Pet Sitting Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
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.
“Susan did a great job taking care of our 100 lb Maremma. She was on time for all the sessions, and spent plenty of time with our dog. Our dog really liked seeing her. We will definitely be using her again.”
“Wonderful pet sitter! I couldn’t have asked for better care for my senior kitty. Ami was patient, loving, and attentive to all of luna’s special needs. I felt completely at ease knowing she was in such caring hands. She kept me updated and treated her as if he were her own. I came home to a happy, content kitty, which meant the world to me. I highly recommend her to anyone looking for someone trustworthy, compassionate, and especially wonderful with senior pets! ❤️🐾”
“Amanda was amazing with our two cats! She dropped in to check on them, feed them, clean the box, and give one of our cats medicine. She always stayed to play with them and she went above and beyond to clean up after them. They loved having her around!”
“Kiersten was very prompt. Spent the agreed amount of time with our dog. Everything was done according to directions. Our dog, who can be skittish with some people, enjoyed her visit.”
“Elias took fantastic care of my tricky kitty, including administering meds in food and dealing with frozen wet food (Smalls) which is trickier than scooping dry food or opening a can. They were very responsive communication-wise and enthusiastic. I will definitely turn to them again for kitty care when I next leave town.”
“Ayden was a fantastic house sitter. He took incredible care of our numerous animals, and even noticed that our pellet stove had malfunctioned and let us know! We highly recommend him.”
“Jorden was amazing with our large lad for this drop in! This was our first time leaving Whiskey for an extended time and I think Jorden was the perfect person to check in on him. Will definitely be rebooking in the future!”
“Nadine was Fantastic, it took a few visits for our Cats to warm up to her, she kept the kids Litter box’s clean, and food bowls Filled, also Vacuum around their Litter Boxes, so their area was always Clean, the Bangel Brothers love her time spent playing with them! We are Extremely happy with Nadine, and will Definitely use her Services again when we travel out of town!”
“We’ve had Amber drop in on a few separate occasions now and have had a great experience each time. She’s been attentive to both dogs behaviors and makes sure to check in with questions or concerns. I have a peace of mind when Amber visits if I’ll be away from home for an extended time during the day. Based on the photos, the dogs definitely have a great time with her too!”
“Emily was amazing with Pepper, my shy hound. Emily showed up promptly for each visit and was very thorough. Even her pre-visit questions were thorough. She is very caring and kept me very informed. I highly recommend Emily.”
“Kendra was fantastic with doing a whole weekend of drop ins for our pup, she gave great updates and tons of pictures! So happy with her, and we would definitely have her help us again!”
About: Hi there! My name is Taylor. I absolutely love dogs and believe that most times they are better than people. I will take care of your dog(s) as if they are my own. I am available all day every day except between the hours of 3-6 pm. I love running and playing with dogs and do not mind cleaning up messes. I have two dogs of my own, a black lab and a hound mix that I absolutely adore. I love taking them for hikes and just spending as much time with them as I can. If you choose me to help take care of your dog(s), I promise you will not regret it. Thank you for taking the time to look at my profile! I work as a school teacher right now so am only available after 5 during the week and anytime during the weekends. After June 17th, I will be on summer vacation and will be available all day every day. I have a fenced in yard and a black lab that loves other dogs to play with if you'd like for me to bring them to my home to get some energy out.
“We had a great experience with Lori for midday drop-ins during a busy work week! My dog is older, was recovering from surgery, and isn’t always great with strangers — so I wasn’t sure how it would go. But he warmed right up and had great fun on their visits! Lori is responsive, responsible, and great with my dog. I loved the photos of him so happy to see his new pal each day. Will definitely book again! Thanks Lori!”
“Maggie is a natural with animals. She’s calm and confident around them and people too. Our Merry can be shy but she was fine with Maggie right away. Maggie is polite, presents herself well, and always on time, with a good attitude! We will use her again.”
About: I’m a very responsible and loving pet owner. Have rescued many pets and now have found myself with some free time and would love to help new pets and people! With notice, I am completely free on Wednesdays, Thursdays, Saturdays & Sundays. (Monday, Tuesday & Friday I can be available for a few hours in the am) I have a fenced in yard with plenty of space to play and a kiddie pool to cool off in! I have three very friendly doggos myself but plenty of space so they can be kept separate if you desire.
About: Ive been caring for pets for many years. I had a dog walking business over a decade ago. We taken care of our own and others elderly dogs. We like taking dogs on long off leash walks in groups if possible. Dogs are always welcome to cuddle up on the furniture. Im a stay at home-mom, homeschooling. We go to play groups and trips but we can plan our day around dog walks. We take the dogs out first thing in the morning on leash as our yard isnt fenced. We are happy to come feed kitties and water plants. We love taking dogs out on walks and caring for them in our home. We love going on long walks mid day out in nature
The median cost per visit for pet sitting in Winchester is $25
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.
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
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 6 repeat pet sitting clients
FAQs for Drop-In Visits - Winchester
Frequently asked questions about Rover
As of August 2026, there are 448 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 pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re 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 sitter’s 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 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:
- 86% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 94% 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 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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