House Sitting Winsor Hills
Find a loving house sitter to watch over your pets and your home.

Over 13 pet parents in Winsor Hills have booked house sitting
Winsor Hills, 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.
“Sierra did a great job dogsitting my senior dog and housesitting while I was out of town for a long weekend! She sent updates and pictures, which was very reassuring!”
“Micah did a fantastic job with our pets and home! We received regular updates and photos and we came back to happy pets and a spotless home. Would highly recommend her to anyone looking for a sitter!”

“There are not enough stars in the universe to give Bria! We have 4 dogs. They’re a lot of work and all need different things. Bria was fabulous and spent all day with them. She made sure the dogs were walked, fed and spent time with each one individually. She took them out for that, oh so important last poop too. 🖤🌻”

“Tabitha is WONDERFUL! My dog is very emotionally needy (has anxiety), and I needed a sitter very last minute. Tabitha came to the rescue and was so attentive with Franny and did such a good job with her! I really trust her and i can’t wait to use her again 🙂”

“Great care for our little rescue guy. My dog instantly took to her. Eileen house sat and dog sat and was beyond responsible for both. We would 100 % call her when needed. She went out of hr way and I knew my guy was safe and happy.”

“Shania has helped me out and taken great care of Gizmo, but none so much as this week. I was on vacation and we received an epic amount of snow and freezing temperatures. She encouraged Gizmo to eat when he was refusing, had to deal with Inside accidents because he refused to go outside, and walked him in many short bursts so he didn’t get dangerously cold. What a freaking rock star. If you’re not booking her then what are you even doing?”

“I came home to happy and healthy dogs! Although they are normally anxious and nervous about new people, Kevin connected with my two dogs very quickly during our meet and greet, easing my own nerves. He communicated throughout the sit and I was grateful to always get a quick response when needed. Highly recommend and I will be rebooking him for sure!”

“Aleya was AMAZING! She took excellent care of my dog, sent a lot of pictures, she’s great at communicating everything and she’s a very happy person! Will definitely book her again!!”

“Emily was amazing, my boys loved her, and I felt very comfortable leaving them in her care. She was professional and very communicative, the daily photos helped so much. Even when encountering some unexpected issues (on my end) and with Atticus boycotting his meds, she handled them with grace and went above and beyond. I could not recommend Emily enough!”

“Demi was really great watching my cat for a few days! She was very communicative throughout the housesitting stay and sent me daily, adorable pictures/ videos of my cat. I could tell my cat was happy and relaxed each day which is not typical while I’m away. I will definitely ask Demi to cat sit again in the future!”

“Emily is great! She sent continual updates and pictures throughout her time house sitting. It was clear that besides regular walks she also spent lots of time hanging out and cuddling with my dog, who is very affectionate and needs the attention. Would definitely book again!”


“I had the pleasure of working with Robyn as my dog walker/dog sitter. From day one, it was clear that Robyn had a genuine love and passion for dogs. Her professionalism and reliability were outstanding. I always knew I could count on her to be on time and take great care of my furry friend. Not only did she ensure my dog got plenty of exercise and fresh air, but she also provided the companionship and attention that my babies need. She made sure to always send daily updates and pictures! What sets Robyn apart is her deep understanding of canine behavior. She knew just how to handle my dog’s personality and needs, making every walk a positive experience. She made sure to ask me about training and what she can do to follow our usual routine as closely as possible. My dogs absolutely adored Robyn and were always excited to see her. Safety was a top priority for Robyn as well. I appreciated the thoroughness in making sure my dog was secure during walks, especially when crossing streets or encountering other dogs. Her attention to detail gave me peace of mind. I can’t recommend Robyn highly enough. She provided exceptional care, trustworthiness, and genuine affection for my pet. If you want a dog walker who goes above and beyond, Robyn is the one to choose. My pups and I are truly grateful for her wonderful service and will be recommending her to family and friends.”

“We had a wonderful, stress-free experience with Samantha during her week-long stay in our home. She took great care of our dog and he was completely himself when we returned. Our home was also well cared for and very clean when we returned. She kept us updated regularly with photos and messages, and we had peace of mind while traveling. Samantha is reliable, trustworthy, friendly, and professional. We would absolutely book her again!”

“Keira was great with our old pup Toby while we were out of town. She was knowledgeable about care and Toby was in great hands. She gave updates and photos throughout the stay.”

“Ashley was scheduled to watch our three cats for three nights, but our plans suddenly went awry and she stepped in to save our bacon and extend her stay. She went above and beyond to make sure the house was ready for the sitter who would come after her, including washing linens. We were abroad when all this happened, so it was an immense relief to have someone considerate and reliable taking care of things. And our kitties were all in good nick when we returned! We would definitely call on her again.”

“Cashae was a wonderful sitter for our 2 pups!! She is a Dog Lover for sure! She took great care of our dogs. She was with the dogs 24/7. It meant a lot to me knowing that Cashae was a perfect fit as a dog mom, while we were gone for awhile...I highly recommend Cashae!!?”

About: I’ve always had a special place in my heart for animals! I’ve grown up with lots of cats, dogs & more! I currently work at my local animal shelter as a Behavior trainer, and I treat all of the fur babies as if they were my own until they get their furever home. I care about each of them and only wanna make them feel love special and cared for! Since I'm working part-time right now, I have plenty of open time to dedicate to your fur baby. Pet care fits easily into my daily routine. My days are flexible, so I can give your pup my full attention - whether that's a nice long walk, playing fetch at the park, doing food puzzles for mental enrichment, or just hanging out for lots of love and pets while they enjoy a bone. I'm happy to stick to whatever routine makes them most comfortable. As the owner of a 1.5-year-old rescued Doberman mix, I understand how much care, exercise, and enrichment dogs need to thrive. My boy gets daily physical exercise plus mental stimulation through enrichment, puzzle toys, and Kongs. I bring that same standard of care to every pet I watch - just let me know your pet's routine and needs, and I will follow it to the T. As for Safety is always my #1 priority - whether we’re out and about in town or on a quiet hike in the woods.
“Asia took care of our dog Luna over a long weekend trip. Lu is ~10 years old and has various quirks that go along with that, Asia was patient and caring with her. She administered her medication, followed our instructions, and sent us several updates. Asia was also very responsive and respectful of our home. I would recommend Asia as a pet sitter for anyone.”
The median cost per night for house sitting in Winsor Hills is $50
Pet parents share their Rover experiences - Winsor Hills
Kaitlin was absolutely wonderful! From the beginning to end we felt comfortable that our dogs and house were well looked after while we were away. She even took incredible action photos that really captured special moments. Couldn’t ask for a better pet sitter! I plan to book her again soon for our next trip!

Ashley could not have been more amazing! She came for a meeting and great visit prior to dogs sitting for us, and immediately showed great skill and warmth in her interactions with our dogs. She took fantastic care of our house, and I felt completely safe and comfortable, knowing that our home and pets would be in good hands. I cannot recommend her highly enough.

There are not enough stars in the universe to give Bria! We have 4 dogs. They’re a lot of work and all need different things. Bria was fabulous and spent all day with them. She made sure the dogs were walked, fed and spent time with each one individually. She took them out for that, oh so important last poop too. 🖤🌻

Kevin was excellent! He stayed in our home while caring for our dogs, and we couldn't have asked for a better sitter. He was respectful of our home, left everything clean and in great condition, and took wonderful care of our pups. His communication was excellent throughout our trip, giving us peace of mind while we were away. We came home to two happy dogs and a well-cared-for house. We'd absolutely book Kevin again and highly recommend him to anyone looking for a reliable, trustworthy house sitter!

Julion was an amazing dog sitter! He took incredible care of our dog, Chance, our big 115-pound pup, while we were away. He was very attentive and even made sure to be mindful of the heat and hot pavement during walks, which we really appreciated. He sent us daily updates with lots of pictures, giving us complete peace of mind and letting us see how happy Chance was throughout our trip. When we got home, the house was spotless and exactly as we left it. It’s clear that Julion is responsible, trustworthy, and genuinely cares about both the pets and the homes he looks after. We would absolutely book Julion again and highly recommend him to anyone looking for a reliable, thoughtful, and caring dog sitter!

We were very happy with Sean as a pet sitter for Bruno, our American Staffordshire Terrier, who is very anxious with new people. Sean's patience and understanding helped Bruno relax quickly. Sean sent daily updates and photos of Bruno playing in the yard and chilling on the couch. Sean also finished giving Bruno the final doses of medication for an UTI developed just before our vacation. We will definitely use Sean in the future.

Trust them completely with our pups and our home. We have a two dog home that includes a senior dog who has mobility issues and medication needs. They’ve never had more exceptional care and are always happy and content when we arrive back home. Same goes for the house. House is clean and always well taken care of. My wife and I even came home to all our mail collected and our recycling put to the curb ❤️

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?
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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.
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