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.
“Cats are very happy and well taken care of again! Our most shy baby even came out this time to say hello and that really surprised us and warmed our hearts. Will be using Amy again in the future:)”
About: I’ve always taken care of pets whether they were mine, or someone who needed a sitter for the weekend! Pets are our babies as well! I’m currently between jobs, and have more than enough time in my life right now, and would love to take care of your fur babies! We have 5 acres for them to play on! I have two of my own dogs, who are little social butterflies. They would gladly take on some new friends!
About: I am a SAHM and have plenty of time to care for your pups! I absolutely love dogs— they are a huge part of our family. I know how hard it can be to find a dog sitter you trust and who genuinely tries to understand each pup’s quirks. I love getting to know them and treat them as my own (which means lots of cuddles and love). Please let me know if you have specific requests! We have a fenced in yard and plenty of comfy places for them to sleep. And because I’m “that” dog mom, I have a FURBO camera, so I can check in on them anytime I leave the house. It even dispenses treats! I am also comfortable with providing end of life care and can take them to vet visits if required. I typically feed dogs twice a day, but please let me know if you have a different schedule for your pups! I’m happy to accommodate. I have a fenced yard and 2 sweet dogs that will keep yours company. They will have access to filtered water and be given organic treats daily! They will all have their separate eating spaces.
About: I am very gentle with all the doggies I care for. I show each one of them love and respect their boundaries. I love to go for walks with them and pick up after any messes they make. I happily clean their dishes and make sure they are well provided for. I’ve only had 1 dog in my lifetime that lived to 12 years old but I have had many dogs around me growing up. I love taking pics and vids of goofy things they do so I am happy to update as well throughout my time caring for them. I am currently working part time so I have a lot of flexibility when it comes to animal care. I am happy to make early morning and late night stops to accommodate for their care. I follow the rules you set! I am happy to walk, train, crate, exercise, and play with your animal in ways you prefer and know they like! At home, I only have cats so I feed twice daily (with vitamins and supplements), scoop the litter daily, and do kitty dishes daily as well. We play at night and they have full access (and kitty proofed) to my garage to play in. I am happy to accommodate their lifestyle and needs.
About: What really sets me apart is the level of care and attention I give to every pet I look after. I treat each animal like my own making sure they feel safe, loved, and comfortable while their owners are away. I’m reliable, patient, and I take the time to learn each pet’s personality and routine so they get consistent care.I also have experience with puppy training helping with crate training, potty training, and basic commands as well as senior pet care, including administering medications, assisting with mobility, and providing extra comfort and attention. Whether it’s a playful puppy or an older dog who needs a gentle hand, I can adjust my care to meet their needs. Pet care fits easily into my routine since I work part-time. I have plenty of flexibility during the day and evenings to give pets the time and attention they need. Whether it’s walks, playtime, or cuddles, I make sure each pet gets consistent care and companionship throughout the week. When caring for pets in my client’s home, I do my best to keep their normal routine feeding, walks, playtime, and any special instructions so they feel comfortable and safe in their own space. I make sure they get plenty of attention, exercise, and affection while keeping their environment clean and stress free.If I’m caring for pets in my home, they’re treated just like part of the family. I provide a safe, cozy space with lots of love, play, and supervision. I always make sure they get the care, comfort, and consistency they deserve.
About: I've taken care of all kinds of dogs since I was 13. I personally have 5 current pets right now. This includes 1 dog 3 cats and even a turtle. I got a degree to be a veterinarian assistant and worked in an animal clinic for almost a year. Right now I am a kennel attendant at a doggy daycare. Where required online training was required. We get a variety of different dogs. Ranging from small to large, young to old, even a few dogs with some medicine issues. I'm currently working part-time. In my free time, I take my son out for walks, so I can possibly bring dogs with me. I do have my own car for transportation. I live in a neighborhood where there is a lot of strays, so when I walk my dog, I carry a spray shield, which is citronella and animal deterrent from Pet Safe. Working at a dog daycare, we get a lot of dogs with some type of medical condition. From clean Bulldogs folds to make sure dogs take their medicine when needed.
About: I've adopted senior dogs and one cat. I can do long walks on the trail and dog park visits! I love animals and take care of all pets as if they were my own. I work remote and have a flexible schedule. Available for drop ins or stays with your pet. I'm free most weekends and can take the pets out as frequently as every hour if needed. I have a fenced yard for pets boarding with me. Meet and greet required in advance to ensure they our pets get along. My cat is dog friendly.
About: My history with dogs began the day I was born. My family has always had at least one dog, and I've always had responsibilities regarding dogs. My dog, Oscar, is a rescue and recently turned one. He loves people, other dogs and all other animals he’s met so far. I began house sitting when I was 17, and have been taking care of pets and homes for 15 years.
The median cost per visit for pet sitting in Winchester is $20
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 5 repeat pet sitting clients
FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
As of November 2026, there are 661 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:
- 88% of sitters can help with special care needs
- 95% 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 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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