House Sitting Winston
Find a loving house sitter to watch over your pets and your home.
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.
“Deborah stayed at our home to take care of our two doggies and our kitty while we were gone for the weekend. She was wonderful! Very attentive, providing updates and giving them lots of attention. Our one dog is on meds and the others are on special diets. Highly recommend Deborah for taking care of your fur babies and looking after your home.”
“We had an amazing experience with Melissa! She stayed in our home for a week with our two dogs, one of whom has severe anxiety. She took the time to do a meet-and-greet beforehand, gave him the space he needed, carefully read his body language, and earned his trust. She was reliable with his daily medications and patient in helping him feel comfortable. Our home was left spotless and respected, and it was clear she treated both our dogs and our space with great care. She even surprised us with a kind and thoughtful gesture at the end of the stay, which meant so much to our family. We are so grateful to have found her and would 100% book with her again. Highly recommend to anyone looking for a caring, dependable, and professional sitter!”
“Madyson is the most responsive sitter I think I have ever had. She responds promptly to any messages I send her and sends me regular updates which is important to me so I don’t worry while I’m away. She doesn’t do anything we haven’t discussed without checking with me first and always lets me know her schedule. We came home to happy dogs and cats and a house cleaner than when we left. I am so happy we found Madyson!”
“We had an amazing experience with Farrin as our pet sitter for our dog, Taco. She took excellent care of him overnight, making sure to give him plenty of playtime and cuddles while we were away. Farrin was respectful of our home, leaving everything clean and tidy, which we really appreciated. She even came by for a meet and greet before the booking, giving us peace of mind. We would absolutely book with Farrin again in a heartbeat! Highly recommend her!”
“Erica was fantastic with our two miniature wires hair dachshunds. She stayed at the home and kept our dogs company while we were away over the Thanksgiving week. She kept us updated through the week and took them for walks. We highly recommend her.”
“Anastasia took great care of our somewhat difficult Shiba Inu, Stitch. She was patient in getting Stitch to warm up to her and was willing to send us pictures throughout the week. Would definitely recommend her to watch your fur baby!”
“Elizabeth was the perfect house sitter and companion for our dog, Pringles! Her communication and service were superb. We will definitely invite her back!”
“Ronda was not only efficient and responsive, sharing twice-daily feedback about the care and feeding of our two kitties, but she was also able to establish an affectionate bond with them during our 16-day absence. We are pleased to give Ronda 5 stars and would highly recommend her.”
“Olga and Stepan took great care of both Loki my families cat and Rithie my dog. Asked very good questions on their care and comforted my dog when there was a thunderstorm :) I will absolutely be booking them agian”
“Cindy went out of her way to make sure my dog felt comfortable with her before we had her stay at the house. She was very responsive to communication and sent pictures which I appreciated greatly.”
“Such a nice young Lady. Shes like a dog whisperer, they loved her instantly! My dogs dont get that excited when I come home! Top notch! I would give her ten stars if I could. Madison went above and beyond!”
“Scott and Sarah were fantastic. I really appreciated their level of communication, care, state in which they left my home. They pay attention to the details. Every picture I received of my dogs, it looked like they were smiling ear to ear and have the best days. So cute.”
“Billy was the perfect Dog Sitter. All four of my dogs loved him immediately. He took such good care of them. He was prompt, courteous, attentive to all of my dogs. He was fantastic, and I will certainly use him again.”
The median cost per night for house sitting in Winston is $50
Pet parents share their Rover experiences - Winston
Katie is lovely- she is responsive, communicative, responsible and was so loving to our pets. Our large dogs are not easy to handle at times, and Katie dealt with them beautifully. We appreciate her so much and will use her services over and over again! Our boys miss her already! 🐾💙
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 3 repeat house sitting clients
FAQs for House Sitting - Winston
Frequently asked questions about Rover
As of August 2026, there are 556 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 with handling special pet needs in Winston. On Rover:
- 95% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 95% 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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