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

Over 56 pet parents in Winchester have booked pet sitting
Winchester, 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.

“I highly recommend Jessica! Jessica does a wonderful job caring for pets! She videos her visits and keeps the owner posted in a timely manner. My quirky dogs enjoyed her visits so much! She provided scheduled medications and feedings and potty breaks as requested during stormy weather and hectic holiday schedules! How wonderful to be able to have our pets at home with someone so professional and reliable! We will call on her again”

About: Through my life I have experienced taking care of family pets, from the puppy stage to crossing the rainbow bridge. I often think I love animals more than people. I am currently working from home part time with flexible hours, so I can play with and cuddle your fur babies as much as they want. I can board, pet sit or just walk your dog weekdays or weekends day or night. I have a fenced in yard with one senior dog. I can crate a dog up to 40lbs. We can go for walks if desired.
“Ashley was great!! I got pictures & a report card every check-in. She was very attuned to my senior kitty. She is on some medication that can come with side effects and Ashley made sure to let me know what she was noticing! Definitely will hire again. She has a great attitude & even watered my plant while I was away! Thank you so much, Ashley!!”

“Susan took such great care of my little fur baby while I was away for the holidays. She kept me updated with her visits and I knew my little Kiwi was in a great, loving hands while I was gone. I highly recommend Susan if you want someone who truly loves dogs and who'll care for them like they're her own. I will be using Susan to car for my fur baby whenever I need to travel.”
About: I’ve had cats my whole life and love everything about them! I’ve cared for kittens, adults, seniors, and multiple pet households. I have experience with post-op care, cat introductions, and indoor/outdoor cats. I also have experience taking care of young and senior dogs, including administering medication and interacting with cats. Housesitting - I can’t be there 24 hours a day because I have my own pets, but we can discuss how much I need to be away. I work full time from home, mostly available evenings and weekends, daytime if my schedule allows. I’m a night owl so late night visits are okay! I go at your pet’s pace and provide a safe, loving environment so they gain my trust. I go by their usual routine/ habits as not disrupt their routine.
About: Hi! I’m Renata, and I treat every dog as if they were my own. I make sure they feel safe, happy, and loved at all times. I pay close attention to their needs, give lots of affection, and provide walks or playtime to keep them active and joyful. Your dog will also enjoy my large backyard, perfect for running, playing, and exploring safely. Whether it’s boarding in my home or daily walks, your dog will feel comfortable, cared for, and truly at home. I can’t wait to meet your furry friend! I’m available to care for your furry friend in the afternoons and evenings starting at 4:30 PM on Mondays, Tuesdays, Thursdays, Fridays, and Saturdays. I’m free all day on Wednesdays and Sundays, so I can give your dog plenty of attention and playtime! My home is a safe and secure environment for dogs. I have a large backyard where your furry friend can run, play, and explore safely. I also have a 7-year-old Pug who is very calm, enjoys socializing with other dogs, and respects their space. I make sure every dog feels comfortable and confident while in my care, giving them love, attention, and plenty of supervision at all times.
About: I am a very pet-oriented person, having had cats and dogs in my life since I was small. I am empathetic to when pets need extra reassurance and attention, and go the extra mile to make sure my furry friends feel comfortable and well cared for! I'm always available to answer any questions or concerns, and am independently insured outside of the Rover Guarantee. I am currently working part time which enables me with a lot of flexibility and free time to meet your pet care needs. Chances are great I will be able to accommodate your pet visit or pet sitting schedule needs so feel free to reach out and let's get acquainted! I prefer to care for pets in their regular home space to limit their stress. I will be careful to follow all instructions and prefer written instructions for pet care and any light home care needs you have.
About: I found my own dog for over 10 years. My previous job was at a doggy daycare. I am time oriented and affectionate under my care. I will be open and free on rotating weekends. I am typically off Monday & Thursday. I do have a day job from 8am-4:30 in Creve Cour. I can consider any other days if needed. I have a flexible schedule under communication to help care for your loved pets. Give me a call and we can talk in messaging and meet in person. I will keep tidy of the clients home. I will provide a safety net to all who is under my care. Daily updates if needed.
“Our normal sitter had a family emergency right before the holidays, and we are so thankful we found Kate in time for our kitties! Two of them need daily medications, and we have had hit or miss luck with different sitters (not from Rover) in the past, but all the cats loved her (even the one that normally hides!) and they all seem to be very relaxed and not panicked when we got home this time! We will absolutely be using her in the future and recommending her to friends in the area!”

About: I really enjoy spending time with furry friends and provide a lot of attention and care to them. I am attentive to their behavior and emotional state and communicate everything to owners immediately. My perfect fit would be mature dogs with moderate to low energy levels, that are quiet and like to cuddle. I don't do well with highly anxious dogs but can provide a good level of support to slightly/moderately anxious dogs. I can provide regular exercise in a form of the walk as often as needed but am unable to take the doggy out more often than every 3 hours. About me: I'm quiet, responsible, and easygoing. Don't have visitors often. I like to draw, do something crafty and read! Prefer a quiet environment. My parents live with me too. My dad works full time, but my mom is almost always home. I'm have flexible schedule and often work at home, so your pet won't be left alone very often. And if we do need to leave, it would only be a few hours and I would mention it to the owners to make sure it is okay. I can provide potty breaks every 3-4 hours but prefer dogs that can stay alone without potty break for 4-6 hours just in case. I will do what I can to accommodate your pet's needs! We have double door and I usually a bit anxious about safety and concern about dogs running away. I will also make sure there is nothing unsafe on the floors before pup arrives.

About: I've lived with dogs my entire life and have never met a dog I can't connect with. I love dogs of all sizes and behaviors; I have experience counseling groups of kids at summer camp, so I have no trouble managing dogs in a group or with rowdy tendencies. I truly love all dogs and would love to meet yours! I am currently working part-time in St. Louis on the weekends, so I am available weekdays at any time. I have access to a car and the ability to be flexible with timing and distance as well, just contact me! I can work with any number and any kind of dog! I grew up with a couple dogs of different sizes and I currently live with 2 little ones, so I am comfortable handling any canine situation! This means I am more than happy to take on any responsibility/task requested, such as administering medication, engaging in frequent or constant activity, intently monitoring an animal for an extended period of time, etc. beyond, of course, walking & relieving your best friend(s)! I will always provide dilligent and careful care of both your pets and your home.
About: I’ve cared for pets of all ages, from playful puppies to gentle seniors. I provide patient, reliable care and treat every pet like family, ensuring comfort, safety, and love. I work from home everyday of the week except Wednesdays so I have a very flexible schedule to take care of if your pets! On Wednesdays I am usually home before 2pm so your pet would not be left alone for long periods of time ever. Your pet’s safety always comes first. I provide a clean, calm environment, fresh water, supervision, and plenty of love so they feel secure and happy.

About: I have hundreds of services completed with excellent reviews on another platform and am taking my skills and experience to this one. I've always had dogs and always connected with animals, and friends and family have recognized that affinity and felt comfortable and trusting their fur babies to my care over the years. I've worked with shy dogs, anxious dogs, aging dogs, dogs with high medical needs, puppies, power breed dogs, tiny dogs, and pretty much any other kind you can imagine. I'm looking forward to giving your pet the same high level of care! I have a flexible schedule that I control, so I have a lot of availability to help you care for your pets. I don't even mind the early morning or late evening walks! I have many regular clients, and they tend to pick me when they need someone reliable (to care for their pets when they're away, to show up on time for a 6am walk before an important procedure, to care for a dog who needs extra patience or care for medical needs, etc.). I was a store assistant manager for 15 years, so I know how to keep calm in emergency situations and understand the responsibility of having people who are relying on me. I also have a musical background, so I'll probably end up singing to your animals like a Disney princess at some point.
About: Hi, I’m Brie! I’ve cared for dogs of all sizes—from volunteering as a dog walker at the APA shelter to sitting for friends, family, and neighbors. I’m also a college cross country and track athlete, so I love running with high-energy pups who need more than just a stroll. Whether it’s playtime, long walks, or snuggles, I tailor care to each dog’s personality. With two dogs of my own, I know how important it is to find someone reliable, active, and loving. Your dog will be treated like family! Weekdays: Dog walking & drop-in visits Weekends: Overnight sitting & extended care Winter & Summer Breaks: Open availability for sitting, walking, and extended care Also available in Webster Groves Your dog’s wellbeing is my top priority. I create a calm, secure environment where pups feel at ease—whether we’re out for a walk or relaxing at home. I follow your care instructions closely, keep routines consistent, and always prioritize safety on walks and during play. With years of experience and two dogs of my own, I understand how important trust is. I treat every dog like family, offering gentle guidance, positive reinforcement, and a space where they can thrive physically and emotionally

“Barbara did a great job taking care of my boys (cats) while I was away. She showed up as scheduled and took care of feeding and cleaning the litter boxes. I got photos each day which was fun to see and a video one day as well. Nice to know that they were well taken care of!!!”
“Keirra is simply astounding! She is incredibly attentive to your pets needs as well as your own, and Is very clear on her Rover cards about how they are doing. She spends quality time with your pets and makes sure not just food and water, but things like pet cameras are operating so you can see them! She gets back to messages promptly and was flexible when my transportation was canceled and needing rescheduling. I highly recommend this amazing sitter!”

“Madyson felt like family the moment we met, I knew she’d take great care of my lil guy 🥰 expectations exceeded! This was my first time using the sitting service and I’ll definitely do it again thanks to her.”

The median cost per visit for pet sitting in Winchester is $20
Pet parents share their Rover experiences - Winchester
Ashley was absolutely wonderful! She took great care of my boys while I was out of town. She kept me updated throughout my trip and sent lots of pictures, which gave me peace of mind knowing they were in good hands. She was reliable, attentive, and clearly cared about my dogs. I would absolutely book with her again and highly recommend her!

⭐⭐⭐⭐⭐ The BEST Rover sitter! Emily is truly such a blessing to us, and I cannot say enough amazing things about her! ❤️ She is the sweetest, most caring person, and it is so obvious how much she genuinely loves and cares for Thea. She treats Thea like one of her own dogs, and that means more to me than she will ever know. Emily goes above and beyond every single time she watches Thea. She brings her special treats and bones, takes her on walks, and even puts on Paw Patrol or a movie for her to watch while I’m away. 🥹 It’s all the little extra things she does that show just how much she cares. Knowing Thea is not only safe but also loved, spoiled, and happy while I’m at work gives me such peace of mind. As someone who has to be away from home for long shifts, having someone I can trust with my girl is priceless. Emily is so much more than a dog sitter to us. She is a huge blessing in our lives, and I feel so lucky to have found her. I would recommend her a million times over to anyone looking for someone who will love their pet like family. Thea and I absolutely adore her! 🐾💕

Cleo was wonderful with my kitties and they adore her! One of them is very shy and hid at first, and she took the time and patience to make him feel comfy and made sure he got what he needed. She was communicative about how they were doing and I felt so much better being away from them knowing she was there and loving them like her own cats! She is awesome and we'd happily book her again!!

Ashley was great!! I got pictures & a report card every check-in. She was very attuned to my senior kitty. She is on some medication that can come with side effects and Ashley made sure to let me know what she was noticing! Definitely will hire again. She has a great attitude & even watered my plant while I was away! Thank you so much, Ashley!!

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 - Winchester
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winchester average 7 repeat pet sitting clients
FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
The average cost of Pet Sitting in Winchester is $17 per visit as of November 2026. Most bookings cost between $13 and $28 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 2,702 sitters on Rover offering Pet Sitting across Winchester. 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 Winchester. On Rover:
- 89% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% 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.















