Pet Sitting in Winston
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winston pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Keshia was amazing! She left wonderfully detailed notes and it was great to feel like the person taking care of our girl actually cared! I highly recommend Lakeshia and will definitely be using her services in the future!”



“Rover review: Parker (Hannah) is an outstanding Rover representative! Our pet babies (2 doggies & 2 kitties) love Parker and welcomed her with love every time she came to care for them 3x a day. We appreciated the fantastic pet pics Parker sent us, and the love that Parker gave to our babies while their parents were away is invaluable.”


About: I have ample room and time to love on your fur babies!! I currently do not have any dogs but love them all! I also have a basement with a separate gate if your pet needs space by itself. I live close to the mountains so if you want to take the day to hike/explore sperryville I am your go to:) I work from home and love my animals!! I am fortunate to have the flexibility to take care of my farm animals and others when needed. I own a small farm with plenty of space for walking and also have a fenced in garden than I can use during the colder months for secure play for dogs.


“Look no further — and eliminate all worries and concerns about leaving your pet — when seeking the services of a kind, gentle, conscientious, thoughtful, generous and big-time lover of dogs! Rhonda in Culpeper is your first … and only choice! She took such loving care of our Gracie that after our return home she kept wandering around the house, looking for her new friend, Rhonda! Rhonda even took special care to tuck in our parakeets at night. When we found out — late — that a delivery of perishable food was arriving, Rhonda even took the box in, opened it and placed the food items on our freezer. Our care of Gracie was special! Daily reports! Daily photos! Texts! Rhonda is fate-out amazing! She will be our only go-to when looking for someone to care for Gracie. She is special!”


“Ashley is the best person you can have caring for your babies. She went above and beyond for an entire week for my various pets, which included poultry- even in bad weather! I am so grateful to her and highly recommend her for any pets you have.”


“Noel is amazing! So kind and loving to my very new to me puppy and took excellent care of her. As my first Rover experience, I was very nervous. Noeli is professional and would highly recommend her again.”



“Absolutely terrific! She was reliable, communicative, and caring. Our dogs, even our asshole chihuahua, took to her immediately! We will definitely use Kimberly again. Thanks for taking such good care of our boys, Kimberly ?”


About: I've taken care of sick dogs, dogs on diets, and dogs that are used to a routine, but am able to take care of any situation. I love to be around animals and will happily make sure your dogs are kept safe and happy. I work Full-time Mon, Tues, Thurs, and Friday from 8:30 - 4:30 and Wed from 11 -7. I am happy to come "home" each day after work to your home and stay during the workweek, I just will not be able to be with them until after work during the week. I am fully available on most weekends, so just let me know what works! For the dogs I have taken care of before, I always walk with leashes, even for well trained dogs, I will be new to them. I always pick up after dogs on walks. I have owned cats and dogs all my life, and am very comfortable with any dog or cat. I will keep doors locked when inside and of course when leaving the house.

About: If you have any questions about my services please reach out to me. I am willing to be as flexible as I can. Since I am in school through Monday - Friday. But I am available all day and all night on the weekends. I have my own pet. He is a rag-doll cat and he requires a lot of attention throughout the day which I love because he is very interactive. I love to cuddle with my pet and any other animals that I can get the opportunity to cuddle and pet. I love playing, walking and just simply hanging out with any pets.

About: I love animals. I will take the best care of your pet. I'm fine with handling aggressive ones and bigger dogs too. I've taken care of animals all my life, so you can travel without a worry. Right now I'm open any day and time. I can overnight stay and house sit as well. I'm a fan of cats and other animals too. I'll follow your instructions to the letter. I will always call for questions and not assume something on your property. I'm fine with taking videos and pictures

About: Animals—especially dogs—are my passion! I have over a decade of experience pet-sitting and grooming dogs, and have owned, fostered and cared for dogs, cats and exotic pets of all breeds and sizes in my home since I was very young. I have always been particularly passionate about caring for and working with dogs. I am the proud owner of two Australian Shepherds, who I enjoy training in behavior and agility. If you're in need of someone who is loving, patient and trustworthy to look after your dog(s), please don't hesitate to reach out! I look forward to having the opportunity to care for your beloved fur babies, and promise to love them like they’re my own while you’re away. *I have experience working as a dog groomer—I offer bathing services at an additional cost! Feel free to ask.* I currently work remotely full time, so I am available 24 hours a day, 7 days a week to provide attentive care to your dog(s). I have a fenced-in backyard and two friendly Australian Shepherds to keep your dog company. Your dog will have as much supervised outside play time as they would like, and will have free roam of the main floor of my house at other times. If you prefer your pet to be crated at times, just let me know your preference and I’ll be happy to accommodate. ***Note: to avoid stomach upset/any allergic reactions, dogs in my care will ONLY be given food and/or treats supplied and approved by their owner. Additionally, to help protect my family, home and other dogs in my care, I ask that owners please ensure their dogs are up to date with flea/tick/worm preventative. If parasites are found, a $100 cleaning fee will apply.***

“Mikayla is great! Highly recommend her to take care of your fur babies. She is super attentive and will love your babies as her own. She took care of my 3, 2 German Shepherds & a cocker spaniel, she did an excellent job, took them on walks 3 times a day right on time and made sure they were well feed and had clean water. Played and spend time with them at each visit, that when we got back we knew that they were well taken care of and happy! Mikayla fills out the Rover card each time and includes a lot of pictures-which I love because I get to see how much fun they we having and be part of their day. Thank you Mikayla for everything! We appreciate all your help and look forward to booking again in the future!”


“Courtney was awesome! She came to visit prior to her drop in so I could introduce her to Walter and go over some things. During her drop in she sent me a bunch of pictures and gave me a whole run down as to what they did. It was truly a blessed feeling that he was being taken care of well!!!”

About: Hi, my name is Michelle! I’m currently in high school looking for a job for after school and on the weekends. I absolutely love animals, and would love to help our furry friends in our community. I have experience with cats, dogs, and chinchillas! I've been taking care of dogs since I was about 9 years old, I love animals I have a cat, 3 chinchilla’s and a dog, they’re all friendly and get along with other pets. I’m currently going to school Monday, Wednesday, and Friday from 8:00 am till 3:15. I also look after all my pets and stay at home after school. In my home I let pets on the couch and beds. I love watching them be comfortable and happy. I’ll follow every rule my client give’s me in their home and in mine.
Loving pet sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Stephanie H.Star Sitter

“Stephanie always loves on our dogs and spends quality time with them. I feel so comfortable with her taking care of them when we will be gone all day.”


Lakeshia W.Star Sitter

“Keshia was amazing! She left wonderfully detailed notes and it was great to feel like the person taking care of our girl actually cared! I highly recommend Lakeshia and will definitely be using her services in the future!”




Hannah B.
Star Sitter


“Rover review: Parker (Hannah) is an outstanding Rover representative! Our pet babies (2 doggies & 2 kitties) love Parker and welcomed her with love every time she came to care for them 3x a day. We appreciated the fantastic pet pics Parker sent us, and the love that Parker gave to our babies while their parents were away is invaluable.”


Whitney G.
About: I have ample room and time to love on your fur babies!! I currently do not have any dogs but love them all! I also have a basement with a separate gate if your pet needs space by itself. I live close to the mountains so if you want to take the day to hike/explore sperryville I am your go to:) I work from home and love my animals!! I am fortunate to have the flexibility to take care of my farm animals and others when needed. I own a small farm with plenty of space for walking and also have a fenced in garden than I can use during the colder months for secure play for dogs.




Ronda S.
Star Sitter


“Look no further — and eliminate all worries and concerns about leaving your pet — when seeking the services of a kind, gentle, conscientious, thoughtful, generous and big-time lover of dogs! Rhonda in Culpeper is your first … and only choice! She took such loving care of our Gracie that after our return home she kept wandering around the house, looking for her new friend, Rhonda! Rhonda even took special care to tuck in our parakeets at night. When we found out — late — that a delivery of perishable food was arriving, Rhonda even took the box in, opened it and placed the food items on our freezer. Our care of Gracie was special! Daily reports! Daily photos! Texts! Rhonda is fate-out amazing! She will be our only go-to when looking for someone to care for Gracie. She is special!”


Ashley F.

“Ashley is the best person you can have caring for your babies. She went above and beyond for an entire week for my various pets, which included poultry- even in bad weather! I am so grateful to her and highly recommend her for any pets you have.”


Noeli F.

“Noel is amazing! So kind and loving to my very new to me puppy and took excellent care of her. As my first Rover experience, I was very nervous. Noeli is professional and would highly recommend her again.”




Kimberly J.


“Absolutely terrific! She was reliable, communicative, and caring. Our dogs, even our asshole chihuahua, took to her immediately! We will definitely use Kimberly again. Thanks for taking such good care of our boys, Kimberly ?”


Alexander H.
“Alex is top notch! Our pups love spending time with him and are always excited to see him arrive. He has spent overnights caring for their every need(they are needy) and I highly recommend Alex to care for your pets”


Makayla M.

“We will use here again. She was great”


Madison T.
About: If you have any questions about my services please reach out to me. I am willing to be as flexible as I can. Since I am in school through Monday - Friday. But I am available all day and all night on the weekends. I have my own pet. He is a rag-doll cat and he requires a lot of attention throughout the day which I love because he is very interactive. I love to cuddle with my pet and any other animals that I can get the opportunity to cuddle and pet. I love playing, walking and just simply hanging out with any pets.


Billy C.
“Billy was very professional at the tasks I asked for and had constant updates like I requested while he was house sitting and watching my pets. Honest and hard working”


Jessica W.Star Sitter
“I have never experienced a person more caring and kind with our pets. Jessica goes above and beyond every time! Its like our dog comes home happier and better off then when we left her. Jessica’s children are Soooo good with animals too. Its like the best place we never dreamed we would find. We plan our trips around her availability when possible! No kidding!!! Thank you Jessica and family for being the safest place for our little girl to stay and thrive❣️💖”


Mikayla S.

“Mikayla is great! Highly recommend her to take care of your fur babies. She is super attentive and will love your babies as her own. She took care of my 3, 2 German Shepherds & a cocker spaniel, she did an excellent job, took them on walks 3 times a day right on time and made sure they were well feed and had clean water. Played and spend time with them at each visit, that when we got back we knew that they were well taken care of and happy! Mikayla fills out the Rover card each time and includes a lot of pictures-which I love because I get to see how much fun they we having and be part of their day. Thank you Mikayla for everything! We appreciate all your help and look forward to booking again in the future!”


Courtney R.
“Courtney was awesome! She came to visit prior to her drop in so I could introduce her to Walter and go over some things. During her drop in she sent me a bunch of pictures and gave me a whole run down as to what they did. It was truly a blessed feeling that he was being taken care of well!!!”


Michelle A.
“Michelle is the sweetest animal lover I know!! She shows so much love and care for our furry friends. She’s very attentive and reliable! Highly recommend!”


Stephanie S.

“Excellent care! Stephanie even sent photos of Mia so we could see how she was doing.”


Tiffany D.

“Tiffany took good care of my girls.”


Emily B.

“Emily was super nice and was great with my kitten Jojo she followed every instruction we left and she took the cutes pictures of my fur baby!”


Kelsey P.

“Excellent care and effort. Kelsey was kind and understood mine and my cat’s needs while I was away. Very communicative as well. Will definitely use her again.”
Popular requests near you
Select a filter and find qualifying Winston sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for pet sitting in Winston is $20
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 pet 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.
Sitters in Winston average 7 repeat pet sitting clients
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winston on Rover as of Aug 2025 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 69 pet sitters in Winston. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 93% of Winston pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winston.
Rover makes it easy to find Winston pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 69 pet sitters in Winston on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
