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 35 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.
âDella took excellent care of our 5 cats over the Thanksgiving holiday so we could visit out of town family without worrying about them. Have always had very good service from her.â
âKristen was willing to take on our very, VERY anxious dog without hesitation. Considering how challenging Otis can be, I know "average" pets would do wonderfully with Kristen and she truly loves taking care of pets.â
About: Our home has always been filled with dogs and cats. The strays find me and know they will always have a spacial place to call their own. I own a small consulting business and have flexibility with my schedule. I am easing into early retirement and looking to share my love of animals. I am an experienced professional who is phasing into early retirement. I have spent years traveling and have an empathy for pet parents who have to leave their fur babies while away from home.
About: Iâve grown up with dogs my whole life and love caring for them! Experienced with feeding, watering, walks, potty breaks, and ensuring pets are happy, safe, and well cared for. I currently have a very flexible schedule and am looking to take on as many pet care opportunities as possible. I am available most days of the week, with Sundays reserved for church. Iâm happy to work with a variety of schedules and look forward to helping care for your pets! When caring for pets in a clientâs home, I make it a priority to keep both the home and pets safe and well cared for. I will responsibly feed, water, walk, and play with your pets while following any instructions you provide. I am also respectful of your home and will help keep it clean, lock doors, turn off lights when needed, and ensure everything is secure before I leave.
About: I am friends and families go to dog sitter for when there is vacations, or someone is busy. I have been doing this for family and friends for a couple of years now im currently college student and would love to watch over your fur babies! with me being in school and work iâm normally pretty flexible with my schedule as all my classes are early in the morning! I have a huge fence around my yard and two adorable fur babies if yours are needing some company. I will be able to watch over your dog at all times if needed.
âExcellent Rover sitter! Josue did a wonderful job caring for our Goldendoodle. Responsible, reliable, and trustworthy! I highly recommend scheduling Josue as your next Rover sitter.â
âJenna is awesome and this my 2nd time booking with her. She takes wonderful care of my dog, is a great communicator, promt, and feel very comfortable leaving my dog in her care! I'm so lucky to have found her and absolutely recommend her.â
About: Iâve taken care of & had animals since I was about 10, and would love to help whoever needs assistance. Whether that be puppies or seniors, I am here to help. I can work any day Monday through Friday, and some weekends depending on the schedule. Mornings and afternoons are preferred, but am willing to accommodate to certain needs. We do not own any current pets at the moment, but have a fenced in yard with room to run around. I can accommodate to certain needs.
âGabby did awesome, we've used her for years, glad to see shes stretching her arms and joining rover! Our dogs love her to death and she is great with them. All 3 are pitbulls and she has no issues Keeping them spoiled and happy! Would book her anytime ! A very responsible and respectful young woman .â
âChristina is amazing! This was our first time with Christina and we hit a home run. She went above and beyond to care for our babies, as well as, helping us out with things we didnât even expect. She vacuumed up cat litter, collected our mail and took the trash out just so we wouldnât have to do those things when we got home. And as wonderful as all that is, her care of our Tootie and JP was excellent! She spent lots of time on walks and play time and it was obvious our babies loved her visits and looked forward to them every day. I highly recommend Christina to take care of your pets. Youâll be glad you did.â
About: My name is Luke, I am a CATCH Canine Trainer Academy certified dog trainer. I use positive reinforcement to encourage and maintain behaviors. I have always had a passion for working with dogs but after losing one of my rescues to cancer only 2 months after saving her my passion grew. This had inspired me to help owners and their dogs learn and grow together. I am a Co owner of a food truck which we are only operating part time. On the opposite days I have open availability to help support you and your current fur baby. I am unable to offer boarding for animals at this time. I am certified in pet cpr and first aid through ProPetHero by Pro Trainings
âShelby was great! She took most excellent care of Sophia and the Dew while we were out of town. She really cares, and we enjoyed getting the pics from her care visits, we would def use her talents again.â
âMelanie did a great job caring for our fur babies! It was clear by her advance questions that she is conscientious and experienced in pet care. We appreciate her careful attention to instructions and her proactive communication.â
About: Iâve grown up with dogs, cats, horses, you name it. Animals are underrated as members of the family in my opinion and I just want to make sure any animal in my care is treated like family. I take care of my animals (two dogs and a kitty cat) daily and they have a pretty set routine, I would be working my schedule around their routine and working on my days off. Iâm happy to drop in and check on your babies and give them love and attention on long work days. I know how stressful it is to be at work knowing your baby is alone at home and Iâm happy to help!
About: I have many years of caring for pets and ran my own kennel in Florida for about 13 years and was a Vet technician for 8years Iâm available weekends and can also be on call if needed. I can also be available on some Wednesdayâs and holidays Iâm open to any times I will care for your pet as if they are my own fur baby and will provide what is needed to take the best care of your pet
The median cost per visit for pet sitting in Winchester is $20
Pet parents share their Rover experiences - Winchester
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 teamâhere to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Roverâs secured platformâno cash or checks required.
Reservation protection
It doesnât happen often, but if your sitter has to cancel, weâll work with you to find a new sitter.
World-class support
Weâre friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your pets like family
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
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Popular requests near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 5 repeat pet sitting clients
FAQs for Drop-In Visits - Winchester
Frequently asked questions about Rover
The average cost for Pet Sitting in Winchester on Rover is $27.75 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .
As of July 2026, there are 98 sitters on Rover offering Pet Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your petâs routine stay on track, or keep you updated on your petâs mood and energy levels.
Whether youâre at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winchester stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitterâs needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
If you would like updates while youâre away, you can discuss with your sitter how many or how frequent youâd 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, donât 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 Justiceâs 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 Roverâs 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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