House Sitting Winston
Find a loving house sitter to watch over your pets and your home.
Over 38 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.
“I absolutely adored Penny, she took great care of my animals but also knew I had a stressful day returning to my kiddos that she got the house ready for me and honestly it was amazing. I will forever only hire her for anytime I leave for another holiday.”
About: I’m all about fun, friendly energy on every walk. Your pup gets to explore, play, and enjoy a safe, joyful journey every time we hit the pavement or grass! I have tons of pet care experience: I have two senior dogs of my own, aged 13 & 15, who I’ve had since they were old enough to be without their mommas; I’ve worked as a pet specialist at a boarding facility for dogs and cats; and I pet every dog I meet—with permission, of course. Like everyone, I love dogs, and would love to give yours some company on a play visit or walk! I work from home, and have a flexible schedule. I prefer to have a two-day notice, so I can make sure I’m available when you need me, but depending on the day, I could be available same-day too. Just contact me and see! I do not care for anyone’s pets but my own in my home. But in a client’s home, I care for pets by giving them what they need—I think it really depends on the desire of the client and the pets! Case by case basis. Belly and chin scratches are always a given though!
“Cathy is great with the pups and this for this visit was a life saver for us. My husband was able to have her trouble shooting the power outlets in the garage to get the garage door opener working again and restore power to the refrigerator and freezer! Go greatly appreciated!!”
About: I am a 47 year old male, whose Air Force duties were crew chief for F-22 fighter jets, serving overseas during the Iraq war. I have top secret security clearance and many missions under my belt. My passion now is animals. I am currently an SPCA foster parent to both dogs and cats. No job is too big or too small when caring for your pet. Whether they have medical needs or just need a happy face to lick, I can take care of it all. I am available day or night with total peace of mind everything will be cared for. I live in South Lakeland. I am retired and available for boarding, client home boarding and care, pet walks and visits. I'm available any day and time. I will answer all requests as soon as I see them. I live alone in a small and safe community, with little traffic, which makes it safe for walks. I have a unfenced yard but I take great care allowing the dog to have freedom in the yard while being on a leash. I have access to a fenced in dog "play" area in my community. My home is non-smoking, cozy, and quiet. I keep the home air cool to provide comfort for the animals. I maintain constant contact with your loved one to know they are safe and happy. I will provide daily texts and photos of the pet, to the owner, to show they are safe and happy.
“Elizabeth was great to work with. She was on time, followed instructions perfectly and most importantly my pups had a great time with her and were well cared for. Thank you!🙏 we will be happy to have you back.”
About: I’ve been raised with a variety of pets since I was a kid. I’ve been pet sitting since college. I have experienced with younger dogs as well as senior dogs. I have a flexible summer schedule for pets that need more care. During the school year, I have a later start and am able to let pets out during lunch. I have experience working with crate trained dogs as well as high energy dogs. I have also worked with pets with special diets or medication needs.
About: I’m patient with all animals and love their energy they bring to my life. I’ve cared for animals since I was 2 years old and I’ve been connected with them ever since. I currently work a full time job that does allow me to have free time after work or weekends to care for cats and/or dogs in my free time. Although I don’t have a fenced area at my apartment complex I do have plenty of space to walk and we can always go to a park enjoying the scenery.
“Lyndsay was super communicative with me from start to finish. My flight got delayed and offered to stay a few extra hours past what we agreed upon. She sent me pics of my babies throughout the day and the entire weekend. I highly recommend her and trust her with my pups!”
“Christina was amazing with our senior dogs. One has epilepsy and the other one other health issues, so they are not that simple to take care of. She did a great job taking care of them. They were very happy with her and not stressed out. She kept me informed the entire time, was responsive, sent photos, and was able to give them their meds and vitamins. She stayed over and was respectful of our home. We recommend her and will be hiring her in the future.”
About: My family has always had pets. Dogs, fish, and ferrets. Love these furry creatures like no other and would love to share my love to your pet. I am working part time in the field of Applied Behavior Analysis. I work with children with Autism by the day and can care for animals in the afternoon and evening. I am great at walks, play time, feeding, and cleaning up after pets. I own a boxer and care for him appropriately while also providing love and attention.
About: I have had a dog since I was 5, she is currently 15. I care for her greatly and will do anything to keep her happy and healthy. I would do the same for anyone else's pet while their owner is away. I am available while I am home from college all the time. I am willing to take care of an animal to the best of my abilities any time of the day. I follow the instructions given by the owner very well so the change does not harm the animal. I have a fenced in backyard and one medium sized female dog. If boarding at my home, the dog(s) would need to be good with female dogs. I will ensure the dog is very well taken care of while in my care.
“Christian was amazing with our 4 dogs!!! He kept us up to date every day on how they where an that eased my mind so much!!! They dogs love playing outside with him so much an that made for good nap times an better bed time!!!”
“Miranda was a godsend! I couldn’t have asked for a better pet sitter for my puppy. From the beginning, she was reliable, communicative, and clearly cared deeply about making sure my puppy felt safe, loved, and comfortable while I was away. I received regular updates and photos, which gave me so much peace of mind. When I came home, my puppy was happy, well cared for, and clearly attached to Miranda — which says everything. Miranda paid attention to routines, gave lots of playtime and affection, and treated Lola like family. It’s such a relief knowing I have someone I can completely trust with my fur baby. Highly recommend to anyone looking for a caring, dependable, and attentive pet sitter!”
“We are so thankful for Mattison! She was wonderful with our Frenchie and our kitty. Very caring and so loving! She kept us updated with messages, pictures and videos which we loved. She is highly recommended and we can’t wait to book her again ! Thank you again Mattison!”
“My baby Eden is a handful. She is an eleven year old treewalker coonhound rescue who was never fortunate enough to live in a house. There are a lot of instructions when I have somebody watch her. Abigail did a great job! I also have a cat and two guinea pigs and she took wonderful care of them also. She kept me updated and sent pictures while my kids and I were in Florida for 7 days. I would definitely have her watch my fur babies again. If she is up for it lol.”
“Found Rosemary to be very reliable in taking care of our pets. She was attentive to our instructions and flexible to unexpected changes. She kept us informed and updated. We really appreciate not having to stress knowing the pets were being taken very good care of while we were away.”
The median cost per night for house sitting in Winston is $47
Pet parents share their Rover experiences - Winston
Penny did a great job. She house sat for our dog and cat and did a wonderful job. She sent us photos and kept us updated on how they were all doing. She was very respectful of our home and our pets, and we have already booked her for another much longer visit in a month.
Megan was wonderful! We had a great first meeting, communication was great she was fast at responding and friendly. She sent us pictures of our pets while she was watching them and they were all happy when we got back home. I would definitely recommend her to anyone and I’d use her again.
Sia sat for our young dog at our home for a long vacation and she was wonderful! Teddy loved her, she provided regular updates and photos . She worked with him on playing fetch and taught him “Stop” while on walks. It was comforting to know our dog and our home were well cared for while we were gone. We will definitely use her again and highly recommend anyone else to use Sia if she is available.
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winston sitters!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 $44.4 per night (as of July 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 July 2026, there are 2,654 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:
- 88% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 98% 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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