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

Winston, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Makayla did three visits a day for two days with both our dogs -- a high energy young beagle and a low-energy partially incontinent ancient shepherd-border collie mix. She handled it all beautifully with grace and enthusiasm -- feeding, walking, medicating, playing -- and cleaning up messes. All the visits were on time and for the scheduled duration, and all of the instructions were followed to the letter. We couldn't ask for a better sitter. Thanks Makayla!!”
About: I have had pets all my life, from growing up through adulthood. Your dog will become one of our family while away from you. You get 4 dog sitters for the price of 1 as we are a family of 4 looking to care for dogs in our home. That means 4x the cuddles for your pup! As I do not work during the days I will be caring for your dogs, walks are given on demand and/or on a schedule as provided by you! We live on almost a full acre of property, giving your dog ample space to run, play and get exercise. At night time, your dog has his/her choice of beds to snuggle up in as I allow dogs to sleep in all beds in my home. Please be aware that we do have 1 cat of our own. She has been around several dogs and always does well!
“Sophia did drop-in visits for my dog. My dog is extremely shy and hesitant around new people, but Sophia did a wonderful job at making her feel safe and secure. She was patient with her and took great care of her. She provided great updates and feedback with pictures. She even took time to check in on my roommate’s cat and showed him some attention and love! She was flexible when I needed her to come later than we originally planned due to unforeseen changes in my schedule - Sophia maintained great communication and was able to help me out! I highly recommend her to care for your pets!”


About: I have 2 small dogs of my own and a cat who I rescued off the streets! My cat was very feral and now she’s so loving. I’ve also took care of my cousins Doberman and pitbull which I love I just love animals and make time for my pets because they keep me motivated. I also go to college so when I’m not home my family helps care for them. In my home I have 2 dachshunds and let them out to potty and watch them to make sure there okay outside before letting them in to eat breakfast. Same thing goes for lunch and dinner. For my cat aka my sisters cat I also feed her when my sister isn’t home.
“Debora did an amazing job with my pups. She also suggested a meet and greet which I highly recommend. It really gives the pet parent a relief knowing your pups are in a great environment. I'll def rebook with Debora next time! My dogs completely adored her!”

About: I’ve had dogs of all breeds my whole life, and have been a pet sitter since I can remember. I have two high drive dogs that I’ve trained, and I’ve been a professional dog trainer for four years. I have lots of repeat clients, referrals and reviews, as well as have worked with/dog sat for a wide range of ages and breeds. I currently have a job that allows for me to work from home and I have a lot of morning, afternoon/evening availability as well as the weekends for dog walking or any drop in visits. When coming to your home, I can take your dog out for a walk, run, play, or just sit with them pending their energy level/age.
“Farrin was absolutely fantastic!!! She took the time to video chat with us to make us feel reassured about leaving our new puppy. She gave us regular updates and took some amazing photos. Our pup loved her and she made sure we didn’t have to worry about him while we were away.”

“This is our third time having Jessica over. She is very conscientious, responsive, prompt and responsible. She works hard to befriend our kitties even though they are not cooperative, and we appreciate that a lot! We feel very safe giving her access to our pets and our home! She is a blessing and we’re very thankful!”

About: I have had pets all my life. Right now I have a rescue dog from China and another dog I just adopted from the culpeper shelter! I have 2 cats as well. One of my cats is a tripod therefore needs extra attention. The other cat is an orange boy so you know he’s a handful. I am in between jobs so I have plenty of time watch your pup! My husband also works from home 2 days a week. NO CHILDREN in the home. I have a very large quiet yard to let your dog out to play (fenced in) . I have room to set up crates and food stations. Must be friendly towards other dogs and ok with being crated during bedtime.

About: I started my journey with dogs 4 years ago and have not looked back enjoying every moment since. I am a certified trainer who loves improving the relationship between human and dog. We have a dog yard plus 5 acres. All dogs stay in our extra bedroom, which is now considered the dog room. I personally have two dogs, a cattle dog and a husky mix. They are both very social with all other dogs. We like to have a good time here but I keep a very safe environment for the dogs, no fighting or picking on one another. NO DOG IS TURNED AWAY. If you think your dog is aggressive, I can and will evaluate them so that if possible, we will get them socializing with their own kind and having a great time. Thanks, have a good day! I train dogs for a living so I stay at my house 7 days a week besides when I work with clients and those lessons tend to run about an hour but no more than 2 hours! I have 9 years experience running my own kennel and have two dogs with a large fence so there will be no boredom here! I do prefer to kennel dogs for the night but as we get comfortable with each other they will start to earn more freedom! Pet care is my full time job and i wouldn’t have it any other way, it has been a blessing. I hope I can help make your schedule less stressful! While you’re away, let your dogs play! I have a five foot fenced in dog yard specifically for dogs. We also have another 5 acres that we will walk all client dogs on during their stay with us.-

“April is very easy to get along with and gave excellent care to our cat Miss Pepper. April sent me pictures of our feline at each visit and informed me of package deliveries. Upon my request she checked the water taps drip to ensure the water doesn’t freeze. I highly recommend her.”

About: Hi!! I am the owner of Pets and Pastures Pet Care, LLC. I’ve been pet sitting for over 10 years and have experience caring for a wide variety of animals including dogs, cats, turtles, and fish. Friends and neighbors have always trusted me to look after their pets while they're away, knowing they'll be in good hands. Currently, I live on a farm with two horses, three dogs, six cats, one pig, and chickens, so I’m very comfortable around animals of all kinds. I provide services in Castleton, Amissville, Rixeyville, Little Washington, Warrenton, and Culpeper. I am willing to travel to other towns. Your pet’s comfort and safety are my top priorities. I take the time to understand each animal’s unique needs and personality to ensure they feel safe, happy, and well-cared for in your absence. I offer flexible pet sitting services, including multiple daily drop-ins or dog walks. I’ll also provide daily photo updates so you can stay connected with your fur baby while you're away. I am negotiable with prices. Please feel free to reach out! I’d love to meet you and your fur babies!! I'm currently pet sitting full-time and working part time at RAWL, so I’m likely to be available when you need me. I occasionally manage multiple homes at once, so scheduling is usually not a problem. I carefully follow all instructions when caring for pets to ensure they are comfortable and happy while their owner is away. My goal is to give pet owners peace of mind so they can fully enjoy their vacation. I always make sure pets receive plenty of attention, are well cared for, fed on time, and given any necessary medications.
About: Unfortunately, working and moving a lot. I cannot give the best life to my dog and cat anymore. I had to leave them with my brother but I would love to give some support to pet owners who are busy due to work and life. Monday to Friday after 6 pm. Weekends and holidays all day long. I love going for walks, feed them, or I have them over the weekend. I would love to give a house and take care of pets in my apartment. I live by myself, but I work a 9-5 job.
About: 𝘼𝙗𝙤𝙪𝙩 𝙈𝙚 If you are looking for someone who is patient, loving, and experienced then look no further! I've taken care of animals since I was 13 years old, from owning dogs and reptiles to watching friend's pets. Animals will always have a soft spot in my heart. I worked at a doggie daycare and I am a Veterinary Science student, so I am well prepared to take care of your fur babies. I assure you that your pet will be in good hands and enjoy their time. Please feel free to message me! I look forward to caring for your pet and meeting potential new clients. 𝙒𝙝𝙖𝙩 𝙩𝙤 𝙚𝙭𝙥𝙚𝙘𝙩 Your pet will have unlimited potty breaks and water supply. I will follow their daily schedule, so when they return home to you, you are not having to readjust them. They will have comfy place to rest and be in a clean environment. I am able to take them to dog park/walking and provide mental stimulation for high energy dogs. Thank you for reading this far and please message me if you have any questions😁 Sincerely, 4 Legged Animal Lover I am very attentive to their needs and I am home full-time. I can provide consistent communication to ease any worries you may have s I will care for your pet as if they were mine and you will recieve videos/pictures to keep track of their stay with me. They will have comfy bedding and friends (my pets) to play with 🐾.**Please let me know if your pet doesn't get along with cats/dogs I will keep them separate. I vaccuum up all the hair, clean, and disinfect from previous clients. Your pet's bowls will be cleaned daily to prevent germs. I only accept pets that are vaccinated and I take one client at a time. I also really love animals, so they are going to have the best care with me!😄
About: With aspirations of becoming a Veterinarian I have combined 6 years experience in the Veterinary field, and 7 years working with animals. I own 6 dogs all of varies breeds, along with the occasional foster pup or two. While in my care your fur baby will have ample amount of structure play, to ensure 100% safety I keep play groups small with some one on one time play. I have a wide variety of experience with reactive dogs as well, if your dog does not do well with others open communication is all I ask and I will ensure your loved one is fulfilled during their stay. I work from home allowing my schedule to be pretty flexible, I am happy to offer pick up and drop off services if needed or work around your schedule I have a fully fenced in yard with access to trails and parks, where I enjoy spending as much time outdoors allowing all the pets in home to feel enriched
About: ✅ 𝙁𝙞𝙣𝙙 𝙢𝙤𝙧𝙚 𝙙𝙚𝙩𝙖𝙞𝙡𝙨 𝙤𝙣 𝙤𝙪𝙧 𝙔𝙤𝙪𝙏𝙪𝙗𝙚, 𝙏𝙞𝙠𝙏𝙤𝙠, 𝙖𝙣𝙙 𝙁𝙖𝙘𝙚𝙗𝙤𝙤𝙠 𝙥𝙖𝙜𝙚𝙨 𝙗𝙮 𝙨𝙚𝙖𝙧𝙘𝙝𝙞𝙣𝙜 𝙛𝙤𝙧 𝙏𝙧𝙖𝙞𝙡𝙗𝙡𝙖𝙯𝙞𝙣𝙜 𝙆9 𝘼𝙙𝙫𝙚𝙣𝙩𝙪𝙧𝙚𝙨. Hey there, Pet Parents! Nice to meet you virtually! I'm Seyla, a dog enthusiast who's finally living the dream of having a furry companion. You see, my childhood dream of owning a dog was delayed due to public housing restrictions, but now that I'm a proud homeowner with a fenced yard, I've got my paws full! Currently, I share my home with four fantastic dogs who are not only friendly but also well-trained. My very first four-legged friend was Bruno, the Rottweiler, and we've been inseparable since he was a pup. Bruno received top-notch training at Apple Jack's K9 in St. Mary's County, and I've been using the valuable tools and techniques I learned there ever since. As if four dogs weren't enough, I'm also a part-time volunteer at "Rescue Angels of Southern Maryland," where we rescue animals from less-than-ideal situations. And, on top of that, I've opened my heart and home to foster dogs from the Humane Society of Charles County. It's safe to say that I have a deep and abiding love for our furry friends! So, why should you entrust your fur baby to me? Well, I've got about 8 years of hands-on experience caring for dogs, and I genuinely believe I offer the best boarding and doggy daycare service around, spanning a radius of at least 50 miles (if not more). Don't just take my word for it—visit our Facebook page (spRover80) to watch videos, view pictures, and read the glowing reviews. You'll see for yourself that you're getting the most bang for your buck! If you adore your dog as much as I love mine, I understand how nerve-wracking it can be to leave them with someone new. But I'm here to show you just how much I adore dogs by offering an array of wonderful activities. Your furry companion will join me on invigorating hikes and walks (twice daily), covering 1-2 miles each time, as we explore some of the finest parks (see below for the full list) in Southern Maryland, at least in my opinion! For those who enjoy a leisurely ride, your dog can hop into our doggy bike trailer as we embark on 2-7 mile adventures. And when the weather warms up, we've got a swimming pool for our canine guests to cool off in. Inside the house, your dog will have the run of the place (provided they're house trained), and they can choose from an array of toys to play with. To keep them well-hydrated, we have water stations throughout the house stocked with purified water, regularly cleaned and refilled. Rest assured, your furry friend will be in great hands, and we'll make sure they have a tail-wagging good time during their stay! Parks & Trails: 1. Smallwood State Park 2. Friendship Farm Park 3. Pisgah Park 4. Purse State Park 5. Doncaster Demonstration Forest 6. Douglas Point 7. Mallows Bay Park 8. Chapman State Park 9. Chapel Point State Park 10. Indian Head Trail 11. Myrtle Grove WMA 12. Port Tobacco River Park 13. Tayloe’s Neck Forest 14. Piscataway Park 15. Turkey Hill Park 16. Thorne Gut Tract 17. Thomas Stone Historic Site My better half and I are both 'work-from-homers,' so you can bet your dog's last chew toy that there'll always be a pair of eyes on them. We won't even let them sneak off to the bathroom alone! Here in the wilds of Indian Head, Maryland, we've got a sprawling 1-acre playground enclosed by a fence that's taller than Shaq (okay, maybe not that tall, but it's secure). I've gone all James Bond with 21 motion detectors and security cameras, ensuring that every nook and cranny is under surveillance—inside and outside! We're serious about safety, folks! Now, here's the deal: we're all about accommodating friendly dogs. Your pet's safety is our mission, like it's our secret spy mission! 🕵️♂️🐾 And for those sneaky escape artists, the ones who think they're auditioning for the next great canine escape movie, we've got a secret weapon – the Fi GPS collar. If your dog has a history of vanishing acts or tends to pull a Houdini, consider it their high-tech tracking device for the duration of their stay. Thanks a million for taking the time to read my profile, and if you've got any questions, don't hesitate to shoot me a message. We're here to make sure your dog's adventure with us is safe, secure, and seriously fun!
About: Taken care of animals for over 10 years, held snakes, rode horses, pet tarantulas, I've been able to identify when dogs need to be left alone and when they were in danger or Ill could identify my dog had kidney stones, deeply care for animals and can walk, play, and be their best friend lol No job currently unemployed and I love animals so I'm chilling at the home right now for this year until I get married period and then I'll stay home even longer! I am able to really do anything you ask of me all I ask is that you let me care for your pets more than once! I will offer really lots of bonuses because I care
The median cost per visit for pet sitting in Winston is $20
Pet parents share their Rover experiences - Winston
Makayla did three visits a day for two days with both our dogs -- a high energy young beagle and a low-energy partially incontinent ancient shepherd-border collie mix. She handled it all beautifully with grace and enthusiasm -- feeding, walking, medicating, playing -- and cleaning up messes. All the visits were on time and for the scheduled duration, and all of the instructions were followed to the letter. We couldn't ask for a better sitter. Thanks Makayla!!

Katie is PHENOMENAL! My dog has epilepsy and requires medication every 12 hours exactly! This makes traveling very difficult as her morning pills are at 6 am. Katie was punctual every single day where I usually worry endlessly about my dogs, this time I found myself forgetting to check in on how they were. When my travel got extended a week, Katie was available to help with their morning feedings and medication. She is AMAZING and I’m excited to be booking her for all of my upcoming trips!

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 to book pet sitting

1. Search
Browse profiles of sitters near you who offer pet 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 pet sitting - Winston
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winston average 5 repeat pet sitting clients
FAQs for Pet Sitting - Winston
Frequently asked questions about Rover
As of November 2026, there are 975 sitters on Rover offering Pet Sitting across Winston. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
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.
Yes, you can find sitters who have experience with handling special pet needs in Winston. On Rover:
- 89% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 97% 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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.




