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

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Top rated Winterset house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Allison recently stayed with Maisie again for 4 days. I say “again” because we are repeat customers of Allison’s. she is such a great dog/housesitter. I know I can travel without worrying about Maisie’s care and without the hassle of taking Maisie someplace else. And the condo is spotless when I return. Thank you Allison!”


About: Growing up, my family didn’t have pets, so I love my friends and family’s pets like they are my own! I am intentional and ask questions when learning from owners how to best interact with their pet(s). I’ve taken care of both dogs and cats, up to two of each at the same time. I prioritize playtime and being active with any pet I’m responsible for. I’m comfortable with both cats and dogs, and can adapt my skills and schedule based on their unique needs. My schedule is extremely flexible as I continue the job search post graduate school. I am able to support pet owners with short-term drop ins, frequent walks for high energy pets, and extended stays. I am available to care for pets in their own home. I aim to ease any stress by keeping their environment familiar and maintaining their usual schedule as much as possible.

About: I've pet/house sat for multiple people in the past. Animals include dogs, cats, fish, and reptiles. I like to have a meet and greet before ever staying with your pets alone. If you have any special diets or quirks make sure we discuss them in advance! I don't mind staying for a few hours to watch your animals or just drop in, whatever is needed! I have a nighttime job so, your animals will need to be able to be alone at night a few days of the week! I will discuss meal plan, how often you walk them/let them outside, and if they have meds with you prior to caring for your animals.
“Yasmin took excellent care of my dog during a week-long trip and I would definitely book with her again! Ranger gets anxious sometimes, especially when his routine is disrupted, but he seemed happy and content in all of the picture/video updates (and I appreciated her sending those regularly). Thank you for keeping my best friend happy and healthy while we were gone, Yasmin!”

“Nothing but AMAZING things to say about Mackenzie and Anthony who took the time to watch our sweet boy Tiger! We were new to the Rover app and had some anxiety, but Anthony provided updates with photos and videos throughout the entire day! We are so so thankful! Anthony went above and beyond!”

“Sam took care of our home and four dogs for a week and a half and did such a great job! She was great at communicating and sending photos, and you can tell she loved on the pups hard while we were gone! We will absolutely book her again!”

About: I have dog sat my friend’s dog, her aunt’s dog, and my sister’s dog. Dog sizes range from small to large. I love taking dogs for walks. I also love snuggles just as much. :) I would be available Thursday night after 5:30 to Sunday evenings. I currently work all day Monday, Tuesday/Thursday afternoons (12:30-5:30), and Wednesday mornings (7-12). I am off on Fridays. I live in a secure condominium. The front and side doors are both locked on the building at all times. Only homeowners have keys. I have stayed in other people’s houses as well. I always make sure to leave the house looking clean when I’m done dog sitting. That way you don’t have to worry about cleaning up after me upon returning home.
About: I am currently working part-time at a reputable dog boarding kennel. In this role, I have gained valuable experience in various aspects of dog care, including administering medications, closely monitoring behavior, and providing exceptional care for dogs of all ages and sizes. My dedication and passion for ensuring the well-being of these furry companions have allowed me to develop a deep understanding of their unique needs. I am able to work from home on Mondays through Wednesdays, which allows me the flexibility to balance my responsibilities. On Thursdays through Sundays, I am fully available in between my shifts at the kennel, ensuring that I can handle any tasks or commitments that come my way. This arrangement enables me to efficiently manage my time and fulfill both my work-from-home responsibilities and my duties at the kennel. When I am in your home, you can rest assured that I will go above and beyond to ensure your beloved pet is not only happy and safe but also thoroughly entertained. Your furry friend will be pampered and cared for in the utmost luxury, providing them with the ultimate comfort and peace of mind while you are away.
“Kaitlyn did a wonderful job taking care of our 13 yo female dog in our home while we were away. Kaitlyn took care of all of her needs, including medication and left the house without a trace she was there. Would definitely rebook with her.”

“Tiffany did a great job taking care of our pets and small hobby farm. She communicated regularly before, during, and after our trip. Tiffany was also flexible when unexpected things came up. I will definitely be booking with her again!”
About: I have worked with cats and dogs of all sizes and ages, I strive to provide the best experience for not only the pet but the pet parent as well! I have experience working at the Animal Rescue League alongside my own animals and friends and families animals I’m an open availability sitter I will always put the needs of someone’s animals at the forefront of anything! I have all the time and attention in the world to give your babies I love taking my boys on walks, to the park, and love giving them a variety of enrichment throughout the day! We love exploring and trying new things at a comfortable pace for the animal! I can also follow a schedule and I’m flexible with whatever the pet parent needs to give the most ful filling service
About: I’ve been & lived with animals all my 25 years of life so very keen to wants and needs—play, sleep, walks, food. What we all want as humans as well. Just look for a furry companion to share my time off with! I’m a nurse who works 3 days a week, so have a lot of downtime! Would love to talk your special loved ones on walks around this beautiful city! I have no pets in my luxury apartment so all my time and attention will be on your pet. We do have a fenced in area for easy restroom breaks.
“We love Jess! We have three dogs a 11 year old pug who is having issues getting around, 7 year old Pug who is a rescue and a 6 yr old chihuahua mix who is also a rescue both with some separation issues. It was such a relief to know they could all stay in our home while we were out out town. Jess was wonderful, we got pictures and update from her daily and the dogs were so well taken care of. We look forward to using her again!”

About: I have spent much of my life taking care of different animals. I grew up on a farm handling chores for animals of all kinds from horses to dogs and cats. I currently have a 3 year old Maine Coon cat named Boston! I currently work mornings, typically 7-3 M-F. My hours vary depending on the week and what I am busy with at work. I work shifts on weekends and nights when needed I have a yard for your pet to run around in and play. I do have 3 other pets in my home that are properly vaccinated and friendly!
About: hi my name is bonnie i live in new virginia,born an raised in Maryland, I have two kids and two successful small business one cleaning houses after i left health l care an other is family wedding venue, I grew up on dairy farm back in Maryland we had every farm animals and pets. my parents also bread Golden retrieves for 15 years,I have bunch of stray cats come across highway an stay i have always taken them in .I love animals very peaceful creatures and best friends,my clients have pets they all run up to me get excited to see me. Im hard working and behind trustworthy and honest. I have never dog sit or anything like this but I'll figure things out fast, fall and winter time is my off season from venue im looking stay busy since I hate sitting around, thank you hope to hear from you soon I'm house cleaner but I am now able pick up more hours doing something different. so I can pet sit or anything during weekday while my kids are in school possibly evenings. weekends I have nothing to do. the clients will tell me how they want things done .my animals are on farm they run wherever they please. I will read the plans they set for me.
About: I've had dogs, cats, rabbits, & guinea pigs for pets all my life. (515) In the last 5 years I started staying and house & pet sitting while people are on vacation or away. (448) I care for ALL animals including handicapped pets. (2549) This company rips you off with fees & extra charges, so call or text me. I'm available almost 24/7 right now since I'm off for the summer from teaching. I'm happy to help out with your pets during the week. I live in a pet friendly area with plenty of room to walk. I have 1 cat who is used to other cats and dogs.
About: I’ve always loved caring for pets and I truly love treating them like family. From playtime and long walks to snuggles and mealtime, I make sure every pet feels happy, safe, and loved while their owners are away. My current schedule allows for a lot of flexibility, so I’m able to provide immediate personalized care for your pet whenever that time comes. When I’m not home with my furry friends, I’m happy to help out with yours! I have a fenced in backyard and am able to provide a safe and calm environment. When caring and visiting your furry friend, I am happy to fulfill all instructions and details so that you have peace of mind and know that they are in the hands of someone who truly cares about them as much as you do.
Over 4 pet parents in Winterset have booked house sitting
How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Winterset is $45
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 house 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.
Sitters in Winterset average 5 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winterset on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 396 house sitters in Winterset. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 92% of Winterset house sitters respond in under an hour.
House sitters in Winterset have an average of 14 years of experience. House sitters with repeat customers have an average of 5 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winterset.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winterset house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.




