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.
“Amy is an outstanding person and pet sitter. My puppy is so happy to have her come by for her visits. She is timely with communication, pleasant, and she takes exceptional care of my pet. I really appreciated her flexibility and attention to detail.”
“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!!”
About: Hi! I’m a local mom, animal lover, and lifelong dog enthusiast! 🐾❤️ Our family sadly lost our sweet dog this summer, and while our hearts aren’t quite ready to welcome a new puppy of our own, we have so much love left to give! I would absolutely love the opportunity to care for yours! I’m offering dog walking, pet sitting, and check-in services for busy families, working professionals, or anyone who needs an extra helping hand with their furry family members. Whether your pup needs a neighborhood walk, a potty break, some playtime, or a loving place to stay while you’re away, I’d love to help! I know firsthand that pets are family, and I promise to treat yours with the same love, attention, and care that I would my own. I can’t wait to meet your four-legged family members! 🐶💕 I have a very flexible schedule for the most part. I am a real estate agent and a mom to twin boys who are in school full time. I can easily pop over to your home or have your dog to our house as well. My yard is almost completely fenced in except for our driveway. I’m happy to take your dog on walks as well. I am happy to let your dog run free inside at our home or crate. Whatever makes you feel comfortable.
“Liana was great as usual. She takes great care of our cats when we need her. There was a slight hiccup getting into the home while we were gone, but she was in constant communication with us and made sure that she could take care of our kitties! We will absolutely have her care for them again and would highly recommend her to others! Thank you so much Liana!!!!”
“Blanca was an amazing caregiver to our two dogs while we were in Hawaii. She kept us updated with pictures and videos of them playing, chasing the ball, enjoying pets and scratches. We would definitely recommend Blanca and will 100% use her in the future!”
“Alexandria took great care of our kitties while we were out of town! We have some finicky eaters and one who needs meds, and she didn’t have any issues with them. She was also kind enough to take our garbage cans from the curb and get the mail. I would highly recommend her!!”
“Alli is excellent!!! Alli worked with us for 5 days straight, two times per day. She was on time 100% of the time and was excellent with our puppies. She took them for long walks and always asked if there was more she could do. Alli is very kind and easy to work with. She is also a good communicator. I highly recommend Alli and we will definitely have her back (often!)”
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.
About: I have always been drawn to dogs. Having grown up on horse stable, dogs were part of our lives. I've trained many puppies in potty training and currently work with rescue groups and have helped raise litters of puppies. Have worked with seniors, diabetic dogs and dogs with physical handicaps. My fenced-in, secure, back yard provides security and an opportunity to enjoy the outdoors. In the summer, the breeze and the shady trees make it a comfortable place, even on a hot day and my home is on a quiet cul-de-sac away from busy streets. I schedule between 8am and 6pm and ask for communication if you are running late. I am a LICENSED and INSURED provider as is a requirement in the state of Missouri. My dog park is a safe haven for fun and sun! Fully fenced-in backyard for their safety. Shady trees atop a hill at the end of a quiet cul-de-sac.
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
About: Nearly three decades experience Wide open availability Have worked with every breed/personality imaginable. Can adapt to any pets needs great or small. Have worked with all ages and medical needs. Medication, food sensitivities, and personal preferences are very important and will be treated with equal priority. I have a very open availability and no spouse or children. I prioritize the pets I'm caring for over other obligations and will be open about any scheduling conflicts. (but that's unlikely to happen) My service involves precise and personalized care depending on the pet's needs and personality. No two pets are the same and each needs to be understood according to their lifestyle.
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.
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