Pet Sitting Winesap
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Winesap, 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.
“Absolutely brilliant care from Jennifer. Extremely thorough, professional, and exceptionally compassionate care for my 3 dogs. She went above and beyond to make my pets (and us) feel comfortable & confident. Don’t think we could’ve asked for any better. Five Stars plus.”
About: Hi, I’m Zane. You might say I have a bit of a Lucky Dog mindset when it comes to working with pups. For years, I’ve helped dogs build trust, confidence, and joy through calm leadership, positive reinforcement, and plenty of tail-wagging fun. Now, I’m bringing that same heart and expertise to the trails, parks, and neighborhoods. What Makes Me Different? As a college student studying both psychology and animal science, I don’t just walk dogs—I connect with them. I understand dog behavior on a deeper level and use that knowledge to make every walk safe, structured, and enriching. Whether your pup is high-energy, shy, reactive, or just needs a steady hand, I’ve got the experience to make sure they feel secure and cared for. Every Walk is a Training Opportunity My calm and confident approach turns a daily walk into a moment of growth. I reinforce good leash manners, provide mental stimulation, and make sure every dog gets the physical exercise and emotional connection they need. Service You Can Count On • Tailored walks based on your dog’s energy level and personality • Consistent routines and detailed feedback after each visit • Clean, respectful home visits with plenty of play, affection, and fresh air • Trusted care with a trainer’s eye and a host’s heart Whether you’ve got a brand-new puppy or a wise old soul, I’m here to give your dog the kind of care that’s worthy of a spot on Lucky Dog—because every dog deserves that kind of attention. Let’s give your dog their best day, every day. Pet care fits really naturally into my daily routine. I have a flexible schedule, so I’m home often and can plan my day around walks, feedings, and playtime. I enjoy starting and ending the day with pets—it’s a great rhythm and honestly something I look forward to. Whether it’s sticking to their usual schedule or giving them extra love and attention throughout the day, I make pet care a priority and enjoy having it as a regular part of my week. Whether I’m watching pets in my home or theirs, I always make safety and comfort my top priority. I take time to understand each pet’s routine, needs, and personality so I can provide care that feels familiar and stress-free for them. In my home, I keep the space clean, pet-friendly, and secure—no access to anything unsafe, and always supervised during play or outside time. If I’m caring for pets in their home, I stick closely to their regular schedule and make sure they feel at ease while their family is away. I treat every pet like my own, with lots of love, attention, and respect for their unique habits and preferences.
“Amber was amazing! She took great care of my girl and she truly made her feel safe and loved while I was away. She handled everything so well and provided great care for my sweet girl. I got pictures, videos, and updates all within a timely manner. Would 100% recommend Amber to anyone!”
About: Growing up, my family had 3 dogs that we took care of. In college, I adopted a cat and have been taking care of her. I currently work full time right now however my weekends are typically freed up. I can stop by for a drop-in visit twice a day. Can make sure you pet is crated if needed and walk them as well! I can drop in and feed and play with them also.
About: I used to have a pug and a small teacup Chihuahua and I loved them with all of my heart sadly we had to get rid because me and my mom were moving out of our old town house Im currently working a part time job at Kroger and I go to work at a cardboard factory at a building called achieve so weekends and week day availability really depends on how many days I need to request off I live with 2 dogs Charles and sady one is a German shepherd mix and Charles is a mini poodle we have a fenced in back yard and let them out to go to the bathroom and go for walks I love sady and charles
About: Hi! I’m Jamerson, a caring, dependable, and attentive pet lover who understands how important it is to feel comfortable with the person caring for your pet. I’m happy to provide walks, drop-ins, playtime, feeding, and companionship while keeping your pet’s routine and comfort a priority. I’ll treat your pet like family and keep you updated along the way! Reach out today, you’ll love my service. I have open availability at the moment. Pick a date and time and I’ll be there. Looking forward to taking care of your animals and or home. Not applicable. I do not care for animals in my home being that I have two animals already. I am able to go to your home and walk your dog in your neighborhood.
About: I have six years of experience caring for dogs, including my own and pets belonging to friends and family. I’m dependable, patient, and comfortable following each dog’s individual routine. I can provide walks, feeding, playtime, bathroom breaks, and plenty of attention while keeping owners updated with photos. My background in behavior has also taught me to remain calm, observant, and consistent with every pet. I work Monday through Friday from 8 a.m. to 4 p.m., so I’m available for evening visits during the week and have more flexible availability on weekends. I’ll always confirm timing in advance to ensure your pet receives dependable, unrushed care. I will follow your cat’s normal routine and all care instructions closely. I’ll keep doors and windows secure, refresh food and water, clean the litter box, provide playtime or quiet companionship, and send regular photo updates after each visit.
About: I worked for an Animal Hospital for 4 years and am familiar with dogs of all breeds, sizes, and personalities. I have dealt with some of the happiest and most anxious dogs and cats so I am pretty comfortable with anything. Will also give medication if your pet requires it. I have 2 dogs of my own who are very high energy, so I am used to that as well. I also deal with puppies and elderly dogs everyday so age is no issue. I don't mind any breeds! Small caged animals, fish, or some outside animals are no problem either. I hope you will choose me to check on your babies while you may be working or out of town for a while! Thank you so much guys! It will definitely depend on day and time but I am pretty flexible! I don't work quite as much as I used to but I do still work full time. I go by and do what I am told by the pet owner to keep the babies in routine as much as possible so they do not become stressed but with that being said I also am not able to stay all day or neccesarily the exact times you might due to also having a work schedule to abide by.
About: I have taken care of animals of all shapes and sizes my entire life. I grew up with at least two large dogs at all times, and at points there were four of them in the house along with birds and copious amounts of cats to take care of. I also have experience caring for large animals such as horses and I have eight years of handling them under my belt. Along with all of this, I also have experience in giving both medications and insulin shots to both felines and canines. I am currently working a full-time job at the Lynchburg Humane Society. I have availability in the mornings, middle of the day, and evenings to care for little critters! This would include walking, potty breaks, and caring for them however they need! I currently have two dogs who have a big double fenced in yard to play in, but would only have your furry friends interact with my animals if there were to be an emergency. I would be able to easily crate your pet and do whatever is needed to keep them safe and comfortable!
About: I have had animals all my life and currently have the most perfect pets at home, a 100lb yellow lab named Max and two cats, Skippy and Toulouse. I am comfortable giving medication and have experience with diabetic dogs and cats. I can play with your pet, take them for walks, or just give them company while you're away. I look forward to meeting you and your pet! I am able to work during breaks from university, largely including Christmas break and summers. I would be able to watch your during the week or on weekends, but I will be unavailable on holidays (Christmas Eve, Christmas Day, etc.). I cannot watch pets at my home, but would love to look after them in an environment they are familiar with, your home. :) All potential jobs will be determined after a consideration of location, time commitment, and my availability.
“Mia was amazing. She is very professional and kept me updated throughout the time I was gone. She wanted to know everything about Loki and took notes to be on top of things over the weekend I had her dog sit. I strongly suggest first-time customers book with her if you want a completely stress free booking. I will 100% go with Mia the next time I need a dog sitter, knowing not only I, but my dog Loki, will have a pleasant experience.”
“Casey did a wonderful job of caring for our three kitties while we were away for a week. Casey is very dependable and trustworthy. She did a great job of communicating with us while we were away. I highly recommend her services!”
“Samantha was great. I just needed someone to drop by and check on my kitties. She was great at communicating with me and sending me pictures. I would totally hire her again. ?”
“⭐️⭐️⭐️⭐️⭐️ Gillian is AMAZING. This was my first (and second) time using Rover as we could not bring our pet Tiger with us. I am always worried to leave him bc he is extremely shy and skittish. Nonetheless, Gillian gave me so much peace of mind posting pictures to Rover daily. I genuinely looked forward to the updates each day. Her attention to detail, open communication, and loving care for animals is evident. She exceeded my expectations BOTH times and I was over the moon 🤩 My husband and I truly didn’t need to worry while we were away. After the first booking, we knew Tiger was in good hands and wanted to book with Gillian again 🐾💙 We are SOO thankful to be able to trust her in our home and with our shy fur baby. Book her, you won’t regret it. Gillian is the best!!”
About: Quiet Country setting for your pet. My husband and I have taken care of dogs and cats since we were around 10 years old. We have helped with various breeds and sizes. From as small as chihuahua and pug, up to shepherds and Labrador retrievers. We currently have two dogs of our own that we adore! We treat all dogs like they are our children. My husband and myself are currently full time at home 7 days a week so can provide attention and care like we do with our pets . We work from home so we are able to give full attention since we work from home during the week. We can provide daily walks, and playtime either outside or inside. Our dogs can keep your pet company they love all dogs and cats. They will have the comfort of cuddling on pet pillows or even cuddling on the couch with us. My husband and myself are full time at home to be able to provide the needed time to care for your pet. Only be alone few hours on weekend to run errands We can offer daily exercise like walks on a leash due we have a nice big yard but do not have a fenced in yard. Also could crate if needed. At client's home would provide exercise, play time, and crate if needed.
“Crystal was quick to respond and get booking details confirmed, though I made it on short notice. Very communicative during when I was gone. An absolute delight to work with. Plan on booking with her again.”
The median cost per visit for pet sitting in Winesap is $19
Pet parents share their Rover experiences - Winesap
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 - Winesap
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winesap average 5 repeat pet sitting clients
FAQs for Pet Sitting - Winesap
Frequently asked questions about Rover
As of November 2026, there are 314 sitters on Rover offering Pet Sitting across Winesap. 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 Winesap. On Rover:
- 89% of sitters can help with special care needs
- 94% 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.
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.
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