House Sitting Winston
Find a loving house sitter to watch over your pets and your home.
Over 28 pet parents in Winston have booked house sitting
Winston, 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.
“Wonderful sitter! I will definitely be re booking! My chihuahua is very nervous and she was able to calm her down and my chi warmed up very well to her. I couldn’t ask for a better experience with rover! Thanks again!”
“Breezy was just fabulous took care of my dogs like a they were hers. Was very comfortable that my dogs were in good hands.kept me in touch daily with pictures. Will definitely book breezy again. Thanks breezy for taking care of my dogs.”
“Laura has become like family to us. Shes trustworthy, reliable, and treats our precious pup like her own. We can fully relax knowing Adora is in her care. We highly recommend her!”
“did a great job looking after my two dogs, even my needy problem child 😅 house was spotless after the stay over, and communication was great. will book again when the time comes 😁”
“Pamela took great care of my two dogs while I was out of state for the long weekend. I was worried about leaving my 1 year old alone for so long, but Pamela left me with no concerns and I was able to enjoy my weekend without worrying about my dogs :) I will definitely be hiring her again for any future trips I take! I’m also fairly certain she tidied up my house as well, which absolutely exceeds my expectations!”
About: I have owned 10+ dogs and cats of varying sizes and maintenance levels. I am comfortable with all ages and can provide whatever extra care is needed. No dog gets treated like anything less than one of my own (who are my children). Over the last five years, I've watched pets off and on wherever I've lived in Oregon. Now that we have a homestead in southern Oregon, I'm excited to give your dogs and mine the best dog life imaginable every single day. No matter what, doggos are always at the center of our daily schedule. I work from home teaching online college courses (thank you, Starlink!), so I am available at all times for the pups. And when we are outside doing chores on the homestead, the dogs are right there with us! My partner, Michael, drives to Roseburg or Grants Pass multiple times a week and can meet you to provide doggie shuttle service to our remote homestead, which is two hours from town. Our dogs, Ghost and Ranger, are super dog-friendly and LOVE having new pups to play with. I am comfortable administering medications, working on training commands, and following whatever routine you think is best! Your dog(s) will be treated just like my own, with plenty of love, kisses, and exercise! Just let me know what you need, and I'll try to make it happen!
“Rebeca house sat for us while we spent a weekend at the coast. My golden retrievers were well taken care of. I received updates and quick responses from Rebeca, and highly recommend her!”
“Danielle and her daughter Cheyenne were wonderful pet sitters. We were away for five days for our son’s wedding, and thanks to them, we were able to enjoy the wedding without worrying about our dogs. We have two very sweet dogs, a 3-year-old and a 16-year-old senior dog. Since our older dog is more comfortable staying in his own familiar home, Danielle kindly agreed to care for them at our house. Because Danielle’s husband was in the hospital, Cheyenne stayed most of the time to take care of our dogs. Danielle kept us updated by sending pictures of them, which gave us great peace of mind and reassured us that they were doing well. We truly appreciate the love and care they gave our dogs. Thanks to Danielle and Cheyenne, we were able to focus on our son’s wedding and return home knowing our dogs were happy and well cared for. We would definitely reach out to them again whenever we need help in the future!”
About: I have been taking care of dogs and cats for about 7 years now. I started watching my friends dogs and now I have 3 cats and 4 dogs. I have been around pets most of my life. I have 4 dogs and 3 cats so I do take care of all of them daily. I walk my dogs 2 times a day sometimes only 1 at a time depending on the weather. I take care of my cats by letting them roam free in the house as well as cleaning the litter box everyday and feeding. I however do not offer boarding. Depending on the clients wishes I would make sure they are picked up after taken out on walks or in the yard to play.
About: I’ve had dogs in my life since I was 5. and have had my own dog since I was 16 and currently live in a household with 4 dogs. I even have pet sit for friends and family. Proper animal care is like second nature to me, it is my passionate I do have a part time job at a grooming salon and work 4-6 hours tuesday-friday typically. Working in a dog friendly environment I am able to work around potty breaks. Taking care of dogs is basically my whole life, we have 4 of them in our household. I also live with a dog trainer so I have a little bit of knowledge on that as well. Proper pet care is my top priority. I take care of clients animals just like they’re my own. making sure they’re fed and watered and have their enrichment time. If your dog gets along with others I will bring mine for a playmate
About: I’ve taken care of animals since I was 10, I love pet sitting for friends and family! I love all size animals and I love going on walks! I’m happy to go on long walks with dogs and I am very flexible and a good communicator. I am currently in school, Mondays and Wednesdays I’m free after 3 and almost anytime every other day! Once I quit my current job I’ll be available anytime on weekend! I love to play with animals to keep them exercised while also taking any on walks, I think nutrition is key so I’m happy to follow any diet for animals!
About: I am passionate about our animal friends and hope to add more pets to my daily life! I especially love pup time and am always excited to meet more friends. I’d love to help you and your family by offering quality, caring service to your pets. (: Currently I am offering sitting and drop-in visits seperately but due to health needs I am most able to provide exercise, energy expenditure and mental and physical enrichment either from your home or via outings. I do have a service dog that accompanies me most places and he loves making new friends, which can be a great option if yours also enjoy regular playdates. He is good with kids, cats and other dogs, if you have any questions feel free to ask! I am always open to making other arrangements based on your needs and prioritize finding accessible solutions and making accommodations to ensure your pets are able to recieve quality care. (: I am available in the morning through evening as well as overnight! I’d love to work around your schedule and to help make things as accessible as possible! Currently I am not offering boarding or daycare in my home. I am in a shared living space and unfortunately don’t have enough room for more furry friends at this time.
About: I absolutely love dogs ! They truly are man’s best friend till the end. I have two dogs of my own , whom I love very much ! I have experience in dog sitting as well as dog walking and I am passionate about providing good care and excited to meet new pups! I fit pet care into my day/week routine because I have two dogs of my own. One is a pit bull and another is a boarder collie so to say they need care is an understatement. They have the upmost energy. I will play with them and wear them out so they get a good nights sleep. With that being said we walk, hike, run, go to the beach, play fetch , etc. as much as we can. I treat my puppies very kindly , if not they’re quite spoiled. 😉 I care very deeply about animals and I aim to help when I can !
The median cost per night for house sitting in Winston is $44
Pet parents share their Rover experiences - Winston
Jenny was great! She was pleasant, caring, interested, willing, motivated and dedicated to do the best for Zenji and us. She even washed her bedding before we returned home! Jenny is friendly and is very willing to accommodate various needs within appropriate reasons
I cannot say enough, good things about Jenny! It goes without saying that she took amazing care of my home and my fur babies! But more importantly, she took care of me, the anxious pet owner away from her animals and house! She is so incredibly communicative and sends plenty of photos so that you know all is well at home while you are away. My only hesitancy in recommending her is that it will make her less available for me! I kid! She is wonderful and you would be lucky to have her caring for your house and beloved fur family!
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?
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 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
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for house sitting - Winston
Select a filter and find qualifying sitters offering house sitting.Sitters in Winston average 3 repeat house sitting clients
FAQs for House Sitting - Winston
Frequently asked questions about Rover
The average cost for House Sitting in Winston on Rover is $39.96 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of August 2026, there are 34 sitters on Rover offering House Sitting across Winston. 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 Winston 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 Winston 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 Winston 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
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