House Sitting Winfrey
Find a loving house sitter to watch over your pets and your home.
Over 35 pet parents in Winfrey have booked house sitting
Winfrey, 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.
“Farrin is an amazing petsitter! She stayed all day with our lab (who gets very anxious when we are away) and two kitties. We were able to enjoy our son's wedding without worrying how our pets were doing. This is our second time booking with Farrin; both times she has communicated well with us before the event as well as sending us updates (texts & pictures) during the actual house/petsitting.”
About: Hi! My name is Kylie, and I’m an animal lover with years of hands-on experience caring for pets of all kinds. I currently have one cat, Nova, who keeps me company, but I grew up surrounded by animals, including cats & dogs. My professional experience includes working for 5 years as a kennel technician at a boarding kennel in Culpeper, where I cared for a wide variety of dog breeds, personalities, and energy levels. During my time there, I gained valuable experience with feeding, exercise, cleaning, monitoring pets’ health and behavior, and administering medications to dogs who needed them. I understand that every dog is different, and I strive to provide care that fits each pet’s individual needs and personality. Whether your pup needs a walk, some playtime, companionship, or simply a little extra attention while you’re away, I’m happy to make sure they feel safe, comfortable, and cared for. Your pets are family, and I treat them that way! I look forward to getting to know you and your furry friends. 🐾 I’m available anytime for drop-in visits to care for your pets, ensuring they receive the attention and love they need while you’re away. I appreciate your interest, but I currently do not provide pet care in my home. I focus on drop-in pet sitting for your furry friends.
“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’ve taken care of dogs and cats of all ages and provided medications when needed including pills, eye drops, and shots! I also am flexible to what your pet’s routine already is! I’m home for summers from college (Go Dukes) and I’ve always loved animals, so pet-sitting is my only job over this time! I’m available all days throughout the week! When you’re vacationing in the summer I will look after your pets and give you peace of mind with pictures I take of them and I always leave your house looking like I was never even there!
“Catherine provided great care to our 2 pups! She stayed with them for a long time every visit and sent regular pictures and updates to keep me in the loop! Will definitely use her again to look after our dogs :)”
About: I love dogs and am very passionate about care and safety of the animals I care for. I have gotten two of my own dogs through obedience training and canine good citizen testing. I also have experience, 13 years, living with dogs actively training and competing in IPO. Easy or difficult dogs areno problem. I can take direction and care and interact with your dog exactly as you'd like. I can give potty breaks during the day and am available to stay overnight in your home with your animals. I am also available on weekends and can give potty breaks more often if needed. I vary my care depending on what the client wants but id prefer a dog on my lap watching a movie. Well exercised and fed!
“Erica was great! She was great with my dogs and constantly updated me. I came home to a clean house and happy dogs. Thanks so much Erica and hope we can use you again!”
About: I have been taking care of the animals of close friends and family since I was 19 years old. In addition to taking care of cats and dogs, I am also an experienced farm hand. I have taken care of horses, chickens, donkeys, and Alpacas. Whatever your pet needs are, I can do it. I am currently doing volunteer work on Tuesdays, but am available every other day of the week. Early mornings and afternoons work best for me, but I am available later in the evening when needed I can do feedings, walks, drop ins, and full night stays. I can also administer oral medication. I have a dog of my own and she gets daily medication I give her myself.
“Makaylah did a fantastic job taking care of my dog, Gunnar. I needed her last minute for a weekend stay when my usual pet sitter had a family emergency, and Makaylah was very responsive and immediately set up a meet and greet. She knows a lot about dogs and was instantly comfortable with Gunnar. She asked all the right questions and sent me frequent updates, which I appreciated. I came home to a happy dog and a clean house - what more could you ask for? I will definitely use her again, and can highly recommend her services.”
“We had an amazing experience with Melissa! She stayed in our home for a week with our two dogs, one of whom has severe anxiety. She took the time to do a meet-and-greet beforehand, gave him the space he needed, carefully read his body language, and earned his trust. She was reliable with his daily medications and patient in helping him feel comfortable. Our home was left spotless and respected, and it was clear she treated both our dogs and our space with great care. She even surprised us with a kind and thoughtful gesture at the end of the stay, which meant so much to our family. We are so grateful to have found her and would 100% book with her again. Highly recommend to anyone looking for a caring, dependable, and professional sitter!”
“Star and Jack did an amazing job taking care of my senior girls. This is my first time using them and will definitely rebook. I felt so confident that my pups were getting the ABSOLUTE best care while I was away. So happy that I book them!”
About: I’ve been caring for dogs for over 8 years, and it’s something I genuinely love. I’ve worked with dogs of all ages, sizes, and personalities from energetic puppies to senior dogs who need a little extra patience and care. I also have experience caring for dogs with medical needs, so I’m comfortable following detailed care instructions, administering medications, and paying close attention to any changes in behavior or comfort. Friends, family, and neighbors have trusted me to walk, feed, and care for their pets, and I always treat every dog like they’re my own. I prioritize keeping their routine consistent so they feel safe, happy, and well cared for while you’re away. I also have volunteered in the past with being a temporary foster for shelter/rescue dogs. I also have volunteered with driving dogs in rescues to their medical appointments. I’m reliable, communicative, and respectful of your home and your pet’s needs. Whether your dog needs a long walk, extra attention, or more specialized care, I’m here to help. I have a flexible schedule that allows me to give your dog the time, attention, and consistency they need. I’m available for walks, drop-ins, and sitting throughout the week, with more open availability in the afternoons and evenings. I do my best to accommodate your pet’s routine and can provide reliable, timely care you can count on. Your dog’s safety and comfort are always my top priority. I take the time to understand each dog’s routine, personality, and any specific needs including medical care or medications. I follow instructions closely and keep a watchful eye on behavior to ensure your dog feels secure and well cared for. In your home, I’m respectful of your space and maintain a calm, clean environment. On walks, I stay attentive, avoid unsafe situations, and ensure your dog is always secure. I’m also happy to provide updates so you feel at ease while you’re away.
“Deborah has taken care if my two Springers a few times. She takes wonderful care if them, and sends me updates and pictures frequently during the stay. I always come home to very happy dogs!”
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:)”
The median cost per night for house sitting in Winfrey is $50
Pet parents share their Rover experiences - Winfrey
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
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 - Winfrey
Select a filter and find qualifying sitters offering house sitting.Sitters in Winfrey average 3 repeat house sitting clients
FAQs for House Sitting - Winfrey
Frequently asked questions about Rover
The average cost of House Sitting in Winfrey on Rover is $48 per night as of October 2026. Most bookings cost between $21 and $74 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 557 sitters on Rover offering House Sitting across Winfrey. 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 Winfrey 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 Winfrey 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 Winfrey 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 Winfrey. 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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