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Top rated Winston house sitters
“Nora was excellent. She took great care of the house along with my dog and cats. Was communicative and sent pictures. I would highly recommend!”
“Taylor did a great job house sitting for us and we will definitely re-book with her! It gave us such peace of mind knowing she was there with the dogs. She was so detailed oriented and made sure everything was as we asked.”
“Laci did a great job taking care of our 2 energetic springer spaniels (Willey is energetic+) She spent 2 days with them in our home. She followed all directions we left for her and checked in with us periodically - including pictures. We have had the same sitter for 7 years so we were somewhat nervous trusting the "kids" to someone new. Laci was a great choice! I will not hesitate to book her again and recommend her to my friends!”
About: I have loved animals my whole life. I’ve had animals around since I was in diapers. I rescue them to this day! I have three rescues in my home and I provide top notch care, just read my reviews. I treat everyone’s pets as my own. I’d be happy to care for your furry friends Anyday!!! I’m a stay at home mother of a two year old boy. I have plenty of free time to take care of my home and animals and your animals too! It would be easier for everyone for me to watch your pets in MY home or do drop ins at your place. I have a separate area for cats. My dogs typically roam upstairs and the cats play downstairs in their own little sanctuary. I like to make sure every one is comfortable <3 I have a large yard for dogs to run around in and a small dog run area that’s fenced in. I’m open to keeping your dogs inside my home that way I can keep a good eye on them but if they want to hang out in the yard that’s fine too. I do enjoy going to the dog park so if that’s okay with YOU then I’m open to that which is right around the corner from my house (lucky me:) I’m very experienced with use of kennels for training too. I have a lot of experience with all animals and that gentle nature they’re attracted to.
“Alisha took wonderful care of our precious girls (a cat & a dog - little girls who are rather high maintenance 😊), and our home. She is extremely knowledgeable and experienced, and she provides excellent care! We will definitely be utilizing Alisha's services in the future when we plan trips away from home!”
“We have used Joshua 3 or 4 times he loves our dogs and makes them happy, and of course that makes us happy: they love him and because we keep booking him, their anxiety when we leave has gone way down. Joshua makes our lives easier because he takes such good care of our 4 legged boys.”
“We have used Jessica to house sit with our dog the last few times we were out of town. This time our flights were delayed an entire day and she was able to help us and stay another night to make sure our dog was cared for. Highly recommend her services!”
“Nia did a fantastic job with our 4 girls! A few of them are higher energy so it can get pretty crazy at times, but she handled it all easily. She was super flexible and willing to work with us to make the whole process as convenient as possible. Highly recommend!”
“Holly was incredible our not so friendly dog loved her! She was so good with Winter. Holly was also such a sweet person!! I would use her services a million times!!”
“HIRE CHRIS. I won the lottery with him. It was my first time using Rover. I have a special needs rabbit who needed a caretaker after a rabbit boarding service was no longer available. I messaged several sitters and Chris was the first to respond. He is responsive and communicative. What I absolutely love about Chris, among many things, is that he asks questions. Not in a "what do I do" kind of way. Rather, "how do I do this to make sure it's done correctly". My special needs rabbit is on a specialized diet. I left Chris with instructions, which he followed to a tee, but he also sent a photo of the food. (My rabbit is feed very soft, watered down pellets and Critical Care due to recent dental surgery). I'm happy that he did because my rabbit can't chew on pellets. He sent lots of photos of Moo, too. Chris was also flexible with the initial meet 'n' greet appointment and visiting my landlord's office to pick up my front door key (which has to be loaned out). One of the reasons I chose Chris was his close proximity to my apartment. I will 5000% hire Chris again for my rabbit sitting needs. He took great care of my very special needs rabbit and Moo liked him too! I recommend him for your pet sitting needs, including small mammals!”
“Brianna was absolutely amazing! She was very responsive, caring, and sent lots of photos :) looking forward to booking with her again soon.”
“Heather was very responsive. She kept the pets alive and happy, and the pets obviously liked her.”
“Whitney did a great job watching our dog and cat this past weekend. Both pets were happy and the house was in great shape! I would highly recommend Whitney! -Jenni”
About: I have had a dog my entire life. I have worked as a dog bather in the past for 8 plus years. I get alone with all dogs and make friends with everyone I meet. I like to get to know and meet all new dog family members. I watch family members dogs often when they go out of town. I am free everyday to take care of anyone dog that needs care and love. Right now I’m available anytime needed just not at night when I might be asleep I take my own dog for a walk everyday around the neighborhood. I bath him once a week and love playing with him and his toys outside getting all the energy out of him till he ready for a good nap
About: I’ve been around and taken care of dogs since I was young, All sizes from larger breeds to little dachshunds. I absolutely love it and it’d be amazing if I could make my love for dogs a career. My schedule is wide open—I’m available to walk your pup almost anytime! Flexible, reliable, and ready when you need me. Let’s get those tails wagging! I am willing to care for your furry friend in your home. If you have any details about your fur-baby you need to add, any special medications, etc. Always let me know.
“Sierra was amazing! We came to her in a rushed panic when our original dog sitter had backed out 12 hours before we were going away for a week. Sierra was super accommodating and picked up our dog and dropped her back off so when we arrived at home, our dog would be waiting for us. She sent us photos and recaps every day! Our dog Netty had a smile in every photo lol! We will DEFINITELY use her again!!”
About: Hello, my name is Samantha! I am willing to open my home to your babies or take care of them from the comfort of their own home! From overnights to a 20 minute walk, I am looking to help pet parents in need! I have experience with my own pups and dog sat for many others throughout the last 8 years. If watching at my home your fur baby will have two playful buddies and a giant yard to run around in! I love to watch dogs adventure and enjoy life at the lake so I would love the opportunity to do that for your fur baby. My favorite walking spot is Devils Lake and I always have a pocket full of treats to reward good behavior!
About: I’ve had dogs and cats my whole life. Family and friends have relied on me to walk and feed their pets. I’ve cared for cats and dogs of all ages! I’m currently working part-time as a cashier. So I would be available most nights and Saturdays. I am always looking forwarded to hanging out with furry friends. I respect all clients homes and you won’t even tell I was there. I care for our furry friend and clean up after them and myself!
About: With a spacious lakefront property, I provide endless walks, frequent potty breaks, and serene relaxation spots, ensuring your pets enjoy a blissful, loving care experience. Retired and pet free, I’ll dedicate my days to your fur babies, offering long walks, play, and snuggles by the lake, ensuring their happiness is my top prioroty. In my home or yours, I provide attentive, personalized care tailored to each pet’s needs, from engaging play sessions to soothing snuggles, ensuring a comfortable, joyful environment.
About: Throughout my 8 years of higher education, I worked with children and pets to make money. I’ve nannied for multiple families, who had pets of all kinds. I’ve dog sat for 6 families which included the typical feeding, walking, playing, and bathing. I am currently studying for my board examination, leaving me with a flexible schedule. I don’t have any current day to day commitments, which makes it easy to accommodate your needs. I will follow what you think is best for your pet. You know your pet best! Of course, I’ll always follow general safety guidelines and will keep a close eye on your pet.
Loving house sitters in your neighborhood
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Nora S.Star Sitter
“Nora was excellent. She took great care of the house along with my dog and cats. Was communicative and sent pictures. I would highly recommend!”
taylor m.
“Taylor did a great job house sitting for us and we will definitely re-book with her! It gave us such peace of mind knowing she was there with the dogs. She was so detailed oriented and made sure everything was as we asked.”
Laci R.
“Laci did a great job taking care of our 2 energetic springer spaniels (Willey is energetic+) She spent 2 days with them in our home. She followed all directions we left for her and checked in with us periodically - including pictures. We have had the same sitter for 7 years so we were somewhat nervous trusting the "kids" to someone new. Laci was a great choice! I will not hesitate to book her again and recommend her to my friends!”
Kimberly S.Star Sitter
“Kimberly is not only a mother to her children but also to her dog children. While caring for my doggies Lyla and Tiny, I knew they were in great hands, even when my dogs can be naughty at times. Kimberly provides attention, love and caring support to all humans and animals!”
Alisha J.
“Alisha took wonderful care of our precious girls (a cat & a dog - little girls who are rather high maintenance 😊), and our home. She is extremely knowledgeable and experienced, and she provides excellent care! We will definitely be utilizing Alisha's services in the future when we plan trips away from home!”
Joshua W.
“We have used Joshua 3 or 4 times he loves our dogs and makes them happy, and of course that makes us happy: they love him and because we keep booking him, their anxiety when we leave has gone way down. Joshua makes our lives easier because he takes such good care of our 4 legged boys.”
Jessica S.
“We have used Jessica to house sit with our dog the last few times we were out of town. This time our flights were delayed an entire day and she was able to help us and stay another night to make sure our dog was cared for. Highly recommend her services!”
Nia G.
“Nia did a fantastic job with our 4 girls! A few of them are higher energy so it can get pretty crazy at times, but she handled it all easily. She was super flexible and willing to work with us to make the whole process as convenient as possible. Highly recommend!”
Holly A.
“Holly was incredible our not so friendly dog loved her! She was so good with Winter. Holly was also such a sweet person!! I would use her services a million times!!”
Chris F.
“HIRE CHRIS. I won the lottery with him. It was my first time using Rover. I have a special needs rabbit who needed a caretaker after a rabbit boarding service was no longer available. I messaged several sitters and Chris was the first to respond. He is responsive and communicative. What I absolutely love about Chris, among many things, is that he asks questions. Not in a "what do I do" kind of way. Rather, "how do I do this to make sure it's done correctly". My special needs rabbit is on a specialized diet. I left Chris with instructions, which he followed to a tee, but he also sent a photo of the food. (My rabbit is feed very soft, watered down pellets and Critical Care due to recent dental surgery). I'm happy that he did because my rabbit can't chew on pellets. He sent lots of photos of Moo, too. Chris was also flexible with the initial meet 'n' greet appointment and visiting my landlord's office to pick up my front door key (which has to be loaned out). One of the reasons I chose Chris was his close proximity to my apartment. I will 5000% hire Chris again for my rabbit sitting needs. He took great care of my very special needs rabbit and Moo liked him too! I recommend him for your pet sitting needs, including small mammals!”
Brianna J.
“Brianna was absolutely amazing! She was very responsive, caring, and sent lots of photos :) looking forward to booking with her again soon.”
Heather C.
“Heather was very responsive. She kept the pets alive and happy, and the pets obviously liked her.”
Whitney W.
“Whitney did a great job watching our dog and cat this past weekend. Both pets were happy and the house was in great shape! I would highly recommend Whitney! -Jenni”
Austin P.
“Austin watched our 1 year old mini-Aussie on short notice. Frankie was well taken care of with walks, playtime and snuggles. Will definitely be calling Austin again to watch Frankie❣️”
Shannan L.
About: I’ve been around and taken care of dogs since I was young, All sizes from larger breeds to little dachshunds. I absolutely love it and it’d be amazing if I could make my love for dogs a career. My schedule is wide open—I’m available to walk your pup almost anytime! Flexible, reliable, and ready when you need me. Let’s get those tails wagging! I am willing to care for your furry friend in your home. If you have any details about your fur-baby you need to add, any special medications, etc. Always let me know.
Sierra J.
“Sierra was amazing! We came to her in a rushed panic when our original dog sitter had backed out 12 hours before we were going away for a week. Sierra was super accommodating and picked up our dog and dropped her back off so when we arrived at home, our dog would be waiting for us. She sent us photos and recaps every day! Our dog Netty had a smile in every photo lol! We will DEFINITELY use her again!!”
Samantha G.
“Samantha watched my dogs for many years before moving to Baraboo. She loved taking them for walks and getting to know their personalities! I would definitely recommend her to watch other pups at her house which has a huge yard and two lovable fur friends to play with!”
Cheyenne M.
About: I’ve had dogs and cats my whole life. Family and friends have relied on me to walk and feed their pets. I’ve cared for cats and dogs of all ages! I’m currently working part-time as a cashier. So I would be available most nights and Saturdays. I am always looking forwarded to hanging out with furry friends. I respect all clients homes and you won’t even tell I was there. I care for our furry friend and clean up after them and myself!
Anthony R.
“I have known Tony as a highly engaging pet owner and caregiver. He takes the time to connect with all pets he encounters and they always greet him as their best friend. Tony is a highly trustworthy person that will go the extra mile to make your pet feel safe and well cared for.”
Hannah F.
About: Throughout my 8 years of higher education, I worked with children and pets to make money. I’ve nannied for multiple families, who had pets of all kinds. I’ve dog sat for 6 families which included the typical feeding, walking, playing, and bathing. I am currently studying for my board examination, leaving me with a flexible schedule. I don’t have any current day to day commitments, which makes it easy to accommodate your needs. I will follow what you think is best for your pet. You know your pet best! Of course, I’ll always follow general safety guidelines and will keep a close eye on your pet.
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!
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.
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 Winston on Rover as of Aug 2025 was about $40 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 Aug 2025, there are 51 house sitters in Winston. 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, 78% of Winston house sitters respond in under an hour.
House sitters with repeat customers have an average of 3 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 Winston.
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. Winston 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.
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