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.
“Terry has been amazing. He's went above and beyond when it came to sitting for Yuki and Koda. I highly recommend his services and we will 100% be returning to him for future sitting needs.”
“Tiffany is just fabulous!!! She stayed at our house for multiple days to care for our pupper. She pamper our fur baby, kept ongoing pictures and updates flowing our way. This gave us confidence that we selected the perfect person to sit for our dog. Great job Tiffany!!!”
“Rachel was caring and patient with our dog. It was our dogs first time with a sitter but Rachel made it a wonderful experience. We’re booking her again and recommend her to watch your pet!”
About: (I Speak English & Spanish) I’ve grown up around dogs my entire life and have years of experience caring for pets belonging to friends and family as well. From walks, feeding, and bathing to bottle-feeding puppies, I truly love and care for pets of all ages. We have a fenced yard where your pup can safely run and play while always being supervised. I’d also love to take your fur baby on walks around our 20-acre property - we can walk down to the barn, explore the land, and enjoy plenty of fresh air and exercise together. I’m currently a student at the University of Kentucky, and I schedule all of my classes on just two days a week, so I’m home most of the time. My husband also works from home, which means your pet will always have company and will never be left alone. During your pet’s stay, I’ll send plenty of pictures and videos so you can feel connected and reassured while you’re away. I’ve also completed dog training classes and would be happy to practice basic commands or even teach your pup a few fun tricks! My schedule is very flexible, so whether you need care planned in advance or last-minute help, I’m here for you and your fur baby. 😃 I’m currently a student at the University of Kentucky and attend classes only twice a week. My husband works from home, so there is always someone at home. Because of that, we’ll have plenty of time and attention to give your pups, making sure they’re well cared for, played with, and loved while they’re with us. I have a fenced in yard, and they will never be without supervision. I have a friendly Golden Retriever to keep you fur baby company as well. I also have crates, so if needed or if you would prefer, the crates are accessible. If you have a pet in heat, and you need to go out for a while, no worries just let me know and I can accommodate to make sure your fur baby has fun and is also kept safe.
About: I’ve had dogs since I was a kid. I’ve cared for friends and families dogs of all sizes and ages. I currently have a female American bully but in the past I’ve had English mastiffs, pit bulls, and a border collie. I enjoy high energy dogs that love to run and play as well as older dogs that just want to play around and be loved on. I’m currently on summer break. I am an athlete at Eastern Kentucky University and have required practices every day but I’m gone no longer than 3 hours per day. I currently live in an apartment with a dog park on site I also have one friendly and very active pup to keep yours company. I will always be outside with the pups they are never out there alone.
About: Dogs have always been a big part of my life, and caring for them is something I truly enjoy. I have experience caring for dogs of different sizes, breeds, and ages. What sets me apart is that I provide a loving family environment where dogs are treated like members of the family. My home is full of attention, affection, playtime, and companionship. I understand that every dog has unique needs, and we take the time to make them feel safe, comfortable, and loved while you’re away. I am comfortable following feeding schedules, administering most basic medications, caring for senior dogs, and helping reinforce routines and good behaviors. My two kids also love dogs and enjoy giving them extra attention and playtime, helping create a warm and welcoming atmosphere for every furry guest. My goal is to give you peace of mind knowing your dog is being cared for in a safe, loving home where they will receive plenty of attention and affection. 🐾 I am currently in nursing school only 2 days a week and my husband works for a healthcare company from home so someone will always be there for your pup. I treat animals as if they are my own children. I will keep them safe and satisfied while you are away so you can have a peace of mind wherever you go.
“Anna was absolutely amazing! She stayed at our house while we were away and went above and beyond every single day. She collected our mail, kept the house tidy, and took incredible care of our dogs. Our collie mix can be highly emotional and needs extra attention, and Anna was truly "the dog whisperer" with her — patient, calm, and clearly attentive to her needs. Both dogs were happy and well cared for the entire time. She sent lots of photos and communicated so well throughout the whole stay — I genuinely didn't worry once, which never happens when we travel! That alone speaks volumes. We can't recommend Anna highly enough and will absolutely be booking her again. She treated our home and our pets like her own. 💛”
“Reagan took great care of all FOUR of our dogs over the weekend and treated them they were her own. She communicated often so we knew they were having a great time. We can’t wait to have her come back!”
About: One of the hardest things to do is trust someone to care for your pet, to make them feel safe, and treat them as family members while you’re away. That is the care I strive for with every visit! Because being away from your hoomans can feel uncertain, I provide extra play time and extra love. I also clean up their messes—if there are any, and I’m happy to help with the occasional chore when you have to be away for more than a couple of days! I am also committed to working closely with you to provide tailored care and companionship. I provide clear communication, pictures of your babies with each visit. I bring experience caring for pets of all ages—from playful youngsters to wise seniors—along with expertise in administering medications and supporting animals with special needs. Note: I’m no longer able to offer boarding services. One of my own sweet boys is getting up in years—he’s a little more fragile, and a little less patient than he once was, and I worry that boarding a stranger would cause him a lot of unnecessary stress. I work from home — this allows me some flexibility and the ability to customize my breaks and lunch based on the needs of my clients. When caring for pets in the home of my clients, it’s important to remember that the little one that I’m caring for is likely stressed because their mom and/or dad are gone, and there is a stranger (me) in their home. With that in mind, I typically spend more time with them than what is required by Rover because they need the extra time to feel comfortable with me. I take time to try to get to know them and help them feel more at ease. I treat them with the same amount of compassion I want for my own!
About: With your pets permission, they will be loved on. Pets in my care will be treated like family. I have been around pets of all kinds my whole life and have pet sat for over 5 years! The only days of the week where I’m out for more than 3 hours is Tuesdays and Thursdays. I am at home otherwise, the more time I have with your pet, the better! I do have two cats, so they will likely be separated from your pets in a boarding situation, but I live next to a dog park so it is easily accessible for pups. I have many cat toys and treat varieties as well.
“Kaitlyn did an amazing job and on short notice too. She came over before to meet and greet and was so pleasant and cheerful. Our fur babies were so well taken care of while we were out of town. She goes above and beyond and I so appreciate her. It made being away so much easier. Can’t wait to book you again our fur babies will definitely be well cared for.”
About: I will go above and beyond! Baths, walks, play time, and replenishing food if needed! No dog or cat is too much! Love al furbabies Currently coaching at EKU the cheer team and looking for some extra money! This is a dream job for me! Will watch at your house! I have 4 friendly dogs and they love other animals! Willing to do what it takes to take care of your animals! I’m free anytime!
About: I’ve had dogs ever since I was born, I love playing, walking and just handing out with them! Also i know the hardships it takes. I am a very available person, I do have a part time job but other than that I’m very free. I usually work a few hours every other day. I love going on runs which I enjoy very much to take a dog on, this could be a short walk or a hike! I’m very active but always love bringing animals with me even if it’s just to get a pup cup or play at a park!!! I currently have 3 dogs, and I watch my sister dog on occasion. My house has a fenced yard of an acre letting the 3 of them run freely. I’m very much for making an outside environment for dogs. But also believe in rest time. I usually spend time watching tv with my dogs or just laying with them
“Our dogs love Jessica and I know we can trust her with her with their complicated meds schedule. She sends photos and updates regularly and it is so precious to see her friendship with our dogs.”
“One of the best dog sitters we’ve had. Dogs were well taken care of. She took good care of our house and I am overall pleased with her services! She kept us well informed while we were gone. I would recommend Molly over and over again”
The median cost per night for house sitting in Winston is $40
Pet parents share their Rover experiences - Winston
Alicia has watched our pups 3x now. There was about a year between the first two bookings, so we requested her to come and “regreet” with them. As soon as they saw her, they went crazy. (in a good way) They clearly remembered her and missed her. She respects their very different personalities and sent us morning and nighttime updates. She also left our house clean with the sheets/comforter already in the wash. She was also very flexible as our plans changed during the 2nd booking. Highly recommended by both us and our pups.
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.
Meet local sitters who will treat your pets like family
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 near you
Select a filter and find qualifying Winston sitters!Sitters in Winston average 3 repeat house sitting clients
FAQs for House Sitting - Winston
Frequently asked questions about Rover
As of July 2026, there are 203 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winston. On Rover:
- 80% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 90% 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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