House Sitting Winston
Find a loving dog sitter to watch your dog overnight in your home.
Winston, Find top rated house sitting
About: I have years of experience with every kind of dog. I am a dog sport competitor and trainer and I genuinely enjoy spending time with dogs. I have trained and worked with working and service dogs, pet dogs, puppies, and seniors! I love taking dogs out in nature and helping them have a good time. I’m currently working halftime as an office manager and have a lot of time to spend with your pet! My schedule is extremely flexible, but I am especially open during the afternoon and evening. I am able to check in on pets, spend time with them at your house, or take them out on walks. I have two Golden Retrievers that may join along if the situation allows it. Very early mornings, afternoons, and evenings are open for me.
“Adam did great with both our dogs. He sent pictures, and was responsive when we checked in on how they were doing. He was very polite and treated our home with respect while staying overnight.”
“Suzanne went above and beyond in every aspect of her stay with Lou and Lobo, walking them often, communicating clearly and sending updates. I was confident they were her primary focus and work during her stay. We would be grateful to book with her again. I rarely leave my dogs when I travel and appreciate the excellent, conscientious in home care Sarah provided Lou and Lobo.”
“I was leary about having someone stay at my house, but Krista left my house looking like no one had been there and my dogs were super happy with her. My big dog loved that she was able to bring her own dog to play with him. I loved seeing all the pictures she sent of all the dogs playing!”
About: I have had animals in my life ever since I was 4 years old. I'm pretty new to Rover, but have been petsitting by word of mouth since 2020! I've done extensive research on pets and what kind of care they prefer, what kind of diets are healthiest for them, and all the details that bridge the gap between their domestication and their primal instincts. I will provide loving care to dogs, cats, and other small animals like birds, hamsters, rabbits etc, and I will leave your house in just as good, if not better, condition than I found it! I work full time, but my schedule at work is incredibly flexible, so I am available on weekdays and weekends. I can take animals on walks if needed, or just be there to feed them and let them out daily. I am very flexible in terms of what services I offer, as it depends on what services you need! I can come and petsit at your house, and I can spend the night if you don't want your fluffy friends to get lonely. I can board for certain pets but not all, as I have a very picky cat of my own, so it is best to message me directly about what you are looking for!
About: My name is Celia and I have been a lifelong animal lover, trainer and caretaker. I am an anthrozoology (the study of human-animal interactions and relationships) at Carroll College graduate and focused on canines for my degree. I am offering dog walking, training, overnight pet and house/farm sitting, and up to 3 drop-in visits a day while you are on vacation. Drop in visits are 20-30 minutes and include feeding, fresh water, letting out to potty, petting and cuddling, playing, cleaning litter box if cat. I am looking forward to putting to practice all my knowledge that I have gained over my lifetime and school career. I have worked at a local vet clinic and have a diabetic cat myself, so am comfortable administering oral, topical, and injection medications and providing minor wound care. I am a lifelong equestrian and am available for horse and small farm sitting and drop in care as well! Regular horse feeding and mucking positions will be considered! I have lots of pet dog training experience and understand behavioral principals and canine body language. I can provide training walks where I work on leash manners. I have owner trained my own service dogs and assisted multiple others in training of their service dogs. I consider service dog training clients on a case by case basis. All animals are treated and loved like my own. For sitting services one 15 minute walk a day is included; you can purchase more walks for an additional fee. Dogs will be let out to potty every 5-8 hours during the day. Lots of cuddle sessions and play indoors and out (if there is a fenced yard) will happen!
“Leilani did excellent, the dogs and cats were well taken care of. She followed our written instructions and was great at keeping us updated on how things were going. The home was taken care of very well and we will definitely book her again in the future.”
The median cost per night for house sitting in Winston 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?
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests for house sitting - Winston
Select a filter and find qualifying sitters offering house sitting.Sitters in Winston average 4 repeat house sitting clients
FAQs for House Sitting - Winston
Frequently asked questions about Rover
As of September 2026, there are 74 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.
Rover.com is the simple, savvy way to find and book Winston house sitting. It's easy to find the perfect house sitter — many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Winston on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Winston house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.
Connect anywhere with the Rover app
