House Sitting Winona
Find a loving house sitter to watch over your pets and your home.
Over 66 pet parents in Winona have booked house sitting
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.
“Jillissa stayed overnight with my fur babies. She kept in contact and sent pics with updates. I felt very comfortable with her in my home and will not hesitate to book with her again!”
“Booked Peyton for both house sitting and drop in visits the week of 3/22/2026. She was great with taking care of my cat Turbo and providing pictures during my vacation.”
“Once again, 6 out of 5 stars from Rosie. This is our third time having Rosie take care of our three boys and every time we come back to fat, happy cats and a house that looks exactly like we left it. Perfect!!”
“Isabelle watched our three dogs while we were away for the weekend and did a great job! Our pups loved her, especially our pup that is usually very nervous around people he doesn't know. She was quick to respond to our initial request to have her pet sit and she sent lots of updates and pictures. We will definitely be asking her to watch our pups again for upcoming trips!”
“Jaxon recently cared for my two dogs in my home. He was positive, professional and a great communicator. This was my first experience on Rover and I could not be more pleased. I would have him care for my pets again in a heartbeat!”
About: I’ve pet sit for a long time! I often take care of a few dogs in my neighborhood and my next door neighbors cat. Ive always grown up around dogs so I know the responsibility of taking care of one. I always remember the details and I’m good at making a connection with pets. (dogs seems to always like me!). I enjoy bathing them and playing with them. I never forget to feed or take them on walks or outside for potty! Im currently in college at Winona but I am home for the majority of the summer. Starting July I’ll be up in Winona but can drive back if needed. I’d love to take care of your guys’ pets this summer, go enjoy a vacation. I often take care of my own dog! She needs play time and outside time. She gets the zoomies a lot so I always make sure to have her favorite toy out. Of course, I feed her twice a day as she needs. I’ll let her outside to go potty or play and keep an eye on her. I do bathe her every now and then to keep her clean and sometimes strip her fur if it’s getting too long. I love to keep a clean environment for pets so I always clean up/organize after!
“Arabella was excellent to work with and highly reliable with her care for our furry child! She is easy to communicate with including daily updates with photos! Moegly absolutely loved having her company. We will happily book her again for future needs!”
About: We’re Pawz & Play! We offer dog & cat boarding, weekend daycare, drop in visits, dog walking, and house sitting in Winona, MN. We operate on a small-scale, only taking a maximum of 2 pups or one family’s pets at a time. Erica is an aspiring dog groomer & trainer who someday hopes to have her own facility. Ciara is working on getting her bachelors and is the primary person on drop in visits. We have two medium sized young dogs who love to play & get along great with playful pups of all ages and sizes as well as an older small dog who does great with calmer pups. All dogs are assessed for play style and comfort level before being split into play groups. One of us is home the majority of the time and we incorporate your pets into our girls’ daily routine or we can do a rotation schedule if they’re not a fan of group activities. Our fenced in back yard has a good size dog run within the fence just for pups and the rest of the yard includes the chickens & rabbits in their own runs as well as a small patio, hammocks, and garden beds. Whether in your home or ours, we are happy to serve your pets whatever food you’d like including homemade, raw, canned food, or kibble. We just ask that it be premade so we need only measure out the amount and feed your babies.
“A repeat experience with Ajia did not disappoint. While she was walking him, he had a minor accident that left a small cut. It could have happened to anyone. Ajia took it very seriously - called me immediately, sent pictures, treated the cut and made sure he was ok. She immediately reported it to Rover, per their guidelines. When I got home - it really appears to be just a surface cut. However, this experience gave me complete confidence that if anything serious were to happen, she is the right person to be able to address it in our absence. She is wonderful and will continue to be our #1 pick for our cranky old man!”
“Laren stayed for a 3 day weekend with our 3 dogs and 2 cats. She did a fantastic job. She followed through on all our instructions and requests. She was prompt in returning messages and sent us photos too. She even made friends with our very shy cat who will normaly never even be around strangers. She's truly a "cat whisperer"! We recommend her highly!”
“Christie was great to work with and great with our kitty! I was so worried about leaving my young kitten for a week but she made the experience stress free. She provided several updates and lots of pictures! I would recommend her to anyone looking for someone trustworthy to stay with their pets and in their home!”
“Jacque was wonderful while staying with my puppy Atlas for the weekend! She provided me with great updates and pictures. I could tell Atlas really liked her and he was the same happy, sweet pup when I returned home!”
About: Hi! My name is Angela, and I understand how important it is to know your pets are safe, loved, and comfortable while you’re away. I have experience caring for pets in their own homes and believe that remaining in a familiar environment helps reduce stress and anxiety for many animals. I’ve previously provided overnight pet sitting for multiple clients and enjoy creating a calm, consistent routine that keeps pets happy while their families are away. As a healthcare professional, reliability, communication, and attention to detail are a big part of who I am. Whether your pet needs walks, playtime, medications, feeding schedules, or simply companionship, I will treat them with the same care and respect I would want for my own pets. I am the proud owner of two cats and understand that every animal has their own personality, preferences, and needs. I enjoy spending quality time with both dogs and cats and will keep you updated with messages and photos so you can relax knowing your pets are in good hands. I look forward to meeting you and your furry family members! I work full-time Monday through Friday, but I am available for weekend house sitting and pet care. If you are located in Viroqua or La Crosse, I may also be available for weekday house sitting and pet care. When caring for your pets, I follow their normal routines as closely as possible to help them feel comfortable and secure. I provide regular updates, photos, and communication so you can enjoy your time away knowing your pets are well cared for. I primarily provide care in my clients’ homes because I believe pets are happiest and most relaxed in their familiar environment. I take time to learn your pet’s routine, feeding schedule, medications, exercise needs, and preferences. As a healthcare professional, I value reliability, attention to detail, and clear communication. My goal is to provide safe, compassionate care while treating your home and pets with the utmost respect.
“Eliza was absolutely terrific. She was so patient with our senior dog (15 yrs old) Also, our new rescue (9 yrs old) we have been workibg on house training her. Eliza spent the nights here as well (which not all dog sitters will do). I would highly recommend Eliza. She was here for 7 nights 8 days. Great personality and easy to communicate with. Bonnie”
About: I’ve been caring for animals my whole life and have 4 years of professional experience from working at an animal sanctuary and currently a vet clinic! I am also going to school in Rochester to become a veterinary technician! Having a dog and two cats to care for of my own and currently working at a vet as a vet assistant. My days always consist of caring for animals and I wouldn’t change it for anything. At home I have another dog who gets along well with other dogs and people. I also have 2 cats but they are outdoor only and are used to dogs. I have a big house with an even bigger yard. I can take your dog on walks or hikes and they will get plenty of exercise. Inside the dog will have its own space and I can crate your dog if needed. I am willing to work with any accommodations you need for your furry friend.
About: I have worked at a boarding kennel for dogs/cats, it made me so happy and everything in my life disappear when I'm with them daily. I’m currently working part time at the moment but I will check up on them and make sure that everyone is doing okay before work! I live in a trustworthy neighborhood in a house with my boyfriend! There is plenty of space for them to run around and get their energy out!! If you have any questions about my housing, please ask away😁
About: I grew up on a farm and I have experience with multiple different breeds of animals. I take the time to listen to animals and their body language. I work part time. So i have plenty of extra time to spend and care for your fur baby. Im available Monday to Friday after 2pm and weekends! I have plent of yard space and easy access to walking tails and parks. I do have a dog friendly cat who can keep ur fur baby company
The median cost per night for house sitting in Winona is $40
Pet parents share their Rover experiences - Winona
Naomi was fantastic with our boy Junior. We booked her to spend the day and night with him on our wedding day and she went above and beyond sending us so many updates and notes about how he was doing and what they were up to. We will definitely be rebooking in the future!
Skylar absolutely saved the day for me when another Rover sitter had to cancel a few hours into the first day of a three day house/dog sit. I was already hours away from home and she worked with me remotely to effect a smooth handoff. It was a huge relief after a stressful afternoon! She took great care of my two pups and kept the house tidy. She sent me photos and was good about responding when I would check in periodically. Already planning to hire her for my next trip!
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 near you
Select a filter and find qualifying Winona sitters!Sitters in Winona average 3 repeat house sitting clients
FAQs for House Sitting - Winona
Frequently asked questions about Rover
The average cost for House Sitting in Winona on Rover is $32.1 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of July 2026, there are 176 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
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