House Sitting Winston
Find a loving house sitter to watch over your pets and your home.

Winston, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

About: Hello, I have been taking care of a wide range of animals since I was 15. I’ve had 5 ferrets, guinea pigs, cats and dogs my whole life. I have a Staffordshire terrier, an American bully, and a black lab/ leopard catahoula mix. I am used to having a heavy dog on the opposite end of the leash and I am well experienced in animal body language to keep your baby and myself safe. I am an independent contractor who does Rover, Spark, DoorDash and a couple other side gigs. I have worked a 9-5 and it was incredibly difficult following a schedule someone else made for me while trying to manage my kids school and sports schedule's. Since becoming an independent contractor I have gained great relationships with residents of Culpeper and Rappahannock county and more time with my kids. These side gigs help provide me a way to bring in income, socalize, work easily with my kids school and sport schedules and give me the flexibility to rest when my autoimmune disease flares up. I will make sure any and all instructions are followed correctly to ensure adequate and safe service. Plus a few head rubs before I left.

“Ronda was not only efficient and responsive, sharing twice-daily feedback about the care and feeding of our two kitties, but she was also able to establish an affectionate bond with them during our 16-day absence. We are pleased to give Ronda 5 stars and would highly recommend her.”

About: Love your pet but short on time? I've got you covered. I'm a passionate pet professional dedicated to making your life easier through two key services: 1. Active Care & Cuddles: Book me on Rover for reliable dog walking, sitting, and drop-in visits. I'll make sure your pet gets the exercise, attention, and care they need. 2. The Dirty Work, Done: Hate cleaning the yard? I own and operate Sure Scoops to handle that for you. Get a pristine, sanitized yard without lifting a finger. My dream is to support loving pet homes by handling the challenges—from daily exercise to daily mess. Let me help you focus on the love, not the logistics! Find me on Rover for walks & sits! Message me directly for Sure Scoops yard clean-up! I’m currently working part-time from home, so I’ll have plenty of time to play with and supervise your pups! I’m available for boarding on weekends, and throughout the week for daycare and flexible overnight stays, ensuring constant care and attention. I provide care in a secure, pet-proofed home with a fully fenced 500+ sq ft yard. My two friendly dogs offer excellent companionship. I am experienced in administering medication, following specific dietary routines, and can easily crate your dog if needed for their comfort and safety.
About: I’m currently doing a certificate online to become a pet vet assistant,I also like baking in free time and spend time friends ,and I mainly love dogs and cats since growing up I currently don’t have job at the moment and I wanted to get some experience being around pets more often so I’m available most of the time so I thought why try this I care for any pet that I run into even if I don’t know them well,for example on one of my walks I helped a woman catch there dog that got off there leash
About: Hi! I’m an experienced animal care professional with 15 years of experience as a zookeeper, and animals have always been a huge part of my life. Throughout my career, I’ve had the privilege of caring for and working with all kinds of species, giving me a deep understanding of animal behavior, individual needs, and the importance of patience, compassion, and trust. Whether your pet is playful and energetic, shy and nervous, senior, or simply loves some extra attention, I’m comfortable meeting them where they are and providing care tailored to their personality and routine. I know how important it is to feel confident that your pets are safe, happy, and well cared for while you’re away. I treat every animal in my care as an individual and take pride in providing dependable, attentive, and loving care. I’d love the opportunity to get to know your pets and give them the same care and attention I would want for my own! I work from home with a flexible part-time schedule, giving me plenty of time and availability to provide attentive care and drop-in visits for your pets. Since I have pets of my own, I primarily focus on drop-in visits. However, I’m always happy to discuss other options to find the best arrangement for you and your pets.
“Such a nice young Lady. Shes like a dog whisperer, they loved her instantly! My dogs dont get that excited when I come home! Top notch! I would give her ten stars if I could. Madison went above and beyond!”

About: I adopted my first dog, Ollie, when I was 18 years old. Shortly after I discovered he was suffering from kidney failure and epilepsy. This resulted in frequent vet visits and daily medications, and I'm comfortable administering medication to your pets. Now, I have three cats that I've had for almost five years, living their best lives. I love my pets and I'm looking forward to giving your best friends the same level of love and care. I work full-time. I'm available after 2pm on most days - I try to keep my availability on my profile accurate but due to the nature of my job I may have more or less availability than what is listed. Please don't hesitate to reach out and ask! Daily care routine starts in the morning with food, medication, and cleaning litter boxes. We play at their request and make sure they have access to all their toys.
“This is the 1st time in 8+ years of having our dogs, we used Rover while going on a 4 day vacation. We found Toni literally 1 day before our travel and she was a great match for our pups. She has been very professional and kept us updated regularly with both photos and also text messages. I would have her house sit again if we need to go on vacation and I would totally recommend her for anyone”


About: I’ve taken care of dogs of every kind — from playful puppies to gentle seniors, and everything in between. I am the go to dog sitter for all my family and friends! Pet care fits naturally into my daily routine because I’m home most of the time and able to give pets plenty of attention, care, and supervision throughout the day. I treat every pet like part of the family! I make sure they feel safe, comfortable, and loved while in my care. I provide dependable care and regular updates!
About: Welcome! With 15+ years of experience and a genuine love for dogs, I provide a calm, safe, home-away-from-home experience for your pup. I work from home, so when your dog stays with me, they’re never left alone—they have companionship, supervision, and care 24/7. I also only accept one family’s pets at a time, so your dog receives my full attention without the stress of a crowded environment. My fully fenced one-acre yard offers plenty of space to run, play, and explore safely, while inside they’re treated like part of the family. My goal is simple: to give you complete peace of mind knowing your pet is safe, loved, and cared for as if they were my own. I look forward to welcoming you and your furry family member! Pet care fits naturally into my daily routine because I work from home full-time, which allows me to be fully present and attentive throughout the day. My dogs are part of my life, not just my schedule — and the same goes for any pet I care for. I build my day around walks, enrichment activities, playtime, and quiet moments, making sure each dog gets the stimulation and comfort they need. Rover isn't just a side gig for me — it’s something I genuinely care about. I love being able to share my time and home with other pets, giving them the same level of love and attention I give to my own. In my home, your pet will be treated like one of the family. I have a fully fenced one-acre yard for safe, supervised outdoor play, and two small, friendly dogs to provide companionship if your pup enjoys socializing. I ensure 24/7 access to fresh drinking water, regular bathroom breaks, and a calm, cozy indoor environment where your dog can relax freely — crated only if you prefer. I follow your care instructions closely, including administering any medications as prescribed. Whether it’s maintaining their feeding schedule, providing playtime, or offering extra snuggles, I make sure your pet feels safe, comfortable, and loved — just like they would at home.
About: Hey! I'm super passionate about animals and have tons of experience caring for them. I've grown up with pets my whole life, from dogs and cats to hamsters and fish, so I'm comfortable with all kinds of animals. I'm responsible, reliable, and always put the needs of the pets first, making sure they're safe, happy, and well-cared for while you're away! I am available to provide care for any furry friend at any moment. No matter they need, I’m always available to treat your animal, as if they were my own. I treat pets just like family. they are family to me and deserve to be treated with passion and integrity. Their emotions are stronger than the average person.
“Deborah was Great! She took excellent care on my 2 fur babies! She was very attentive and loving. I loved the photos and updates during the days, kept my mind at ease. When we returned, they were happy and well fed. I can see that Deborah went out of her way to make sure that they ate, cause my pups never eat when we leave them. She left the house meticulous, I will definitely be booking Deborah for my future trips!! ?. Thank you Deborah”

About: I provide pet care with a genuine focus on safety, structure, compassion and comfort. I'm patient, attentive, and committed to making every pet feel secure, loved, and understood. I have experience with puppies, but senior pups have my heart. One thing my clients like is how connected they feel while they're away. I take lots of photos and videos throughout the day and send daily updates so you always know how your pet is doing. Your pet's happiness and well-being are my priority, and I make sure you feel just as supported as they do. My goal is to make them feel at home and cared for and return back to you happy, relaxed and well cared for. I recently left my position as a General Manager to pursue my love for animals full-time, which means pet care is now the center of my daily routine. I structure my days around the pet's I'm caring for, making sure they get consistent walks, playtime, feedings and lots of snuggles. I am able to be flexible, responsive, and fully present with every pet in my care. Your pet will always have my time, my patience and my full commitment. My care is always tailored to each family’s needs and each pet’s personality. When I’m caring for pets in your home, I follow your established routines—feeding schedules, walk times, house rules, and any specific training or comfort needs. If you have a fenced-in yard, I ensure your pet gets safe outdoor time. If leash walking is required, I provide structured, attentive walks based on your pet’s energy level. When pets stay in my home, they’re welcomed into a calm, country setting with a large, open yard. While I don’t have a fenced-in backyard, safety is always my priority. Until I fully know and trust your pet’s recall, behavior, and comfort level, all outdoor time will be done on leash. Once I understand their temperament and you are comfortable, we can adjust as appropriate. No matter the environment, my goal is to make every pet feel safe, secure, and truly cared for whether I’m in your home or mine.
“Sophia was an amazing Rover! She kept us updated the whole time and seriously spoiled Roxie while we were gone! Is was so nice knowing our dog was in good hands the whole time we were gone:)”

About: Please take a moment to read my full description 🐾💛. It’s very important to me that you do, as everything I include here is designed for the benefit of everyone involved —your pet, myself as their caregiver, and you as their loving parents, because I know your furry friend is truly part of your family and deserves the best care. You may find that what I’ve written here answers several of your questions, especially if this is your first time leaving your pet in someone else’s care. Here you’ll find all the details about boarding and daycare, including my routine, flexibility, safety measures, and how I care for each pet’s needs. If you have any questions or additional concerns, please don’t hesitate to contact me. I’ll be happy to answer everything you need so you can feel completely comfortable and at ease before booking. 🐾✨ ⸻ Hi! I’m Romely, a lifelong animal lover currently living in Virginia. I’m bilingual (English & Spanish), so I can communicate comfortably in both languages —making it easier for you to feel understood and confident when we talk about your furry family member. 💬🐾 I began my journey as a rescuer and volunteer in animal shelters in Puerto Rico, caring for dogs and cats in delicate conditions and staying by their side until they found their forever homes. That experience taught me empathy, patience, and what it truly means to care from the heart. After moving to Virginia, I continued volunteering at local shelters, gaining even more experience with pets of all ages, sizes, and special needs. Caring for animals remains the heart of my daily life. At home, your pet will meet Athenas, my sweet, calm, and friendly dog who loves making new friends —both dogs and cats. I like to provide a balanced routine, with fun walks around our community’s pet park, interactive play, mental stimulation, and cozy relaxation time in a safe, loving environment. During their stay or care, your pet is my priority. I make sure they receive all my attention, love, and supervision so they feel comfortable, happy, and safe at all times. 💛🐾 For me, the most important thing is your pet’s safety and your peace of mind, knowing your furry friend is in good hands. I like to maintain constant communication with pet parents and share multiple updates throughout the day, whether it’s photos, videos, or messages showing how your pet’s day is going. 📸🐾 I never call unless it’s an emergency, but I genuinely enjoy keeping you updated because I know how important it is to feel connected and reassured. If you prefer a different communication style (for example, fewer updates or only once a day), just let me know —I’ll gladly adapt to your preferences. 💕 I’m trained in Pet CPR and First Aid, and I’m comfortable administering oral medications when needed. I completely understand that leaving your pet in someone else’s care can be hard —for both you and your furry friend. That’s why I do everything possible to ensure everyone feels comfortable and at peace from the very beginning. We love treating every pet as part of our own family, giving them the same love, respect, and attention we give to our own. ✨ I only host one family at a time to guarantee fully personalized care. For day sitting, I can care for up to two pets per day, always ensuring each one receives the attention, love, and space they deserve. We also love celebrating pets! 🥳 If your furry friend has a special day —like a birthday or adoption anniversary— please let me know. I enjoy hosting small “puppy parties” and making homemade pupcakes, decorating the space to make their stay extra special. 🎂🐾 📸 I also love photographing pets during their stay and sharing some of those joyful moments on Rover or social media, showing happy, everyday activities. If you’d prefer that I don’t post photos of your pet, please just let me know —I’ll fully respect your wishes. 💕 💻 Since I work from home, I’m not available for in-person meet & greets, as I often have meetings or need to be on call, and I wouldn’t be able to give you the full attention you deserve. I also made this decision because most of my apartment is carpeted, and some people prefer not to remove their shoes when entering. In our home, we don’t wear shoes indoors, keeping the environment clean and safe for the pets. At the entrance, we have a paw-cleaning station, where every time the dogs go out or come back in, we wash their paws with dog-safe soap and water before letting them walk freely inside the apartment. I’m happy to share details about the soap I use, and if your pet has any allergies or needs a specific type of shampoo, please let me know so I can use their own product and ensure their comfort and safety. 🧼🐾 It’s also very important to let me know if your dog has any food allergies or follows a strict diet. Sometimes a small piece of fruit, a bit of cheese, or a treat dogs love 🧀🍎 might sneak its way in —and I always want to make sure everything your pet receives is completely safe. 💕🐶 For Drop-Off and Pick-Up, you’re welcome to come right up to my door to say goodbye to your furry friend, or if you prefer, you can sit on the porch for a few minutes to have a calm and loving farewell. The same applies when you come for pick-up —I want both you and your pet to feel relaxed and supported during that transition. 💛🐾 🐾 I’m also very flexible with schedules and family needs. If you live nearby, I can offer free pick-up for your pet. If you’re a bit farther away, I can still help with transportation for a small, low fee, just to cover travel costs. I’m also flexible with drop-off and pick-up times —you can set them through the app, but if something unexpected comes up or you need to adjust, please don’t stress! I completely understand. If your dog is with me for day sitting and something comes up at the last minute where they need to stay overnight, don’t worry —these things happen, and I’ll gladly make sure they’re safe and comfortable for the night. 🌙🐾 And if your booking was last-minute and you didn’t have time to buy food or any items your pet might need for their stay, I can take care of that for you and do the shopping myself to make sure your furry friend has everything they need. 🛒💕 If, for any reason, your pet needs to extend their stay, I can often make exceptions when possible, even if Rover shows no availability. My priority is to keep everything stress-free for both you and your pet. 💕 That said, I’m happy to schedule a 15-minute virtual tour of my home, send videos of the community and the dog park, and meet through a video call before your pet’s stay. This way, you can feel completely comfortable and confident before leaving your furry family member with me. 💕 Thank you so much for considering my services! I can’t wait to meet you and your beloved pet. 🌿🐶 I work from home full-time, so your pet will always have company, attention, and supervision throughout the day. I’m available on weekdays, weekends, and even for last-minute bookings, giving you peace of mind knowing your furry friend is always cared for and never left alone. I live in a safe, pet-friendly community with its own dog park, perfect for daily walks, exercise, and playtime. At home, your pet will meet Athenas, our sweet and friendly dog who loves both dogs and cats. If needed, I can provide crate space or separate areas to make sure every pet feels safe, comfortable, and loved.
The median cost per night for house sitting in Winston is $50
Pet parents share their Rover experiences - Winston
I’m so pleased with Katie, my boys were so well cared for. I received pictures and recaps of their day which put me at ease, as it was the first time I’ve left them. Katie is very professional and I would not hesitate to book with her again…Thank you Rover for such an excellent experience

Katie watched our cat and did some house sitting for several days, and she did an amazing job! She sent picture updates that gave me so much peace of mind, and he was clearly happy, playful, and well cared for. She followed all his routines, kept everything tidy, and was great at communicating. I’d definitely recommend her and would happily book with her again!! 10/10!

Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.
How to book house sitting

1. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Winston
Select a filter and find qualifying sitters offering house sitting.Sitters in Winston average 3 repeat house sitting clients
FAQs for House Sitting - Winston
Frequently asked questions about Rover
As of October 2026, there are 536 sitters on Rover offering House Sitting across Winston. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winston walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winston maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
<b>Tip:</b> Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winston choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the , which provides up to 25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winston. On Rover:
- 92% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 97% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.






