have two dogs of my own. One is a pit bull and another is a boarder collie so to say they need care is an understatement. They have the upmost energy. I will play with them and wear them out so they get a good nights sleep. With that being said we walk, hike, run, go to the beach, play fetch , etc. as much as we can. I treat my puppies very kindly , if not they’re quite spoiled. 😉 I care very deeply about animals and I aim to help when I can !

About: I have owned a dog and 2 cats for a year now. I have always been around animals growing up. I love taking dogs on walks and playing with furry friends. I’m currently working part time so I have some time to spare. Due to this, my work schedule isn’t always the same each month. But I would love to make some time to help take care of some cute doggies and cats! I have taken care of different kinds of dogs. I rescued a dog from the shelter so I have experience with taking care of animals that can be a bit more difficult. I am willing to clean up messes. I am very patient with animals and I will give them lots of love:)

About: (TWO PEOPLE USING ACCOUNT ME AND MY BF) We both been taking care of our own animals and family members since the age of 9, I love animals with a passion and I will spoil them with affection care and maybe a few treats <3 My pet care has seamlessly become an integral part of my daily routine since childhood. As a pet enthusiast, I dedicate ample time and attention to nurture and care for our furry companions. Each morning, I wake up eager to tend to their needs, starting with feeding and providing fresh water. Throughout the day, I incorporate playtime and interactive sessions to keep them mentally and physically stimulated. During midday lulls, I set aside moments to engage in bonding activities, ensuring they feel loved and cherished. Evenings are dedicated to additional play, grooming, and relaxation, allowing our pets to unwind. By creating a structured routine, I maintain consistency in their care, which in turn fosters a strong and trusting relationship with our beloved pets. Without the confines of a job, I cherish the privilege to spend quality time with our furry friends, providing them with all the care and attention they deserve. Morning: - 7:00 AM: Breakfast time with fresh water - 7:30 AM: Independent playtime with toys Midday: - 12:00 PM: Short play session or interactive toy time Afternoon: - 3:00 PM: Nap time or lounging in a sunny spot Evening: - 6:00 PM: Dinner time with fresh water - 6:30 PM: Interactive play session or grooming Night: - 9:00 PM: Evening playtime or interactive toys - 10:00 PM: Calm and relaxing environment before bedtime
Loving house sitters in your neighborhood
Search Results


1. Sarah J.

“Sarah always does a great job. She is very respectful and courteous when house sitting and is good at communicating. Most importantly, my elderly (and very picky cat who doesn’t like people) adores Sarah.”


2. Pamela M.

“Pamela was wonderful with our three dogs! She was very responsive and friendly and they enjoyed their time with her. Pam was also flexible enough to accommodate a last minute booking change due to illness. We enjoyed meeting her and will be booking her again!”


3. Emily F.

“We were so grateful to Emily for being available on short notice and on Christmas night, no less! While we were staying with family over the holidays, Dudley was less than happy to be left with a dog sitter in a home he was unfamiliar with. Emily was great in understanding his behavior and gave him time and space to adjust to our being gone. She sent us pictures and let us know that while not happy, he was doing fine. We so appreciated Emily's sweet nature in dealing with our sulky boy. We would absolutely recommend her to anyone needing a sitter and would use her again next time we're in town!”


4. Hannah C.

“We were so happy to find Hannah to watch our fur baby! He is fearful of new people and staying away from home and Hannah took great care of him. We don’t like to leave him for extended periods alone at home and she was more than willing to accommodate our request. She was also patient with us and our check ins.”


5. Amelia P.
“Amelia is absolutely wonderful with my cat. She’s not only reliable but genuinely cares about his well-being. She takes the time to play with him, make sure he’s comfortable, and even sends me updates while I’m away. It’s clear she loves animals, and I feel completely at ease leaving my cat in her care. I can’t recommend her enough!”


6. Jenny K.
“Jenny is an amazing caregiver to her pets and any other pets I've seen her encounter. Growing up we had cats and later a dog. Jenny showered them with as much love as she had. She went on to own many more pets in the future, and they were always excellently taken care of.”


7. Hannah H.

“Hannah took wonderful care of my chihuahua and cat! My chihuahua is very particular about people and he absolutely adores her! She is my go to sitter. Thank you for making my fur babies feel loved and at home while we were away. 😊”


8. SHANDY D.

“Shandy is an amazing woman. She sent us photos every few hours of the dogs, and took amazing care of our cats and the houses. She truly is someone I would trust with everything!!!!! This was our first time leaving our dogs with someone that wasn’t immediate family. Shandy is now always apart of our family and always welcomed back. She is AMAZING!”


9. Blane I.

“Blane was great! Was able to help me in a pinch and watch my pets on short notice. She’s great at communicating, providing updates and paying attention to details. I felt like my pets were in great hands. Highly recommend!!”


10. Danielle H.
“Danielle is such an amazing lady ,she took wonderful care of our pets and our yard.. She treats them as her own fur kids , which makes our hearts happy and at ease when traveling, knowing she has it covered... Highly recommend and definitely we use her always..”


11. Christopher C.

“Our dogs enjoyed their time with Christopher! He has a calm and relaxing presence with our anxious pup. Great communication allowed us to relax and enjoy our time away. Will be requesting Christopher again!”


12. Jolene B.
About: Barking up the wrong tree? I can help! Dogs are amazing! I spend a lot of time working with k9s! Training, fostering, and medical care. There’s no job to big or small with it comes to pooches! Me and My Dog: I have one dog of my own, Chandler! Chandler is a very special boy! A retired police k9 who now spends his days protecting me and my home. But don’t let that intimidate you! Chandler is a certified sweet boy at heart. He loves all dogs, cats, people, big, small, old, or young. He has nothing but love to give! We spend everyday together, he is truly my best friend! I am home all day everyday, besides the occasional trip to the store or running errands. So I have endless time to look after your furry friend! I’m available for bookings throughout the week and weekends! My home: I live in a spacious apartment with one friendly dog and an outdoor kitty! I have a fenced area for potty breaks and play time! Pets are allowed on the furniture and bed in my home!🙂 if your dog is crate trained please let me know so I can see if I have a sizeable crate to provide for your pooch during their stay! Your home: A lot of us love being in the comfort of our own home! And so do some dogs! I provide overnight housesitting, and drop ins for the homebodies! Please provide me with a thorough list of instructions and your wish will be my command!


13. Sabrina D.
About: Hey guys! I have been fostering, rescuing and babysitting for about 8 years now but have put a pause on the fostering and rescuing for now because I’m new here! But I was raised in Miami I’ve just been going all around but now I’m in Roseburg! I definitely have seen a lot in my years of rescuing and fostering cats mostly. I have had a few pup rescues as well . But I do have 1 Pitty “aggressive breed” of my own that acts like a huge teddy bear that I love dearly which is when the babysitting came into play because she loves meeting new animals(and so do I). I am an animal lover all around and will babysit your raccoon if you had one!Seriously as long as it’s okay with my fur babies lol. I am here for you and your babies not the money I do know it’s hard trusting people with your animals I have had a few crazy experiences myself so I will do anything to make you and your babies feel at ease. I can’t forget about my cats,I have 1 long hair cat myself so all animals that board with me must be respectful of them so we’re all having a good time and no one is stressed. And one rescue cat at the moment. My trio are a pretty chill bunch. I once babysat a “friendly dog” who tried lunging at my dog numerous times so that dog had to be picked up early unfortunately so now meet ups are a REQUIREMENT. Just for the safety of all animals because your baby will basically be mine for the time being and they will get all the love I have to give! I can’t wait to hear back from you guys. I am also a chef soooo if your dog doesn’t have a sensitive tummy I will offer them homemade dinners and treats with your permission of course and I’d tell you the ingredients incase of allergies. I only crate pups when I’m away if they aren’t house broken or in a gated area will be set up for them while I’m away! (Like if I go on a quick grocery run), I personally don’t have a preference so whatever you feel is best let me know. But other then that they are free to do as they feel just like the rest of the animals. BE AWARE they will be spoiled. Right now my schedule is pretty open since I’ve just moved out here. I only do Instacart for right now but looking to do Rover again. I do know some pups are runners and etc but I won’t let anything happen to your babies. Again I’m a very crazy pet mom so I’m strict about them and will give ur animals the same respect.


14. Mickayla F.
About: I grew up on a farm taking care of a plethora of different animals! My specialty animals though are Dogs, Cats, Rabbits, Chickens, Ducks, and Fish. I'm always open to learning how to care for other animals that I've never done before too! I look forward to possibly watching your fur babies! Or not fur babies, you get the idea 😂 I work a part time job as a Barista so my availability is usually open around that. Weekends are sometimes more open it just depends on if they need more help at work. I'm a clean, non smoking, responsible adult that would take care of your animals like they were my own! If you have any other questions feel free to ask me!!!


15. LaShea R.
About: For the past seven years I have been walking and caring for a dog in my community. I do have experience with elderly dog, and animals with special needs. I currently work a full-time job, but I’m free most weekends, evenings, and holidays to care for your fur babies. Of course if you have any questions regarding dates or times, just let me know. Of course whatever the client is looking for or know is best for their pet is what I will do. Safety is my number one priority with your family member.


16. Breezy K.

“Breezy was just fabulous took care of my dogs like a they were hers. Was very comfortable that my dogs were in good hands.kept me in touch daily with pictures. Will definitely book breezy again. Thanks breezy for taking care of my dogs.”


17. Jewlia C.
About: I absolutely love dogs ! They truly are man’s best friend till the end. I have two dogs of my own , whom I love very much ! I have experience in dog sitting as well as dog walking and I am passionate about providing good care and excited to meet new pups! I fit pet care into my day/week routine because I have two dogs of my own. One is a pit bull and another is a boarder collie so to say they need care is an understatement. They have the upmost energy. I will play with them and wear them out so they get a good nights sleep. With that being said we walk, hike, run, go to the beach, play fetch , etc. as much as we can. I treat my puppies very kindly , if not they’re quite spoiled. 😉 I care very deeply about animals and I aim to help when I can !


18. Elizabet S.
“Elizabeth has been over to watch our 2 dogs many times and they absolutely love her, including our grouchy Beagle who doesn’t get alone with most people. She has shown great compassion for all animals that I’ve seen her with and has a dog of her own that she treats like family. She is patient and understanding to our dogs even when they are not at their best behavior. I recommend Elizabeth to anyone who is wanting their dogs or cats taken good care of. She is also capable of walking with them with no issues.”


19. Qianna O.
About: (TWO PEOPLE USING ACCOUNT ME AND MY BF) We both been taking care of our own animals and family members since the age of 9, I love animals with a passion and I will spoil them with affection care and maybe a few treats <3 My pet care has seamlessly become an integral part of my daily routine since childhood. As a pet enthusiast, I dedicate ample time and attention to nurture and care for our furry companions. Each morning, I wake up eager to tend to their needs, starting with feeding and providing fresh water. Throughout the day, I incorporate playtime and interactive sessions to keep them mentally and physically stimulated. During midday lulls, I set aside moments to engage in bonding activities, ensuring they feel loved and cherished. Evenings are dedicated to additional play, grooming, and relaxation, allowing our pets to unwind. By creating a structured routine, I maintain consistency in their care, which in turn fosters a strong and trusting relationship with our beloved pets. Without the confines of a job, I cherish the privilege to spend quality time with our furry friends, providing them with all the care and attention they deserve. Morning: - 7:00 AM: Breakfast time with fresh water - 7:30 AM: Independent playtime with toys Midday: - 12:00 PM: Short play session or interactive toy time Afternoon: - 3:00 PM: Nap time or lounging in a sunny spot Evening: - 6:00 PM: Dinner time with fresh water - 6:30 PM: Interactive play session or grooming Night: - 9:00 PM: Evening playtime or interactive toys - 10:00 PM: Calm and relaxing environment before bedtime
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. 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 Apr 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 Apr 2025, there are 33 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, 95% of Winchester house sitters respond in under an hour.
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.
