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

Winona, 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.
“Kori did a great job! She set up a time to come out and meet my puppy before booking & kept in touch all night sending me pictures and keeping me updated. I work night shifts and don’t get home till 3 am and thankfully Kori stayed up with Jameson all night while we work through house training him!”


“Amanda was great with our three Husky’s. They are all blowing their coats and she did a great job keeping up with the flying fur. Our dogs were so calm and relaxed when we got home, she did a great job of keeping me updated and I didn’t have to worry about whether or not they were well cared for during our vacation!”

“Erica was so flexible with my schedule! My animals loved her and even my cat who never comes out and visits people came to visit her! She made time to play with my dog to be sure he was stimulated and worn out. I would use her again.”

“Britnie was amazing! I was super nervous about leaving my fur baby and she eased my mind so much. She sent so many updates, cute pictures, and communicated so well. She definitely spoiled her and gave her all the love while I was away. Super thankful for her help!”

“Marcy did amazing with Theo. It was my first time leaving her outside of our family and my mind was completely at ease. Marcy sent updates and photos regularly which was fantastic! I returned home, tired and jet lagged, to a happy, healthy dog and a tidy house. I will be HIGHLY recommending her and will definitely have her return in the future.”

About: I grew up with dogs, so i have taken care of them my whole life. I have also helped out friends and family members with dog sitting. I am currently working part time, so i have plenty of free time during my day to take care of your animals. I can stop by frequently or house sit as well. I have two dogs and i take care of them by feeding them, letting them out, making sure they have water, walking them, etc. i am very good with animals, and enjoy spending time with them.
About: Current YSU education student. I’m a reliable, patient, and detail-oriented pet sitter who treats every pet like they’re my own. I’m happy to provide walks, potty breaks, playtime, feeding, and drop-in visits while following each pet’s individual routine and needs. I’m also big on communication and will keep you updated with photos and messages so you can feel confident your pet is happy and cared for while you’re away! My current schedule allows me to provide pet care after my student teaching day and on weekends. I’m available to stop by for drop-in visits, potty breaks, playtime, or walks after work, and I have more flexibility on weekends. I enjoy having a reason to get outside and would love to make sure your pet gets the attention, exercise, and care they need! I prioritize your pet’s safety, comfort, and individual needs during every visit. I carefully follow your instructions and your pet’s normal routine, including feeding, walks, potty breaks, and playtime. I’m attentive to my surroundings and make sure pets are secure before leaving. I’ll also provide updates and photos so you know your pet is safe, happy, and well cared for while you’re away.
About: I can feed, walk, and play with your pets, clean litter boxes, provide fresh water, and take care of anything else they may need! I’m also comfortable giving medications and have experience caring for diabetic dogs. I’m happy to provide loving, reliable care and make sure your pets are safe, happy, and well taken care of while you’re away! 🐾❤️ I currently work 4 days/week in the evenings at a barn(4 days/week; 2 hours/day) and I just got a job at Amazon! I can give your animals all the attention and loving they need! I can crate your dog if you need me to. Safety of all animals is my first priority before anything else comes in to play!

About: I have taken care of dogs ever since my 20's but the last 13 years I have been house/dog sitting for the members of the congregation were I was paid staff. I absolutely love animals but dogs are my favorite. I have extensive experience with any breed from puppy to geriatric dogs. My goal is eventually to do boarding as well. I would love to come stay with your pet baby and love on him/her while you are away. I believe in spending time with the pets. I promise you I will become your pets best friend second only to you. Getting them some exercise every day if possible and lot's of cuddle's at night. I prefer clients with fenced in yards. I am currently not working so I will be with your pets through out the day. Recently my daily schedule has opened up so I would be with your pets full time. If you dogs like to ride in the car I would take them on errands with me. Really there are no obstacles for me to be able to be with you pets full time. I am looking for full time remote work from home work though. Then I can still do dog sitting at the owners home or my home while I'm working. The first thing I do when I get up around 8 or 9 is let your dog outside if it's a fenced in yard a walk if it's not. Then I feed them per whatever instructions you have left. In the afternoon we go out again for some play time and potty break. I usually will let the dogs out an hour after they eat and every 4 hours a day, For cats, I feed them first thing. Keep their litter box cleaned daily or every other day and depending on the cat's acceptance of me or their personality we will have play time and cuddles too.
“I recently had the pleasure of hosting Jeannine for house sitting services. I cannot begin to express how impressed I was in her care for my senior dog, Jade, while I was away. I was provided frequent text message updates, including photos which were nothing short of professional grade. She politely provided me expertise and pointers regarding Jade’s feeding, and even detected and treated some minor health issues. She laundered and neatly folded everything she used, and seriously left the house in better shape when she departed. I chose her services based on previous recommendation from Rover clients, and was definitely not disappointed. I knew from the moment I met her that she possessed the maturity and integrity I was looking for in a house sitter. I highly recommend Jeannine for care of your pet. Bob B”


About: I have years of experience caring for dogs and other pets and genuinely enjoy spending time with animals. I’m reliable, attentive, and committed to providing a safe, fun, and loving environment for every pet in my care. I understand that every animal has unique needs and will work to keep your pet comfortable and happy while you’re away. I am currently a full time online college student and volleyball coach, so I will have plenty of time to attend to your pets! have a flexible routine that gives me time for feedings, walks, drop-in visits, playtime, and companionship throughout the day. I prioritize clear communication and will make sure your pet receives the care, attention, and routine they are used to while you’re away. When caring for pets in my client’s home, I focus on maintaining their normal routine to help them feel comfortable and secure. I provide fresh food and water, walks or playtime, litter box or waste cleanup, and plenty of attention based on each pet’s personality and needs. I also keep owners updated with photos and messages for peace of mind. When caring for pets in my home, I provide a safe, clean, and welcoming environment where pets can relax and feel at home. I closely supervise them, follow all feeding and care instructions, and make sure they receive plenty of exercise, enrichment, affection, and rest. My goal is to treat every pet as if they were my own and ensure they are happy, comfortable, and well cared for.
About: Each and every animal that I come in contact with I am respectful and calm! I love every pet like it’s my own. Each dog requires different needs and I am completely understanding and will do what it takes for the animal to be the most comfortable and relaxed it can be. I am grateful for the love animals give me and I hope that I can give them that love back. Animals are part of families and I want to provide that comfort when their families are not around! I have expierence with being around all different animals since I was very young. I have been dog sitting since I was 13 years old. I have the experience you want for your loved family member. I work at a veterinary clinic so I have experience with working with all types of breeds. Being a vet assistant I am able to provide for your pet with the knowledge and confidence it takes to take care of any pet!! I work full time at a vet clinic and love to surround myself with all types of different animals! I find comfortable and peace giving people the option to have someone love their pets as my own when they are away! Any needs that your pet may need I am more than comfortable to provide. I deal with many different species and behaviors daily at my job and would love to do whatever your pets need to be comfortable.

About: I have taken care of different dogs through the day and overnight. I enjoy meeting new dogs and learning their personalities. I also have two dogs of my own that I love to take on walks, play outside, and go on little trips with!! I currently work part-time, which gives me a flexible schedule and plenty of time to care for your pets. I am available for walks, drop-in visits, daytime care, and overnight stays. I enjoy spending time with dogs and making sure they get the attention, exercise, and care they need while you’re away. I treat every dog as if they were my own. I have two friendly dogs and I make sure all pets in my care have plenty of exercise, playtime, attention, and a safe environment. I am happy to follow your dog’s normal routine, including feeding schedules, walks, medications, and crate training if needed. I want both you and your pet to feel comfortable and confident while you’re away.
About: I work from home, so pets get consistent attention, supervision, and companionship throughout the day. I provide a calm, structured home where animals feel safe and included in daily life. I’m attentive to routines, exercise, and individual pet needs, and I treat every pet like family. I also have experience in home care work, which strengthened my responsibility, patience, and reliability. I work from home Saturday through Tuesday, so I’m available throughout the day for walks, potty breaks, and lots of attention. I’m also off Wednesday through Friday, which gives me even more flexibility for drop-ins, walks, or extended care. Because I’m home most of the time, your pet won’t be left alone for long periods and will get consistent care and companionship. I provide a calm, safe, and loving home environment where pets can feel comfortable and relaxed. I take introductions slowly and make sure all animals feel secure, especially when meeting my dog. I have a sweet Great Pyrenees mix who is gentle, affectionate, and does best with smaller or calm dogs. Your pet’s safety and comfort always come first. My dog is up-to-date on vaccinations and flea/tick prevention, and I always follow owner instructions closely to make sure your pet’s routine stays consistent.
The median cost per night for house sitting in Winona is $50
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
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Popular requests for house sitting - Winona
Select a filter and find qualifying sitters offering house sitting.Sitters in Winona average 4 repeat house sitting clients
FAQs for House Sitting - Winona
Frequently asked questions about Rover
As of September 2026, there are 295 sitters on Rover offering House Sitting across Winona. 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 Winona 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 Winona 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 Winona 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 Winona. On Rover:
- 100% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 92% 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.






