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.
About: Through my life I have experienced taking care of family pets, from the puppy stage to crossing the rainbow bridge. I often think I love animals more than people. I am currently working from home part time with flexible hours, so I can play with and cuddle your fur babies as much as they want. I can board, pet sit or just walk your dog weekdays or weekends day or night. I have a fenced in yard with one senior dog. I can crate a dog up to 40lbs. We can go for walks if desired.
“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!!”
“Lawton took such amazing care of my fur babies and my home while I was away on business. She was a wonderful communicator throughout, sending pictures, videos, and daily report cards that gave me peace of mind and reassurance that everyone was happy and well cared for. This was my first time using Rover, and Lawton made it such a great experience. I will definitely be a repeat customer and would highly recommend her to anyone looking for a caring, responsible, and trustworthy pet sitter!”
About: I’m an experienced dog owner with years of hands-on care for dogs of different breeds, sizes, energy levels, and personalities. I currently care for a cat (My sweet Sassy) and multiple dogs, including German Shepherds, Belgian Malinois and my small breed Corgi Beagle mix Luke-y so I’m very comfortable with large, active, and high-energy breeds. I’m experienced with structured walks, exercise, feeding routines, basic commands, medication schedules, and giving each dog individualized attention. I understand that every pet has their own personality and routine, and I will treat your babies with the same patience, attentiveness, and love that I give my loves. I’m currently in the military but love nothing more than hanging out with my babies - and more babies we meet the greater! :) My babies are such a huge part of my everyday routine, so adding another pup to the mix comes pretty naturally to me. We’re big on walks, outside time, playing fetch and tug and just hanging out on the couch. I’m used to planning my day around my cat and dogs and making sure each gets the attention and exercise they need. I have multiple dogs of my own, so I know every dog is different and has their own personality and needs. I’m very comfortable with XL / big dogs and high-energy breeds, but I’m also big on keeping everyone safe and structured. I’ll follow whatever routine you have for your pup and treat them like I would want someone to treat mine.
“Danny & Jennifer were amazing! I can not recommend them enough. From the daily updates, to our specific accommodations, to the care and love they showed our cats, I truly couldn’t be more grateful for these two! Leaving our cats in the hands of someone else is very stressful, but Danny and Jennifer made it so easy for us to not worry as we knew they were in the best hands possible!”
“It was our 1st time having a person to check in on our cat Maggie and it just went so well! Brooklyn took good care of her as if she were her own. She spent time playing with her and showing her kindness. Maggie soaked it up and returned the love by rolling on the floor wanting her tummy patted. We will definitely be requesting Brooklyn in our future trips away. Thank you much Brooklyn!!”
“Cleo did a fantastic job with twice a day drop in visits for our pup. She was attentive, prompt, communicative, and just overall incredible! Our dog requires twice a day oral medication and she can get finicky with taking it. Cleo was able to get her to take it every time. She also was very perceptive with noticing changes in our dogs eating and bathroom habits which she promptly brought to our attention. We couldn’t be happier with her service and recommend her wholeheartedly for anyone in need of help with their dogs. Will definitely be reaching out to her again next time we need to be out of town and can’t bring our pup with us!”
“Barbara was great! Our Lulo is a nervous doggie and Barbara was very patient and made sure Lulo went to the bathroom during her visit. The report we got after the visit was very informative and had some pictures too. Thanks a lot and we'll call you next time we need someone checking on Lulo.”
“Patricia has been a lifesaver for our family. With a change in our working schedule (one spouse no longer working remotely) and traveling, we needed a person to let our dog out mid-day. She is responsive to our needs and our dog enjoys his breaks with her.”
“Cammie was super sweet to my little dogs which made me feel better leaving them at home!! I felt totally comfortable with her in the house! Would highly recommend her!”
About: I have been doing pet sitting since high school and have been a volunteer dog walker for the Humane Society of Missouri for 11 years. I currently have one customer not through Rover and have had more in the past, but I am looking forward to my first Rover job! I love animals (cats, dogs, and other animals). I don't have any pets but hang out with my brother's dog a lot when he is out of town. I walk dogs at the Humane Society on Tuesday but am free most hours and days since I have reduced my time delivering with Doordash. I am looking to build up pet sitting time and can schedule my days around this most days. I can visit your home and spend time with your pet. I can walk your pet, give them food, water, and medicine as needed, and let them outside to go to the bathroom. Your dog will feel comfortable on his or her walk or your pet will enjoy the drop-in visit and time spent with me. I can leave your pet in a certain part of your house or crate at your request.
“Paige followed instructions exactly as laid out, was on time, and the dogs clearly loved her. She is so friendly and such a warm presence, dogs warmed up to her immediately. Very lucky to have run across her!”
“Thank you for AGAIN taking great care of our big guy Skye. He obviously enjoys his visits and I appreciate the detailed communication. My sons always ask if we have new pictures from Skye’s visits while we are away. And they said “he loves Alicia.” Thanks. 🩶”
About: I’m a lifelong cat lover with 12+ years of hands-on experience caring for my own cat, who recently passed away after a wonderful life. While I’m not ready to adopt yet, I’d love to care for yours. I’ve fostered a shelter cat, cared for a friend’s cat for about a year during COVID, and have cat-sat for friends many times. I also have some experience with dogs through friends—walking them together, spending time at dog parks, and playing with them at home. I’m comfortable around dogs of different sizes and personalities. I work from home full-time, which gives me a flexible schedule and allows me to provide attentive care throughout the day. Depending on your pet’s needs, I can easily incorporate pet care into my daily routine and ensure your cat receives consistent attention, companionship, and care. I live in a house with a calm, cat-friendly environment and understand that every cat has its own personality, routine, and comfort level. Whether your cat enjoys playtime and attention or prefers a quiet, predictable space, I'll make sure they feel safe, comfortable, and well cared for during their stay.
“Liana was fantastic. One of my kitties is sick and I really only needed a drop in to help me administer his medication. Not only was she caring, but she was very patient and did not make me feel rushed or add additional stress. I would absolutely put full confidence in her, should I need someone trustworthy to watch my fur babies in the future. Thank you again Liana!”
“Kate did a wonderful job taking care of our two kitties. She was easy to communicate with, arrived on time and followed the instructions that I provided. I have marked her as one of my favorites in Rover.”
Pet parents share their Rover experiences - Winchester
Cindy is absolutely wonderful with our pups. We have two elderly girls who require a bit extra, including diapers and limited mobility, and Cindy has no problem with these added complexities. She is a great communicator too! It makes us so much more comfortable knowing our dogs are well taken care of when we are out of town. I highly recommend Cindy!
Lawton took such amazing care of my fur babies and my home while I was away on business. She was a wonderful communicator throughout, sending pictures, videos, and daily report cards that gave me peace of mind and reassurance that everyone was happy and well cared for. This was my first time using Rover, and Lawton made it such a great experience. I will definitely be a repeat customer and would highly recommend her to anyone looking for a caring, responsible, and trustworthy pet sitter!
Cleo was fantastic with Lumi! She was reliable, communicative and sent us great updates and plenty of photos after every visit. She made sure Lumi got her walks and potty breaks, had fresh water and food, and spent extra time playing with her and giving her some attention and cuddles. It gave us a lot of peace of mind being away knowing Lumi was comfortable and well cared for. Cleo clearly took the time to actually engage with her rather than just stopping by to check the boxes. We would absolutely book with her again. Highly recommend!
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.
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.FAQs for Pet Sitting - Winchester
Frequently asked questions about Rover
Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.
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 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 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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