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.
“We had an amazing experience with Farrin as our pet sitter for our dog, Taco. She took excellent care of him overnight, making sure to give him plenty of playtime and cuddles while we were away. Farrin was respectful of our home, leaving everything clean and tidy, which we really appreciated. She even came by for a meet and greet before the booking, giving us peace of mind. We would absolutely book with Farrin again in a heartbeat! Highly recommend her!”
“Madison was wonderful! Our dogs were well loved and cared for! She sent regular updates and photos of our dogs- which we loved and could see how happy they were. Our house was well taken care of too! Will be booking her again in the future!”
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 have had dogs, cats, birds, horses, and ducks growing up. I love animals of all kinds and any furry friend is always welcome in my home! I am not currently working and I am a stay at home mother so I am basically always free. My son is two and loves animals! We have a ton of toys for your little guy to play with. I also have experience in dog training so we might practice some new tricks! We take frequent walks to the park as well.
“Olga and Stepan took great care of my two dogs while I was away. They sent me pictures, administered meds, took them for walks, and gave them plenty of affection. One of them was home with the dogs at all times which I am sure they enjoyed since I cannot work from home. I highly recommend them and will definitely request them again.”
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: I have hands on experience caring for animals through my work at Alpha Pet Resort since July 2023. Where I feed animals, monitor behavior, clean kennels, and just make sure animals are comfortable and safe. I also have experience volunteering and local animal shelters. I am responsible, patient, and passionate about providing animals with the care and attention they deserve. I am currently available most days and have a flexible availability. Since I am currently looking for part time work hours may vary, but I am generally available most times and am happy to coordinate with pet owners to find a schedule that works for both of us. When caring for pets in their home, I would make sure to follow the owners instructions and maintain their normal routine as closely as possible. I would care for each pets individual needs. I would also be respectful of the clients home by keeping it clean and secure.
“Makalah is our first pet sitter from Rover. We hired her for house sitting so that she could care for our dog and cat in the comfort of their own home. We have had friends and family take care of the pets, but we’ve never had someone come spend the night. Makalah did an amazing job with both our pets. She bonded instantly with our cat and as she said, He’s my bestie! Our dog is 13 years old and requires more care, as he takes seizure medication three times a day. Makalah took on this responsibility and she made sure she let me know when she gave him his meds. Makalah’s communication with me throughout the day and night was great. She also sent pictures of both pets along with an update on how things were going. I am so glad I decided to take a chance with Rover and with Makalah. We will definitely be calling in her to care for our pets again.”
About: I'm good with all kinds of pets and love giving special attention to your loved ones. I have trained my own service dog, and have 4 other well behaved animals in my home. Let me help you with all your pet needs. I even have experience with animals with special needs. Currently, I'm a stay at home wife and have pretty much unlimited availability to take care of your pets. I'm willing to watch your pet in your home or mine. If we were to need to watch them at my house I have 1.5 acres for them to run and play. I have a 2,000 square foot home with plenty of space for activities as well. In your home I will follow the rules set by you and your family with your pet and will definitely spoil them as much as I can with daily pictures to show how they are doing with any pertinent details you would need/like to know about their day.
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!
“Scott and Sarah were fantastic. I really appreciated their level of communication, care, state in which they left my home. They pay attention to the details. Every picture I received of my dogs, it looked like they were smiling ear to ear and have the best days. So cute.”
About: I have taken care of multiple animals throughout my life, mainly elder neighbors who cannot fully take care of their animals because of scheduling conflicts. I prefer overnight visits and stays just to ensure no schedules are disrupted. I currently attend UVA full-time as a Master's Student, and work Saturday nights at a restaurant in Cville. But I always make time for the animals in my life! I have a fenced-in yard, I walk dogs either for short 15/20 minutes, or a longer (5 miles) depending on a breed's needs and requirements. Otherwise, we can lounge and play with toys together.
“Deborah was absolutely wonderful when she house sat for us while we were out of town! Our Great Dane loved her and our house was in better shape than when we left! 10/10 recommend and will be using her again in the future!!”
About: I have 3 years of professional experience working in the animal industry and currently work at a veterinary hospital, where I provide hands-on care to a variety of pets every day. My experience has given me a strong understanding of animal behavior, health, safety, and the individual needs of different pets. I’m comfortable caring for dogs and cats of different ages, sizes, breeds, and temperaments, including pets who may require extra patience, medication, or specialized care. Working in a veterinary environment has also taught me how to recognize changes in behavior or health and respond appropriately when a pet may not be feeling their best. When caring for your pets, my priority is to make them feel safe, comfortable, and loved while maintaining their normal routines as closely as possible. I understand that every pet is different, and I’m happy to follow detailed instructions regarding feeding, walks, medications, exercise, and other specific needs. You can feel confident knowing that your pets are in the care of someone with professional animal-care experience who genuinely enjoys helping animals and treating every pet as if they were my own. Depending on my schedule I work from 7am - 3pm or 8am - 5pm, before or after my regular job I am free to hang out with your fuzzy guy! I care for pets in my clients’ homes by keeping them comfortable, safe, and as close to their normal routine as possible. I follow each pet’s individual care instructions for feeding, walks, playtime, medications, and any special needs. I also make sure they receive plenty of attention, affection, and enrichment while their owners are away. With 3 years of experience in the animal industry and my current work at a veterinary hospital, I’m comfortable caring for pets with a variety of personalities and needs. I pay close attention to changes in behavior, appetite, energy levels, or other signs that something may be wrong, and I communicate with the owner promptly if I have any concerns. I also treat my clients’ homes with the same respect and care I give their pets, keeping things clean and secure and providing updates so owners can have peace of mind while they’re away.
“Ananda did an amazing job with my little pack! Including my blind, senior girl who needs extra TLC. I never worried about them, as she would check in and send pictures—-which was great as I was out of the country. We will definitely have Ananda visit again on my next trip away from my furkids!”
About: I have been pet-sitting since I was 10 years old. I have always loved animals with my whole heart. My family, friends, and neighbors have trusted me to take care of, feed, walk, and bathe their pets while they are away. I am especially praised for the amount of time I spend hanging out with the pets. I like I hang out with them as much as I can and get in all the cuddles so they know they are safe with me and feel all of my love while their owners are away! This works with my schedules perfectly! I typically work 8 hour days, so mid day check ins, and evening care work perfectly for me since I am available to stay at the pets house with them! I spend a lot of time with the animals when I am there. I always allow cuddles and honestly it is my favorite part of the job. Coming back to a pet that is excited to see you is the best feeling in the world. I make sure the dogs get plenty of time outside, and long walks if the weather permits. I love playing with the animals. Cats or dogs! I love seeing the pets be comfortable with me and building that bond between the animals and myself!
“We loved working with Anastasia! She stayed at our home with our dog for a week. She was a perfect and polite houseguest and took such good care of our dog. She sent tons of pictures, videos, and updates. We felt so comfortable and relieved on our vacation leaving our dog and our home in Anastasia’s care. We fully recommend working with her!”
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 4 repeat house sitting clients
FAQs for House Sitting - Winston
Frequently asked questions about Rover
As of November 2026, there are 535 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.
Tip: 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 Rover Guarantee, 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 Rover's Trust & Safety page.
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 Meet & Greet.
sitters on Rover set their own cancellation policy, 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.
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