House Sitting Winner
Find a loving house sitter to watch over your pets and your home.
Over 57 pet parents in Winner have booked house sitting
Winner, 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.
“I cannot recommend Jason enough as a dog sitter! From the moment we met, he made me feel completely comfortable leaving Dax in his care. Jason was incredibly accommodating and went above and beyond to ensure both Dax and I had peace of mind. He kept me updated with plenty of photos and videos, which showed just how much Dax loved his time with Jason—especially all the playtime! It's clear Jason truly cares about the dogs he watches. If you're looking for someone reliable, attentive, and genuinely kind, Jason is your person. Dax and I are so grateful for him!”
“Olivia was absolutely fantastic while we were on a family vacation! She took care of Stevie and loved her as her own while we were gone. She also took great care of our house and left it cleaner than when we left for vacation. We will absolutely book services again with Olivia and highly recommend her.”
“Kaylee was wonderful! First time using her and we have zero complaints. She even took care of our chickens, got their eggs each day, and loved on our old pupper. Recommend to anyone!”
“Emily was awesome! We were using Rover for the first time and she was so helpful! Our dogs absolutely loved her at the meet and greet:)! She kept us updated during our entire trip and the dogs were super happy!!! We couldn't have asked for more…we will be asking her back for next year!!!”
“Emily was wonderful. She kept me up to date and sent pictures. I actually relaxed while out of town and didn’t worry about Fiona. Emily went above and beyond, she even ran the dishwasher and stripped her bed. Highly recommend Emily.”
“Lauren is amazing! She communicated regularly and sent pictures to us throughout our vacation. Our dog was well cared for and happy when we got home. We will absolutely book with Lauren again and recommend her to our friends!”
“Lilia was amazing with our rescue pup, Berkley! She is super calm and kind - we could tell our Berkley already felt comfortable around her the first time she met her! She sent us many photos throughout the weekend. She was very communicative and professional. We would recommend her to any friend or family member!”
About: I have been a dog owner for most of my life, but do not currently have one. I miss having a dog and the companionship they provide. This is why I am hoping to help take care of yours when needed :) I was a dog groomer for about 3 years and loved every minute of it! I'm available to take care of your pet early in the morning, afternoon with advance notice on weekdays, evenings, and nights as well as weekends and holidays. I am open to providing drop-in care, dog walking, and grooming services - whatever you need for your beloved pet. We can discuss when, where, and how you're comfortable with me providing these services.
About: Hi, my name is Philip and I love dogs. Through my life so far I have always been jealous of my friends whose parents allowed them to have a dog. But I take every opportunity that I can to play and care for dogs That being said, I have helped care for a couple of neighbors dogs and take them on many walks. One of them was German Shepherd puppy that I even was able to train and I grew quite attached. Whenever I am able to move out I plan to get a German shepherd for myself because of how much I loved my neighbor's puppy. I am currently working part time so I have a good bit free time on most days. I can walk or dog/cat sit weekdays and weekends most of the time until I get a full time job! I can care for a pet in your own environment however you would like me too, I'm very open and flexible as long as I have clear instructions and resources. I'm up to almost any task!
“Thanks goodness for finding Grant! I had a family emergency and I needed to leave the country in a day. I am new in town and I didn't know anyone. I got on rover and I started sending requests. Grant responded promptly and he was ready to be interviewed by Shadow, my service dog. It was love at first sight. Shadow is a really great dog but one has to be really careful about his diet and about his medication schedule. Grant did great! He is a young man who loves dogs and will go out of his way to accommodate the clients needs. He babysat my dog at my place and he answered my calls consistently. Grant has my highest recommendation. Don't think twice about leaving you pup in his living hands.”
“Daniel was fantastic! He took amazing care of both our dogs, cats, and house. It was the most stress free experience I’ve ever had on vacation. He sent daily updates and photos, tidied up the home, and followed our dog’s routine making it a seamless transition. Our rescue who struggles to be around new people warmed up to him quickly. I highly recommend Daniel! We will definitely be using him again for any future trips.”
“Kristen took time to come meet our dog Vinnie who is slow to warm up to new people. She is great at communicating and adapted to our power going on and off. Sent pictures of fur babies and kept us updated of how things were going. Definitely would have Kristen again as our pet sitter!!”
About: my friends and family joke about me being a crazy cat lady .. which is funny but true!! I’ve had cats and dogs since I can remember and my phone is full of pictures of my own pets. I pride myself on the care and attention I pay to animals. Along with open communication with you to make you feel at ease as I take care of your furry friend. I have babysat for families for the past he ten years which has led me to start pet sitting. I have always had pets, ever since I can remember .. cats and dogs! I enjoy dog and cat snuggles and spending time with animals. I work as an architectural designer and volunteer at KCPP in my free time! I work a traditional 9-5 (ish) job but love to squeeze in time with animals! I will treat not only your pet but your home like it is my own. I will tend to any messes created by or in relation to your pet and try and leave it better than it was found!
About: I’ve taken care of animals since I was a teen. Family, friends, and neighbors can count on me to walk, feed, bathe, & any other extra care their pets need. I’ve taken classes for basic dog training & behaviors. I’m currently working part time so I have plenty of time to care for your pup! I’m available on week days & most weekends. I’m flexible & can work with your schedule. I can do multiple drop ins a day, house sit and stay with your animals over night, or they can be dropped off at my home.
“Jessica was such a wonderful dog sitter for us! Our dog was so well taken care of, and got lots of walks at various parks. Jessica is an excellent communicator and sent us photos while we were away. We returned to a clean house and a happy pup. We can't thank her enough!”
“Claire took care of my geriatric dogs who have eating issues. I believe that she was patient and tried any way to help them eat. She was here a full week and I came home to a clean house. We will use her again!”
The median cost per night for house sitting in Winner is $50
Pet parents share their Rover experiences - Winner
Tania was a perfect housesitter for our GSD Nova while we were away for a multi-day ski trip. She was very flexible with us as we were struggling to leave and return on time, and was willing to help when a special delivery was scheduled for us while we were away. Nova seemed to really like her, and she was excited to run through training sessions with Nova each night. She also provided some of the best photos of Nova we have ever seen! I would absolutely recommend Tania to anyone.
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 - Winner
Select a filter and find qualifying sitters offering house sitting.Sitters in Winner average 4 repeat house sitting clients
FAQs for House Sitting - Winner
Frequently asked questions about Rover
The average cost of House Sitting in Winner is $50 per night as of October 2026. Most bookings cost between $33 and $80 per night. On Rover, 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 1,310 sitters on Rover offering House Sitting across Winner. 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 Winner 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 Winner 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 Winner 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 Winner. On Rover:
- 91% 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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