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.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

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.

1 / 1
Sitter Profile Image: Tiffany D.
Verified Enhanced Background Check
Tiffany D.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
207 reviews
77 repeat clients
20 years of experience
Richmond, KY, 40475

Tiffany was great, despite the 7 lbs of screaming tiny dog. That she was willing to try with Duke was awesome, and I appreciate it so much! Of course our old man, Pimp'ns, loved her, and he's the one that matters (old, can't hold his bladder all day any more). Thank you!!

Profile image
Heather R.
Sitter Profile Image: Alicia R.
Verified Enhanced Background Check
Alicia R.
from
$17
per visit
5.0 out of 5 stars
56 reviews
12 repeat clients
12 years of experience
Irvine, KY, 40336

Alicia has been our sitter for a few weeks now, coming to the house twice a week while I’m at school—and she’s done a wonderful job! She’s reliable, quick to respond, kind, and clearly loves what she does. I always come home to a happy, relaxed Lassie. Alicia goes above and beyond to make sure Lassie gets plenty of fetch time and potty breaks. I highly recommend her!!

Profile image
Selena M.
Sitter Profile Image: Terry A.
Verified Enhanced Background Check
Terry A.
from
$14
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
25 years of experience
Irvine, KY, 40336

Very knowledgeable and thorough. My cat was very unimpressed when we got home, simply because she was very relaxed and at peace being taken care of by T.J.

Profile image
Michelle G.
Sitter Profile Image: Heather R.
Verified Background Check
Heather R.
from
$25
per visit
5.0 out of 5 stars
16 reviews
3 repeat clients
40 years of experience
Richmond, KY, 40475

When I was planning a trip out of town and my original sitter fell through, Heather was able to make availability short notice. She took excellent care of my kitty, giving me updates and pictures every day. She definitely went above and beyond and I felt so much better about being away knowing that she was taking care of my old man cat.

Profile image
Ashley M.
Sitter Profile Image: Tyler S.
Verified Enhanced Background Check
Tyler S.
from
$15
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
5 years of experience
Richmond, KY, 40475

Tyler was on time and courteous. Both Boone and Ava loved him and he sent lots of photos and video updates. We would love to have Tyler back in the future!

Profile image
Rachael & Jacob C.
Sitter Profile Image: Lexi L.
Verified Enhanced Background Check
Lexi L.
from
$13
per visit
5.0 out of 5 stars
2 reviews
8 years of experience
Richmond, KY, 40475

About: I’ve had dogs since I was a kid. I’ve cared for friends and families dogs of all sizes and ages. I currently have a female American bully but in the past I’ve had English mastiffs, pit bulls, and a border collie. I enjoy high energy dogs that love to run and play as well as older dogs that just want to play around and be loved on. I’m currently on summer break. I am an athlete at Eastern Kentucky University and have required practices every day but I’m gone no longer than 3 hours per day. I currently live in an apartment with a dog park on site I also have one friendly and very active pup to keep yours company. I will always be outside with the pups they are never out there alone.

Sitter Profile Image: Christopher C.
Verified Enhanced Background Check
Christopher C.
from
$15
per visit
10 years of experience
Berea, KY, 40403

About: I've taken care of friends and families pets for the past 10 years, I've worked in pet retail for more then 9 years. My growth and passion for animals is every evolving I currently work a full time job, so I have 2 rotating days off a week plus off every night. Schedule and times can always be discussed. I have 8+ years of pet education along with nutrition and training, I have more then 40 hour of positive/ positive reinforcement training to help keep things under control.

Sitter Profile Image: Elena S.
Verified Enhanced Background Check
Elena S.
from
$40
per visit
5.0 out of 5 stars
33 reviews
12 repeat clients
5 years of experience
Richmond, KY, 40475

Elena is AMAZING!!! She is so sweet, kind, caring, patient and very accommodating. Our dog, Sydney is very shy and nervous around people, but she quickly warmed up to her. Elena took great care of Sydney. She gave detailed feedback, updates and pictures of Sydney during each visit. I will definitely rebook with Elena again. I highly recommend and trust her! Elena is the BEST!!!

Profile image
Charlene B.
Sitter Profile Image: Cindy H.
Verified Background Check
Cindy H.
from
$15
per visit
4.7 out of 5 stars
13 reviews
6 repeat clients
25 years of experience
Richmond, KY, 40475

As always, Cindy was excellent with Willow. It was storming so she sent a message and asked how Willow does with storms. It was so nice that she checked. But that’s how seriously she takes her appointments.

Profile image
Patti W.
Sitter Profile Image: Molly D.
Verified Enhanced Background Check
Molly D.
from
$13
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
20 years of experience
Richmond, KY, 40475

About: I’ve been surrounded by animals my entire life—I’ve never known a home without a dog. Growing up, I had the opportunity to care for dogs of all sizes and temperaments, from energetic Jack Russell Terriers to loyal Labrador Retrievers and loving Pitbulls. I was always involved in their daily care, whether it was taking them on walks, feeding them, or making sure they stayed up to date with vet visits. My love for animals has only grown over the years. Two years ago, I adopted my dog, Russell, from a shelter, and he has been my loyal companion ever since. I also have two cats, Chief and Reid, who keep life interesting and have taught me even more about pet care. Caring for animals isn’t just something I do—it’s something I’m truly passionate about. I love making sure pets feel safe, happy, and well cared for, and I treat every animal as if they were my own. As a part-time Graduate Assistant, I have plenty of flexibility throughout the day to care for and play with your pups, especially on the weekends! As a dog owner myself, I know what it's like to worry about your pet while gone. I will ensure pets are fed, exercised, and groomed according to their needs. I provide loving companionship, and follow specific care instructions for each pet’s well being and comfort.

Sitter Profile Image: Kailey B.
Verified Background Check
Kailey B.
from
$20
per visit
5.0 out of 5 stars
23 reviews
4 repeat clients
12 years of experience
Richmond, KY, 40475

Kailey has been absolutely wonderful with my dog, Sable. She’s dependable, punctual, and communicates clearly, which gives me real peace of mind while I’m at work. Sable took to her quickly, and it’s obvious Kailey genuinely cares about the dogs she works with. She’s flexible with my rotating schedule and always professional. I truly appreciate her reliability and would highly recommend her to anyone looking for a trustworthy and caring dog walker.

Profile image
Louis D.
Sitter Profile Image: Alexis T.
Verified Enhanced Background Check
Alexis T.
from
$20
per visit
15 years of experience
Richmond, KY, 40475

About: I grew up in a house with dog lovers, so we had as many as 4 dogs at one point! We have had dogs from puppies to final days! I'm super comfortable with any breed! I'm currently a PA student, so my availability is pretty flexible. I'm usually always free on the weekends when most people need pet sitters for exciting weekend plans! I'm usually always free in the evenings during the week, as well. I can do whatever you need for your fur baby while away! I know how it is to be so nervous that your babies aren't taken care of while you have relatively no control since you aren't home! I will do whatever you need to ensure they are completely taken care of!

Sitter Profile Image: Tanika L.
Verified Enhanced Background Check
Tanika L.
from
$20
per visit
5.0 out of 5 stars
16 reviews
4 repeat clients
12 years of experience
Richmond, KY, 40475

I recently moved from NY to KY and was in need of someone to help care for my four dogs. I had spoken to many people and wasn’t comfortable with anyone as I had my prior dog walker in Ny for over 10 years. I found Tanika and she and I hit it off right away: she was super accommodating to my ever changing schedule. I was nervous to have my one rescue dog meet anyone because he could be unpredictable. Tanika came armed with treats and was relaxed and so easy going with all the dogs that he took to her first!!!! Tanika had been above and beyond amazing . She helps with my dogs that have medical issues and she is always there when and if I need her. She takes care of my dogs as if they were her own and I’ve never had to worry about them when I’m away. She is an absolute god send and I highly recommend her!

Profile image
Kimberleigh M.
Sitter Profile Image: Mia R.
Verified Enhanced Background Check
Mia R.
from
$13
per visit
5 years of experience
Richmond, KY, 40475

About: With your pets permission, they will be loved on. Pets in my care will be treated like family. I have been around pets of all kinds my whole life and have pet sat for over 5 years! The only days of the week where I’m out for more than 3 hours is Tuesdays and Thursdays. I am at home otherwise, the more time I have with your pet, the better! I do have two cats, so they will likely be separated from your pets in a boarding situation, but I live next to a dog park so it is easily accessible for pups. I have many cat toys and treat varieties as well.

Sitter Profile Image: Selah M.
Verified Background Check
Selah M.
from
$20
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Richmond, KY, 40475

Selah did a fantastic job. This was our first time using rover and she did not disappoint. She kept me well informed of messes, updates and earned our dogs trust. She even picked up our trash cans when the wind blew them over. Highly recommend using her to care for your fur baby.

Profile image
Kaitlyn W.
Sitter Profile Image: Emily L.
Verified Background Check
Emily L.
from
$25
per visit
5.0 out of 5 stars
94 reviews
42 repeat clients
15 years of experience
McKee, KY, 40447

Emily was wonderful and played with our pup!! Will use her again in the future. Very flexible with schedule and reads the what the dog needs during the visit!

Profile image
Brittany R.
Sitter Profile Image: Brittney J.
Verified Enhanced Background Check
Brittney J.
from
$20
per visit
30 years of experience
Richmond, KY, 40475

About: What sets me apart from other sitters is my patience, attention to detail, and genuine love for animals of all personalities. I have two labs and two cats of my own, including a rescue we welcomed into our home, so I understand how important trust, routine, and a calm environment are for pets. I successfully introduced all of our animals and helped them learn to coexist comfortably, which gave me valuable experience with animal behavior, slow introductions, and reading body language. I’m comfortable caring for both energetic and anxious pets, and I take pride in making animals feel safe, loved, and relaxed while their owners are away. I also genuinely enjoy the little things that make a difference — keeping spaces clean, deep-cleaning litter boxes, sticking to routines, and giving pets individualized attention based on their needs and personalities. 🐾 Pet care is already a huge part of my daily life, so caring for other animals fits naturally into my routine. Between my two labs and two cats, I’m used to managing feeding schedules, walks, playtime, cleaning, and making sure each pet gets individual attention and affection every day. I genuinely enjoy spending time with animals, so pet care never feels like a chore to me — it’s something that brings me peace and happiness. I’m someone who pays attention to the little details, whether that’s noticing changes in behavior, keeping litter boxes and living spaces clean, or helping pets feel comfortable and safe in their own environment. My schedule allows me to be dependable, communicative, and consistent with the care I provide, which I know is important when someone is trusting me with a beloved pet.

Sitter Profile Image: Alexrandra H.
Verified Enhanced Background Check
Alexrandra H.
from
$17
per visit
9 years of experience
Mckee, KY, 40447

About: I have experience with puppy training basics, including house training reinforcement, crate training, leash manners, and maintaining consistent routines. I’m patient, calm, and positive, which helps young dogs learn while feeling safe and confident. For senior pets, I provide attentive, compassionate care, including administering medications, assisting with mobility, sticking to specialized diets, and monitoring for any changes in behavior or health. I understand that older pets need extra patience and gentle handling, and I make their comfort a top priority. Above all, I treat every pet as if they were my own—providing reliable, loving, and trustworthy care while keeping owners updated and worry-free. I am currently staying at home due to a lapse in full time work! Taking care of my pets is naturally in my daily routine as well as working on commission based art work. When it comes to taking care of pets in home, I am able to safely separate them from my other pets if need be. All of my pets are vaccinated! I do not have a fenced in yard, however I do have a gated porch! If your pups need walked they will be safely walked on a leash or they can be placed in my outside kennel if requested by you! :) pets are allowed on furniture!

Sitter Profile Image: Allison K.
Verified Background Check
Allison K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
38 reviews
11 repeat clients
10 years of experience
Stanford, KY, 40484

She was awesome! Took care of both my dogs on a holiday with a last minute booking after I had some things come up. Would definitely recommend!

Profile image
Blake F.
Sitter Profile Image: Debra A.
Verified Enhanced Background Check
Debra A.
from
$35
per visit
5.0 out of 5 stars
10 reviews
4 repeat clients
20 years of experience
Lexington, KY, 40517

About: We work from home full-time, which means your pup will get lots of supervision, attention, companionship, and cuddles throughout the day instead of being left alone for long periods. Dogs staying with us typically get up to two walks a day, usually 1–2.5 mile walks at nearby trails. If your pup enjoys walks and adventures, they’re welcome to join! We also make sure dogs have plenty of supervised playtime, enrichment, rest, and individualized attention depending on their personality and energy level. We genuinely love pets and try to make them feel like part of the family while they’re here. Whether your dog is playful, cuddly, shy, energetic, or prefers a calmer environment, we do our best to adapt to their needs and routine. We're also happy to provide regular updates, photos, and videos so you can feel comfortable while you’re away. We know how important it is to trust the person caring for your pet, and we aim to create a safe, loving environment where both you and your pup feel comfortable. I have a flexible schedule to give your pets the love and attention they deserve! I take my dog on walks twice a day for 1-2.5 miles in the park and typically spend the rest of the day at home, treating your babies like my own. I have a fenced yard and live walking distance from a park with wooded trails. I have a friendly pup in my home who loves having friends to play with. I will care for your pets like my own!

1 / 1
View more sitters

Winston pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Alicia is dependable, professional and my cats’ best friend. She has made it possible for us to leave home and know that our cats are going to receive the same attention as we give. They literally greet her as if she has never left!

Profile image
Diana F.
Drop-In Visits
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Winston pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available 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

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.