House Sitting Winfield Hill
Find a loving dog sitter to watch your dog overnight in your home.
Winfield Hill, 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.
“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. ❤️”
About: Dogs have always been apart of my life. I have had many different breeds throughout my life. Taking care of dogs are my passion and I hope you choose me to help you out. I am currently doing online classes until July 13th so I will be available for drop-ins 3 times a day and walks 3 times a day. After that I can drop in however often is needed, as reasonable. I am not offering boarding services but I am available to take your dogs on trail walks or long walks in general if needed, I may offer house sitting services in the future.
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.
About: Hey there! I'm your friendly neighborhood dog walker! With years of experience under my belt, I'm all about giving your pup the adventure they deserve. Rain or shine, I'll make sure they have a tail-wagging good time while you're away. Let's make fetch happen! I’m currently a Stay at home parent to my 6yo and 2yo. Left the full time work scene to be more present in my family’s day to day life. I’m available during weekday and weekends. I have a fenced in yard and a silly furry boy to keep yours company. But also willing to adjust to preferences if you want your pet to stay separate! I am able to crate if needed, large crate and medium crate for medium and small dogs. Also door (“baby”) gates if crating is not preferred.
“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!”
“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!”
“Sydney was a great sitter. She was informative about Bailey while we were away. She was prompt and as well as she was able to take us last minute especially with how hectic Masters had the local area. Thank you so much and I look forward to booking her again!”
“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”
“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!”
About: I have taken care of many animals in my lifetime and I especially love dogs! My favorite thing to do in the evening after taking a walk is to cuddle with a sweet puppy, a book (or Stardew Valley) and a hot tea. In my free time I like to paint and crochet, ask me about my headscarves! I currently work part time as a secretary so I have plenty of time to spend with your pet as well as short turn around for your last minute trips. I love to take walks so I can provide any exercise needed. I have cared for shy, nervous and high energy pups. I also have experience with giving dogs medication and caring for elderly dogs. I am comfortable with multiple dog homes and I'm very flexible to your pups particular needs.
About: I’ve grown up in a veterinarian environment and i’ve just in the past two years started to work in the boarding facility.i feel in love with working with animal’s. I have one dog and 3 cats. i do pet sitting full time. i work for myself so my schedule is really flexible and easy to work with. i am available monday-sunday i am available throughout the whole day. for new clients i usually like to do a meet and greet with you and your fur babies a couple days before. i love spending one on one time with each of my babies that i take care of from going on walks and playing with their favorite toys.
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.
“Courtney did an outstanding job with Candy, who is a special needs dog. She communicated well with us and showed a genuine interest in Candy who has Cushing's Disease. Loved the pictures that she sent. I would definitely ask her back to take care of Candy!!”
About: I’ve used a different walking app before and I love being around cats and dogs! I’ve recently got a cute cat and his name is Alfred and recently Nala and they are the best thing ever! So I’m very capable of taking care of another cat and a puppy if needed and I can even take them for a walk if needed as well! I’m currently working full time M-F second shift at my job so I am available most mornings and I’m available during the weekend if needed I do live in apartment complex, but it does have a cute little play area for dogs for them to play and use the restroom if needed
“I have used Rover before in Alaska and was less than pleased with the amount of time spent with my two mini schnauzers, Nahla spend most of her time taking care of my girls during my short trip (three days). The dogs were walked everyday and they liked her a lot. It was her first time and she cooked food for them they way I do; but she did more than the Vet assistant or student I hired in Alaska and the house was still clean. Thanks Nahla”
The median cost per night for house sitting in Winfield Hill is $40
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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Book and pay through Rover’s secured platform—no cash or checks required.
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.
Meet local sitters who will treat your pets like family
1. Search
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Popular requests for house sitting - Winfield Hill
Select a filter and find qualifying sitters offering house sitting.Sitters in Winfield Hill average 4 repeat house sitting clients
FAQs for House Sitting - Winfield Hill
Frequently asked questions about Rover
As of August 2026, there are 258 sitters on Rover offering House Sitting across Winfield Hill. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winfield Hill walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winfield Hill maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winfield Hill choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winfield Hill. On Rover:
- 100% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 100% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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