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!”
“Madison is amazing! She’s watched our dog and house twice now, both times on short notice, and has been wonderful. She’s reliable, responsive, and takes such great care of our pup. We always feel totally comfortable leaving everything in her hands and will definitely book with her again!”
About: I’ve been pet sitting and caring for dogs and cats for over 20 years, and I can genuinely say there are few things that make me happier than getting to know a new furry friend. I currently run my own pet-sitting business and have been incredibly lucky to build a wonderful little family of happy pets, repeat clients, and pet parents who trust me with their babies. I know every pet is their own little person! Some want to play fetch until your arm falls off, some want to be your shadow, some would happily spend the entire visit getting belly rubs, and others need a little extra patience and time before deciding you’re worthy of their friendship. I love learning all of those little quirks and keeping their normal routines as familiar and comfortable as possible while their people are away. I have experience with dogs and cats of different ages, sizes, personalities, and needs, including multi-pet households and routine oral and topical medications. And because I know how much you miss your babies when you’re apart, I’m a BIG believer in sending plenty of photos and updates along the way! Your pets won’t just be fed, walked, and checked on…they’ll get conversation, playtime, companionship, scratches, cuddles, and plenty of love. My goal is for you to be able to enjoy your trip or get through your workday knowing your pets are safe, comfortable, happy, and being genuinely cared for. Loving Your Pets Like They’re My Own isn’t just my slogan, it’s exactly what I try to do with every animal entrusted to me. 💕🐾 Pet sitting is already a regular part of my weekly routine, and I currently have a very flexible schedule that allows me to devote plenty of time to the pets in my care. I’m available weekdays, evenings, weekends, and overnight, and can often accommodate extended stays as well. Whether your pet needs a quick drop-in, some company during a long workday, or someone to stay with them while you’re away, I love being able to plan my schedule around their normal routine. When I’m caring for your babies, they’re never treated like something I need to “fit in.” Spending time with them is the best part of my day! 💕 I provide care in my clients’ homes because I believe pets are often happiest and most comfortable in their own familiar environment. I take the time to learn each pet’s normal routine, personality, feeding and potty schedule, favorite activities, medication needs, and any special instructions their family provides. I’m respectful of both your pets and your home, and their safety and comfort are always my priority. I never force interaction with a shy or nervous pet…I’m happy to give them the time and space they need to decide that we’re friends! While you’re away, I’ll provide plenty of companionship, playtime, conversation, scratches, cuddles, and love, along with lots of photos and updates so you can see how your babies are doing. 🐾💕
About: From seniors, to unsure, to feral, to kittens I’ve dealt with & shown love to all spicy, reserved, or full of love they are all the one for me(: I have a flexible job, I work as I choose so I’m available for you and your fur babies whenever I am possibly needed (: I’ll provide them fresh food and water, bathroom breaks, cleaning, entertainment & enrichment I’ll provide them there medications and companionship as well as nice walks
About: I have taken care of dogs and cats for 20 plus years for friends and family along with my own pets which include two dogs and three cats. I have trained dogs from early puppy stages and also cared for senior ages. I work Wednesday Thursday Friday I’m available after 7 pm I’m off Saturday Sunday Monday Tuesday available anytime. I’m offering drop ins, sitting and walking! Your fur babies will definitely be loved and get their playtime in along with lots of treats if allowed. I have had many animals growing up dogs, cats, lizards and even a raccoon 😃 I have trained dogs from their puppy stages and loved every minute of it. You can trust that ur babies will be in good hands.. ❤️ I am currently working but I have plenty of time to give my full attention and time to your fur babies. I am available weekends! I have a big yard for your fur babies to run around in and also two dogs of my own to play along. I am also able to crate if needed!
“The first time we left our 3 dogs and 2 cats in the hands of a sitter. Tabatha was amazing! The pets had no hesitation in welcoming her into our home and enjoyed having her here. She provided great care, communication and pictures during our time away. Thank you Tabitha!”
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.
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 - 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 October 2026, there are 287 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.
<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 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 , 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 Winona. On Rover:
- 95% of sitters can help with special care needs
- 96% 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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