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Top rated Winsted house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“My puppy had abdominal surgery and required more care than usual - more potty breaks, more feed times, meds given several times, including eye drops! Ashley did a great job taking care of him throughout the day and overnight! Would recommend”

“Karri was great with our elderly dog while we were gone for a week. She stayed in our home and took care of him like he was her own. She went over and above in taking care of Ben. He has ongoing health issues that can change very quickly and she easily adapted to his needs, gave meds and even completed ear cleanings when needed. I would recommend her to anyone looking for a dog sitter. We will not hesitate to have Karri stay with Ben again.”

“Allysa did a wonderful job with my girls. She sent me pictures and was great at communicating things. She would reach out with questions. My girls were so happy to be able to stay at home while I went to a family wedding. I would highly recommend her and I will use her again!!!”

About: I currently have 2 cats of my own that I take care of, and I also have experience with cat-sitting, dog-sitting, dog-walking, and more 🐱🐶❤️ I’m working part-time as a pet sitter right now and I can watch your pets on any day of the week (including weekends) from 3:30pm to midnight, but I am willing to make exceptions if I receive any inquiries for pet-sitting outside of my normal hours :) I mainly care for pets at the homes of my clients, but cats are welcome in my home if they don’t mind the company of my 2 cats :) 1 cat per day, and you have to bring your cat in some type of cage/crate. They will be staying upstairs where my room, litter box, and food/water bowls are located.
“Gabby was incredible! Our older dog and our skittish dog were both so happy with her. The cat didn’t even scold us when we returned like he usually does. We received regular updates and photos throughout the week and when we got home, the house was neat and tidy. We will absolutely ask Gabby back to housesit and watch our “outlaws” again. We can’t possibly recommend her enough!!”

About: I have always lived with a cat. Every friend I have has either a cat or dog or more. I have had exotic animals as well. From breaded dragons to praying mantis. First thing I do make sure to feed everyone. Moving the cat bowls back down because the dog likes to try to eat them at night. The dog gets walked before she eats. We just bought a walkway to help our aging cats reach the food bowls. We have three separate feeding areas. So that everyone can eat. One of our cats has anxiety. We have gone through various methods until we find the one that works to relax her.
About: I’ve had and loved animals my entire life. As an adult I’ve had 2 German shepherd’s and have done positive reinforcement training with both of them. My daughter also had a rescue dog that was very special to our family. Currently I have 3!! dogs and a cat. I love all furry friends! My availability to provide pet care varies. I’m currently working full time as a nurse/clinic leader but I have the flexibility to work from home on occasion. I’ll do my best to accommodate needs. I can provide and respect any safety recommendations as requested. I want you and your pet to feel as comfortable as possible while you’re away.
About: Hi there! I’m Kelsey — a Certified Veterinary Technician, full-time animal lover, and proud cat mom of six. My husband Rick and I live in Cokato, Minnesota, where our home is happily ruled by a crew of whiskers, purrs, and wildly different personalities. We share our lives with six cats, each with their own quirks and needs — from the confidently social to the quietly anxious, from the senior who needs meds to the youngster with endless curiosity. Living with such a diverse feline family has shaped the way I approach every pet I meet: with patience, kindness, flexibility, and a genuine desire to understand who they are as individuals. As a Certified Veterinary Technician, I bring several years of hands-on clinical experience with dogs, cats, and pets who need extra medical support. I’m very comfortable giving medications, supporting chronic illness care, monitoring behavior changes, and handling pets who may be shy, nervous, or slow to trust. Special-needs pets hold a big piece of my heart — I know how important experienced, gentle care can be. I’m also building my confidence with exotics and pocket pets, and I’m always excited to learn about new species, routines, and little personalities. If your pet scurries, hops, slithers, or squeaks, I’m happy to meet them! Because of my own busy furry household, I’m not able to accommodate pets in my home — but I am more than happy to stay in your home, where your pets feel safest and most comfortable. Keeping their routine familiar helps them relax, and it lets me give them the kind of attentive, stress-free care they deserve. And you don’t need to be heading out of town to reach out! I’m available for daily walks, drop-ins, and companionship visits anytime your pet needs a little extra attention, exercise, or love throughout the week. Whether it’s a lunchtime walk, a play session to burn off energy, or a comfort check for an anxious pet, I’m here to help their day run smoothly. When I’m with your pet, they get the full package: – Warm, compassionate care from someone who treats them like family – Professional experience that gives you peace of mind – Lots of updates, photos, and notes so you always know how they’re doing – Playtime, snuggles, enrichment, and patience, tailored to their personality My goal is simple: to make your time away easier — and your pet’s time with me joyful, safe, and comfortable. If you’re looking for a sitter who truly understands animals inside and out — medically, emotionally, and behaviorally — I’d love to meet you and your furry (or feathery or scaly!) crew. 🐾💛 I currently work part-time at a veterinary clinic, usually around two days a week. The exact days vary from week to week, and I typically receive my schedule the week prior. Because of this, my availability can shift — but I’m always happy to coordinate and work with you to find the best times for visits or extended care. The rest of my week is dedicated to pet sitting, which gives me plenty of flexibility for daily check-ins, longer stays, and multi-visit days. Whether you have a friendly dog, a cozy-at-heart cat, or a unique companion with feathers, scales, or tiny paws, I provide care right in your home where your pet feels safest. Familiar surroundings help reduce stress, and my goal is to keep their routine steady and their world feeling normal — whether I’m popping in for a quick visit or staying through a longer trip. For short pop-ins, I focus on exactly what your pet needs in that moment: walks, meals, medications, litter scooping, enrichment, or just some comforting company to break up their day. For extended stays, I follow their routine closely — feeding, exercise, playtime, quiet time, and any medical care they require. I adjust my approach to each individual personality, from confident and social to shy, nervous, or slow to warm up. No matter the species or temperament, your pet will always receive gentle, attentive care and plenty of updates so you feel connected while you’re away.
“Samantha took excellent care of our dog and home, including going above and beyond by clearing our walks post snowstorm. We have a high-energy, playful, and sometimes demanding dog, and it was clear Samantha knew what she was doing. Ziggy loved her! We really appreciated getting the daily updates and photos.”

“Autumn was amazing with out 2 English setters- she handled medications wonderfully and gave them so much attention and walks! Our neighbor even commented on how great she was. Look forward to using her again!”


About: Hello, Pet Parents. My name is Cory, and I'm going to tell you a bit about myself! I've always been involved with animals in my life and have had many pets! I've had 3 dogs, mice, hamsters, and even a frog! Not only have I had pets, but I've had past experiences with pets and pet owners, and here are some as follows! ————————————————————— Experience: Worked for an adoption center where I took care of dogs and cats. Dog walking Pet sitting Many animal based classes Currently working at a board and train facility Training/Fostering a soon to be police dog that will be stationed at a middle school and helping with tracking cases ————————————————————— If you have any questions please don't hesitate to ask! I'm currently working part time so I'll have plenty of time to take care of your fuzzy little friends whenever needed! I'll always talk to you about openings in my schedule that fit with yours! I have a couple pets, a Sheprador which is a German Shepherd and Labrador mix named George, and a hamster named Baba. I feed my dog George twice a day making sure to let him outside right after, I regularly brush him because he just doesn't stop shedding, I wash him every other month so he doesn't get stinky, give him all of his medication for his allergies, and just giving him constant attention such as walks! Baba gets fed once a day with a healthy balance of veggies, fruits, seeds, and original food. I clean his cage every 1 to 2 weeks depending how it looks and/or if it stinks, and finally I regularly take him out of his cage to pet him and let him run around in his ball! George and Baba get along haha! Plus a new member being Chunk a little lab puppy!
About: Love all doggies every shape and size! Grew up with two beautiful west highland terriers who were the best birthday gift in the world for 10 year old me. Been dog sitting/ house sitting for my family and friends for quite some time now and thought I should start doing it more so here I am! I work a few jobs (some part time other seasonal work) super grateful that my jobs are extremely flexible and so fitting in dog care and dog sitting is easy and attainable. I’m very attentive when it comes to understanding and learning owners routines and schedules they have for their furry friends. Feeding times, what the dog likes and dislikes, how many times they need to be let outside etc. I’m always alert and aware if anything goes astray.
“Nakita was the best! I had major anxiety about leaving my two dogs for the first time - to the point where I’ve hardly left the house in two years, let alone go on a much-needed vacation! Nakita was both professional and personable, which made it an easy choice to hire her and feel confident about leaving my babies with her. She sent me daily updates with super cute videos and photos, which made it easier for me to be away and enjoy my travels. I have a quirky, anxious older dog (Gus) and a rescue with major stranger-danger (Grace), and Nakita handled both of their personalities like a champ. It was only a matter of time before my shy girl Grace was begging her for pets and attention. Her experience in working with animals with special needs really shines. She also made sure to give them their medications on schedule. I would definitely hire her again!”

“Kayla was amazing with our Phoebe girl! She checked in often with updates, and we were able to enjoy a worry free vacation. Our skittish dog is easily stressed, but we were sent pictures of her snuggling, having fun and loving her new friend!”

About: I’ve taken care of dogs since I was about 15 years old and have one of my own. Ready to play with and take care of your furry friend! I currently work 3 days per week, so my schedule is open and free the other 4 days! Reach out with any questions about availability. I have a fenced in large backyard and one playful dog of my own to keep your dog company. Safety and comfort are always important to me!
“Alex did an amazing job with our critters! She was very communicative, sending frequent updates and fun photos and videos. I felt so reassured the pets were having a great time and were well cared for. She went above and beyond her expected duties. We will absolutely ask her to petsit again!”

“Oksana did a great job caring for our 1 year old puppy. Layla is a high energy dog but Oksana managed to find activities to tire her out each day and give her lots of love! We definitely recommend Oksana for taking care of your furry friends.”

About: I currently do not have an animals , but I have 10 years of experience and treat any animal in my care as if they are my own I work full time as a nurse I am available once a week and every other weekend for full time care for your furry companion Fenced in yard , can offer potty breaks every hour , go for walks clean up dog poo etc , go for runs , give them a bath if needed
About: I’ve had a dog in my household for as long as I can remember! My family has had golden retrievers throughout my life, and my brother currently has an adorable golden puppy. Unfortunately I can’t currently have a pet as I’m just graduated from college, so dog sitting or walking will help fulfill my love for dogs! I just graduated this May with my masters degree from St Cloud State University and have just recently moved to this area. I will not be starting my new job until next school year and therefore I’m available for pet care any day of the week, and would have a flexible schedule for dog sitting or walking. Dog walking would be great for my routine as I’m an early riser and would be happy for an early morning stroll! I’m unable to provide services in my home as I am currently in an apartment, however I’m open to caring for your pet in any environment provided. I’ve had experience living with a large dog most of my life, and have been with them through all stages of their lives. I’m currently taking the summer off so I am looking to pet care for something fun to do in all of my newfound free time! I am willing to adapt to any of your pets needs in and around your home. Whether that be long walks or curling up on the couch together, I am willing to do whatever they need to feel comfortable away from their owners.
Over 3 pet parents in Winsted have booked house sitting
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1. Search
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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
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The median cost per night for house sitting in Winsted 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 Winsted average 4 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 Winsted on Rover as of Feb 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 Feb 2026, there are 125 house sitters in Winsted. 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, 84% of Winsted house sitters respond in under an hour.
House sitters in Winsted have an average of 17 years of experience. House sitters with repeat customers have an average of 4 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 Winsted.
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. Winsted 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.

