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 527 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 am beyond grateful for the care Ashley provided for my elderly dog while I was away. I was in a bind last minute, and she was available on such short notice, which immediately put me at ease. She was incredibly responsive, provided consistent updates, and treated my dog with so much patience and care. Knowing my senior pup was in trustworthy and reliable hands made my vacation completely stress-free. I would absolutely recommend her to anyone looking for a dependable and compassionate pet sitter, especially for older dogs.”
About: My whole life I grew up with dogs. I will love your pet as one of my own. I am available for dog walks and trips to the park. Feedings when you are unable to make it home and just to give your Dog that extra loving every dog needs. I have two of my own with different personalities so I am not surprised of anything. I am your girl for your Dog needs even for a quick play date with my dogs. I have taken care of dogs from puppy stage to elderly stage. I know what it takes to potty train a pup and how much work it is. Please take me into consideration and I can’t wait to hear from and meet you pups I have Friday to Sunday off which is perfect for a weekend getaway as well as I get off work at 330p Monday to Thursday providing afternoon walks. I will follow any of the rules you provide. I know animals can be escape artist and I will treat your pet as my own
“Brandee was awesome, we went on a 12 day vacation! She went above and beyond to make sure Princess and my house was safe and kept in good condition!! I will definitely be using Brandee again for Princess on my future vacations. Thanks again!!”
About: I’ve worked with dogs since I was 13. Weather it’s been working with new puppies or elderly pets I’ve seen it. Doing day to day walking and pet sitting. I take care of the pets so they can stay on a schedule. I’m currently a student at UNLV, but my schedule allows for plenty of time to be around, walk, and play with your pets through the day. I care for pets in their own home by following the same routine as the owner. Feeding on schedule, refreshing water, handling walks, and bathroom breaks. Keeping their environment clean and safe with plenty of attention.
“Michelle took great care of our senior dog! Took her on several walks, even in the rain and spoiled her like family. We truly appreciate her and will certainly use her again!”
About: I've taken care of homes and animals since I was a young girl in East Texas. I love animals and think every being needs love and affection to thrive. Walking dogs is my favorite hobby! I work remotely as a Customer Success Manager, which allows me to have a flexible schedule to accommodate my passion to help people in my community, and especially those with pets! With your instructions followed precisely, I will provide the service purchased, with the love and respect for your pet and property, ensuring your upmost satisfaction.
About: I grew up with animals from dogs to guinea pigs. I have experience with owning and caring for a pet. I have the space and recourses to board or pet sit. I would love to care for your fur baby. I am free during day all week. I have an open schedule Saturday, Sunday and Monday. I have time to care for pets whether it is giving scheduled medications or just to be walked and played with. My backyard is completely closed with concrete wall. I do allow pets in my house. The pet will have easy access in and out of the house.
“Kim did a fantastic job with Kira on her drop-in visit! We had had a meet and greet many weeks ago for a booking that I ultimately had to cancel, but Kira remembered Kim when she walked through the door, which says a lot about Kim's energy. She let Kira out, fed her, and played with her. She also sent some really cute pics! Kira's a fan now, and we'll definitely be rebooking with Kim in the future. Thank you for taking care of my girl!”
“I’ve been using Mariana to walk and check in on Winston since November and she’s always been on time and loving with him. If she’s running late or needs to make a schedule change, she’s very communicative and flexible. I trust her with my fur baby and I know he loves her and enjoys spending time with her when she comes by. I look forward to continue using her services for as long as I can!”
About: I’ve taken care of my dogs of all breeds since I was thirteen years old. My family have relied on me to take care of their pets by walking, feeding, and bathing them. I have plenty of schedule are open! I always love takes cares with your dog at my house everyday! I’m open on everyday but available for evenings and some morning. I always safe dogs or cats in crates all time. I know do put crates all time. I always check on them everyday or anytime.
About: I have a 10 year old yorkie named princess and have always loved and cared for animals especially dogs. I love taking care of them I am open and available all week and all hours of the day and can board and walk your dog anytime. No matter what day or time I make sure they are taken for walks and make sure they have water food and play fetch and make sure they are comfortable in their environment
“"Ana was wonderful! She looked after my elderly cocker spaniel and my blind standard poodle for the last two days. She was punctual, provided great updates, and made sure all medications were administered correctly. Both dogs seemed so much happier when I got home. Highly recommend her services!"”
About: Pet parents and lovers! We use Rover for our pets when needed, so we understand the importance of finding someone who is trustworthy, reliable, and responsible, but also someone who can make your pet feel a little less alone when you are away. Let us be the break your pet needs throughout the day! We do walks, dog parks, stop-in visits, brief home visits, or longer stays (up to two weeks - and at our place only please). We also do baths, play time (obviously!), and errands. We can also follow any training techniques in place. I’m self employed, running a nonprofit that serves veterans and first responders. We advocate and bring awareness to suicide prevention and mental health initiatives. Since I’m self employed, and given the nature of the daily operations pertaining to my job, I have flexibility. Our “dog proof” home comes with a large, fenced in backyard. We have a doggie pool, all basic dog supplies, dog training supplies, all basic cat supplies, leashes, etc. If we are traveling to your home, we suggest that you send us clear, step-by-step instructions and any expectations you may have, and trust that we will exceed your expectations. We genuinely just love animals and want to help out other pet owners while making a little cash.
“Very accountable with photos. My puppy looks very happy and Andrew is more than accommodating. Thanks so much. Mozzie can’t wait to have weekly walks with you”
“Anna is very caring and attentive to our little pup. She shows up on time and gives our pup her full attention. We couldn’t have potty trained our pup without her help, since my partner and I have work during the day. Highly recommend!”
About: I have had dogs & cats my whole life! I can't imagine not taking care of a dog or cat! I'll never let any harm come to your pets! When your pets aren’t playing in my backyard, swimming in my pool, or doing their business they will have one of the guest rooms in my house to chill. Meet Ethel – Our Official Boarding Hostess 🐶 After I retired in June 2023, I began boarding and walking dogs through Rover and Wag. What I didn’t expect was to end up with a 50/50 business partner. Ethel joined my life officially on January 2, 2025, after boarding with me several times throughout 2024. She quickly proved herself to be calm, confident, and remarkably good at managing group dynamics. A few days after she moved in, I discovered something extraordinary: Ethel was born on my 58th birthday—the very morning I was out walking a dog named Cuda. Since then, Ethel has become the heart of my home-based boarding setup. She’s the official hostess, a natural leader during playtime, and the quiet enforcer of naptime. Boarding runs smoother with her here—less chaos, better routines, and happier dogs all around. Think of her as the technical advisor for playtime logistics… and my most valuable coworker. I will follow their owner’s exact specifications. As long as it is safe and healthy for the dog or cat, I'll follow the owner's directions verbatim! I have always fed my dogs and cats Science Diet pet food!
“My three dogs are always happy and relaxed when I come home, there is no big drama of us being away. To me this signifies that Brenda is doing an excellent job of caring for my dogs. They enjoyed her company and the photos she provides us, are great. They're always happy. I would trust Brenda with all my pets all the time.”
“Ariana was great and very communicative. We were looking for in-home drop in visits on short notice and were lucky to find her. She was willing to come by for a meet and greet prior to our departure which was super helpful in making sure our dog was comfortable and saw a familiar face while we were gone. We will likely be utilizing Ariana as a sitter again!”
“To anyone considering booking Josh, just do yourself a favor and do it right now! This was our first time using a pet sitter, and we were quite nervous about the process, but Josh was very kind throughout the journey. We were updated consistently throughout each check in. He was kind, patient, and caring with our dogs, and not only cared for our dogs but went above and beyond with helping us other ways in our house. We will definitely be rebooking him, and I know our dogs will be more than ecstatic to see him again!”
The median cost per visit for pet sitting in Winchester is $20
Pet parents share their Rover experiences - Winchester
Debbie is a wonderful sitter. The dogs love her and they are in very good, loving hands, with her. She is punctual and great about checking in during/after each visit. I definitely recommend her for families looking to find a caring and reliable sitter who your pets will really love; we look forward to working with her in the near future. Thanks again!
Jennifer is kind and very professional. She not only took care of my senior cat’s twice daily oral syringe doses, she described her method to me that is way less stressful for both my cat and me! She’s also very clean - she made a point of showing me the rinsed syringes, kept their dishes sanitary and their eating space tidy. She also respected boundaries and went out of her way to help with a side task I requested. I also needed to adjust the scheduling last minute and she was very understanding and cheerful about the inconvenience. Jennifer will definitely be my go-to sitter for as long as she’s available!
Cannot recommend Adam enough. Friendly, professional, and a clear animal lover. We have two cats who aren’t usually friendly to new people, and I work from home so they’re not used to being in an empty house. We were surprised how quickly they warmed up to Adam during his visits, and honestly they seemed disappointed when we came back!
Absolutely amazing cat sitter — could not recommend Liyuan more highly! Liyuan took exceptional care of my cat, Lottie, and I truly could not have asked for a better sitter. From the very beginning, she was thoughtful, responsible, and incredibly attentive. She treated Lottie not just as a pet, but as her own baby — with genuine care, patience, and affection.
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 $21 per visit as of November 2026. Most bookings cost between $12 and $33 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 2,557 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:
- 90% of sitters can help with special care needs
- 93% 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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