House Sitting in Winfield Hill
Find a loving dog sitter to watch your dog overnight in your home.

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winfield Hill house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Baylee was the perfect sitter for my pup while I had to run out of town. She sent cute pictures and videos and communicated really well! I definitely plan to use Baylee the next time I need a sitter.”

“Gwen is the best! Our dogs love her. They are so joyful when she is with them. Gwen has dog sat for us twice and both times we were able to relax and enjoy our vacation knowing that our fur-babies were in good hands. We highly recommend Gwen. ❤️”

“Hannah was great, we did a meet and greet the week before and went through the routine. My dogs really liked Hannah and I was happy they felt comfortable with her. While I was away she sent photos of my dogs and kept me updated on how they were doing. My little one does not like fireworks and I was grateful to have her keeping a close eye on him. I would recommend Hannah to anyone and I would work with her again. Thanks Hannah for helping out on the 4th of July weekend!”

About: I’ve taken care of dogs and cats for my family for about a year now, and I’ve been wanting to walk dogs for a while now, and I believe I’m the best choice for your needs. I am currently on summer break, so I’ll have plenty of time to spend with you animals! I am available any day of the week from 7am-9PM. I live in a house with a fenced in yard that my cat loves to play in. He loves to go on rides weekly. I also clean out his litter box daily.
“Grateful that Tyeshia and her brother were able to take Wooli last minute. Although I wish we had received photos/updates while we were gone, we picked up our happy and healthy dog at the end of the day, which is all I really care about.”


“Kyara was a wonderful sitter to my 3 dogs. She stayed in our home for the days we were gone and left it in perfect condition. She sent updates each day about how they were doing. She was able to care for my senior dog who needed medication. Thank you for watching over our dogs!”


About: I’ve taken care of all kinds of “family members” over the years. From young to older, rowdy to anxious, bitty ones to large lap lovers. I’m familiar with administering medications, addressing litter boxes, special eating needs and am well versed in sleeping arrangements. I treat every member with love and care as I would my own. I currently work from home where I am able to travel and be present during the day and evening. I can do walks during my lunch hour to ensure they’re not stuck inside all day or whatever their needs are. Though it is a wfh I have a schedule, but I always make it work for the pets needs. I will do everything necessary to keep the fur babies safe and secure. I’m able to place them in crates or rooms if necessary or continue with crate training or house training if they’re in the middle of learning.

“Jasmine did a great job with our dogs and was very communicative with pictures and updates! She also took great care of the home! It was just as we left it. Even when my golden retriever pulled out some of my personal belongings she respectfully put them back. I would consider Jasmine very responsible and she has great character; it was also extremely nice to meet her because she was exceptionally pleasant and kind.Thanks again, Jasmine”

“Jen was awesome!! She house sat for 5 days and followed the schedule I left for my two fur babies. Both dogs are large dogs and she walked them every day without hesitation! They were happy and very well taken care of. I was able to relax and not worry because Jen would send text and pictures daily letting me know what was going on. I will definitely be using her again. Thanks Jen!”

“A top-notch caregiver for my two kitties and I have worked with many sitters in the past 10 years. I chose Asha because she has experience with special needs pets. She was willing to house sit with my babies so that she could express the bladder of my special needs girl. She fed, watered, brushed, loved and expressed the bladder of my little one every 6 hours to keep her on schedule day and night. If you are hesitant about traveling because of your fur babies, call Asha. She is delightful, willing, clean, communicative and observant. She will care for your home and your pets as her own. There are not enough stars for me to recommend Asha highly enough! She is a personable, professional, and experienced lover of animals… I have already talked with her about future sits. She is the answer to my prayers and my babies love her!”

“Meaghan was great! Our dogs absolutely loved her and had a great time during our absence. She was timely, communicative, and had no issues with our anxious pups and their many needs. We can’t recommend her enough and will absolutely rebook with her!”

About: i’ve been around animals my entire life i have 5 dogs and two cats and i am also in vet school. i worked at several boarding facilities and love it i have a lot of free time since i’m doing class online so i can spend the whole day with any animal! i also get my dogs out of the house and take them to the park i have two dogs at home and a fenced yard for my animals my animals are always around other dogs they love other animals and are very hyper sometimes

About: Looking for a calm, dependable, and experienced sitter for your beloved pet? You've found her. I bring a blend of professionalism and genuine affection to every pet I care for. Whether it's daily walks, cozy cuddles, or administering medication, I handle all with a gentle touch and keen eye. Your pet's comfort and well-being are my absolute priority, ensuring you have peace of mind knowing they're in capable hands. I work in San Jose full-time in a 8 a.m.-5 p.m. Monday thru Friday job. My hours can be flexible when given advance notice. I also have my own transportation, and am willing to drive within a reasonable distance on the bay area. Extra open to offers that include mileage of over 20 miles from me. I do have a 9 year old old cat who mostly keeps to themselves, but is wary of aggressive animals. . As of now I do not board pets. Sorry.
“Caleb was so kind and thorough. He kept everything clean, made sure my pup got his pills, and gave us plenty of updates. I have a stranger-shy pup, and Caleb worked with us to make it all work out wonderfully. I will definitely be using him again.”

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 Winfield Hill is $40
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 Winfield Hill 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 Winfield Hill on Rover as of Jun 2026 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 Jun 2026, there are 267 house sitters in Winfield Hill. 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, 89% of Winfield Hill house sitters respond in under an hour.
House sitters in Winfield Hill have an average of 14 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 Winfield Hill.
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. Winfield Hill 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.





