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 156 pet parents in Winchester have booked pet sitting
Winchester, Find top rated pet sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: Of all animals I have the most experience with dogs. I love dogs all shapes and sizes We've always had a dog at home and I have lots of experience, caring for playing with and walking dogs, including bath time. I'm a recent graduate of heritage high school. I took agriculture at school and worked with the animals on our school farm I'm looking to do rover as often as possible. I don't have any other obligations at this time. So I can dedicate myself to your pets. I am very careful about fences and doors. I'm mindful of owner instructions regarding where their pets can be. And where they are not allowed. I am mindful of them while they are eaten. And while they are playing, to make sure that they remain safe. I checked the pavement before I take a dog out on walks to make sure it's not too hot and always make sure to wash their bowls so that I can help prevent bacteria
“Dawn was so wonderful with our baby Luna! She provided very detailed updates and photos each day we were away. She was very gentle and patient with our little kitty. Luna is a shy cat, but Dawn had the expert cat sense to allow her the space she needed to grow her trust. Dawn really put our mind at ease.”
“Ashleigh was so great with our 3 giant “puppies.” I loved having the daily reports and feedback. She caught the cutest photos of them too :) Highly recommend her services! Our doggos loved her. We will definitely request for her again.”
About: I know what it’s like to be an anxious mom to a furbaby and wonder if your pet sitter will show up the way you need them to. I have had four dogs since the age of 12 and love them more than anything else! I also had 3 cats when I was younger :) I will do everything in my power to show your babies love and give them top rated care! I currently have open availability and pet sitting is my sole job. I am able to care for senior pets and provide pills as well. :) reach out with any questions! I just moved here from Chicago and right now I’m just babysitting so I haven’t a lot of flexibility and time to care for your baby! I do not offer services at my home at this time but look forward to working with your pets and providing them with the highest level of care and adhering to all routines
About: What sets me apart is the trust I've built with my clients. Many are repeat clients who feel comfortable leaving their pets in my care, even for vacations lasting over a month long. I'm reliable, highly responsive, and believe communication is key. I'll keep you updated with photos and messages while following your pet's routine to help them feel safe, comfortable, and loved. From tiny cats to large dogs, I treat every animal as if they were my own and every home with the utmost respect, so you can enjoy your time away with complete peace of mind. I have a flexible schedule, which allows me to provide pets with plenty of attention, exercise, and companionship throughout the day rather than just quick check-ins. Whether it's walks, playtime, feeding, or simply keeping them company, I enjoy making sure each pet feels comfortable and cared for. As a pet owner myself, I understand the importance of consistency and sticking to your pet's normal routine. I always strive to make them feel safe, happy, and loved while you're away. I believe pets are happiest when they can stick to their normal routine. During overnight stays, I provide full care including feeding, fresh water, walks, potty breaks, playtime, cuddles, and any medications or special instructions if needed.
About: I’ve been helping my friends and family take care of their pets for years while taking care of my own elderly dog. I’ve helped with feeding, bathing, and medication for the animals and provide the upmost care for them. I’m currently available every day of the week at certain times due to college. Times im available are; Mon 10:30AM-10PM, Tues 5PM-10PM, Weds 10:30AM-1:30PM and 7PM-10PM, Thurs 3:30PM-10PM, Fri 6AM-10PM, Sat 6AM-10PM, Sun 6AM-10PM. I’d love to take care of any new furry friends and talk to you more about how it can fit into my schedule if you’d like to book! I’m very gentle with animals, if they’re afraid to approach me or be around me I’ll keep my distance to keep them calm as possible. I’ll set their food and water and wait for them to eat in their own time since I already have the habit of doing so with my own dog due to him being very picky about what he eats. I always keep a close eye on them.
About: Animals have been a part of my life for as long as I can remember! I grew up surrounded by cats and dogs, and over the years, I've gained hands-on experience caring for animals of all ages, breeds, sizes, and personalities. My experience goes beyond everyday pet care. I've attended obedience training classes with several of my own dogs and worked closely with a professional dog trainer to better understand canine behavior, body language, and the individual needs of each animal. This has helped me develop a patient, attentive approach to caring for dogs with different personalities, including those who may need extra time, reassurance, or structure to feel comfortable. I've cared for puppies, senior dogs, and pets with special medical needs. My experience includes administering oral medications, assisting with post-surgery recovery, caring for rescue puppies, and helping dogs work through separation anxiety. I also have experience providing overnight care for cats, including feeding, playtime, litter box maintenance, and helping a rescued kitten adjust to a new home. At home, I'm a proud pet parent to Nala, my 11-year-old Greyhound/Shepherd mix, and Koda, my 5-month-old Chiweenie! We also share our home with my roommates' two senior dogs, giving me daily experience caring for dogs of different ages, breeds, sizes, and personalities. Living in a multi-dog household has taught me the importance of recognizing each dog's individual needs, understanding their body language, and maintaining a safe, comfortable environment where every dog feels loved and secure. I'm a firm believer that every pet deserves more than just the basics. Whether it's reinforcing their favorite tricks, enjoying a walk, engaging in playtime, or providing extra affection, I make an effort to connect with each animal and understand what makes them happy. I also know how important routine and consistency are to a pet's well-being. When caring for someone else's furry family member, one of my first priorities is learning their established schedule, habits, and preferences so I can provide a familiar, comfortable experience while their owner is away. I will treat your pets with the same love, patience, and attention I give my own! I'm an early bird, usually starting my day around 5 a.m., and I currently work part-time three days a week with a fairly flexible schedule. This allows me to make time for pet care throughout the week and accommodate a variety of schedules. Caring for my own dogs is already an important part of my daily routine, so incorporating walks and drop-in visits for your furry family members is something I genuinely look forward to! I understand that pets thrive on consistency, and I'll do my best to accommodate their established feeding, walking, and bathroom schedules. Whether your pet needs an early morning potty break, a midday walk, or some extra attention and companionship while you're away, I'm happy to discuss a schedule that works for you and your pet's needs. Your pet's safety, comfort, and happiness are my top priorities! I understand that every animal has their own personality, routine, and individual needs, and I take the time to get to know them so I can provide care that feels familiar and reassuring. Before caring for your pet, I'll make sure I understand their feeding and bathroom schedules, medical needs, behavioral tendencies, and any household rules or special instructions. I believe maintaining consistency is especially important when their favorite humans are away, and I'll do my best to keep their daily routine as normal as possible. For pets who may be shy or anxious, I take a calm, patient, and confident approach. I never want an animal to feel pressured into interacting with me. Instead, I give them the space to observe, explore, and approach me when they're comfortable, allowing trust to develop naturally. I'm also comfortable following detailed care instructions, including administering medications when needed. During walks and drop-in visits, I'll remain attentive to your pet's behavior, comfort, and surroundings to help ensure they have a safe and positive experience. And one of my favorite parts of pet sitting? Sending photo updates! I love capturing those little moments that let you see what your furry family member is up to while you're away. You can expect regular updates and photos so you can enjoy your time away knowing your pet is in caring hands.
About: Hello, my name is Belinda. I have been a fur mom for 10 years and I truly love spending time with dogs. I’m able to give your dog all the attention needed, and they would never be unattended. Feel free to bring their favourite toys or let them choose from our selection.I have a large gated backyard that your dog will enjoy. All dogs will get plenty outdoor time. My days start early, so drop off and pickup times are pretty flexible. I’m not currently working, so my full time job would be caring for your pet! Flexible schedule and I offer extended stays as well. Only sitting at home I’ve got experience with it all! I’ve also administered medication to dogs of all ages and sizes. lover of all pets, young and old, big and small. ( I DONT ACCEPT PITBULLS). And for allergy reasons I don’t accept CATS We can do walks, hikes, swimming, even to a play day at the park. I Live on the west Side in a house with a fenced yard and friendly neighbours!
About: With pet care experience, I stand out by offering training for puppies and providing PTSD Therapy for both pets and owners. My dedication and unique skills ensure a secure, nurturing, and healing environment for your beloved complains. Pet care seamlessly integrates into my daily routine. I work nights at Walgreens Distribution Center Sunday to Thursday nights and go to school Tuesday and Thursday Mornings. I’m available from 8 am to 7 pm Sunday, Monday, Wednesday, Friday and Saturday. Message ahead for Tuesday and Thursday availability. During dog walks, I prioritize your pet’s well-being, carrying a water bottle with an attached bowl, eco-friendly poops, end of walk treat, safe and dog-friendly trails, and parks.
“Ana Claudia took great care of my cats. There was plenty of food available for them when I arrived home and the litter boxes were all clean. Best of all, she spent time playing with them and giving them love. She sent pictures of them having a good time.”
“We went overseas for ten days and knew Karina would reliably care for our 2 dogs, 2 indoor cats plus feral cats that visit. Drop in visits twice a day walking dogs & feeding plus keeping eye on home gave us peace of mind. So thankful for Karina❣️”
About: Animals have always been a huge part of my life, and I have over 2 years of hands-on pet-sitting experience caring for dogs, cats, and reptiles. I am comfortable with pets of all sizes, including large breeds, puppies, and senior animals that may require extra patience or special care. My experience includes overnight stays of up to two weeks, daily walks, feeding, bathing, grooming, administering medication, and providing plenty of love and attention. Pet owners often describe me as patient, trustworthy, communicative, and attentive to their pets’ needs. With my own reliable transportation and a genuine passion for animal care, I strive to make every pet feel safe, comfortable, and loved while their family is away. I have cared for approximately 10 pets and treat every animal as if they were my own. Pet care fits naturally into my weekly routine. I work Monday through Thursday from 8:00 AM to 6:00 PM, but I am fully available on Fridays, Saturdays, and Sundays for pet sitting, walks, drop-in visits, and overnight care. I am committed to giving pets the attention, exercise, and companionship they need while their owners are away. I have reliable transportation and always make sure pets are cared for safely, consistently, and with plenty of love. While I am unable to offer boarding in my own home, I take great pride in caring for pets in their familiar environment. When staying in a client’s home, I treat both the home and pets with the same respect and care I would want for my own. I always follow household rules, feeding schedules, walking routines, and any training or discipline methods already in place so your pet experiences consistency while you’re away. I am clean, responsible, and non-disruptive, and I make it a priority to leave your home just as I found it. I am happy to clean up after myself, wash dishes, take out the trash, bring in mail, and help keep things tidy during my stay. My goal is to provide a safe, stress-free experience for both pets and owners, giving you peace of mind knowing your pets are loved and your home is being cared for responsibly.
“Breeanna is amazing! She takes excellent care of my cats and is very communicative. We are able to have worry free trips because we know we can trust Breeanna to take care of our fur babies. Thank you so much!”
“Kristen was amazing and kept all communication with us during our vacation through Rover app! we have not had anyone watch our fur babies in a very long time so we were very scared to take a mini-vacay as we were in fear they would not get the love we give by someone else! She superseded our expectations.She will be our "go to fur baby sitter" for all our future travels! Thank- you for the trust and reassurance you provided our family! we highly recommend her to anyone in need of a fur baby sitter!”
About: My passion is to care for animals, I’ve had many people rely on me to care for and to watch their dogs. I love to care for them. Im here at home 24/7 so I will always be home to care for your dog or cat. I have a doggy door to provide potty break all day I have a fenced in yard your puppy can easily run around if they wanted. If you need your fur baby to be crated I can definitely do that for you too.
About: So many dog walkers and sitters, how do you choose? I have been a dog trainer and handler for over 11 years. I am certified pet first aid and CPR. Through my hard work and attention to detail I've earned the trust of working with canine support teams, trainer Shawn Baxendale out of Los Angeles and two prominent rescues Wylder's and Lucky Puppy. I have your dogs well being at heart. I am highly responsible and reliable in caring for your family pet. If you like we can schedule a meet and greet so that you can get a feel for who I am and also see that your pet would be staying in a safe and clean environment. My purpose is safety, comfort and fun I work from home so I am available to play with your pups and provide any care that is needed for your beloved family pets. I have a fenced in yard with nice green grass and two pups to help me keep your doggies company. I have toys and balls to engage your pet so they get some exercise and if allowed I take them for walks. My main objective is always safety but I also make sure your pup feels comfortable and loved. I give your pet a home away from home experience. This is not a loud and crowded facility where your dogs will sit by the gate in anticipation of your return and or have to wait for a place to rest or some attention. I also do have crates available if needed.
About: Where do I begin? I’ve had dogs since the time I came out of the womb, but I officially received my own baby at the age of 6. Our family loves dogs, as there has never been a time we had less then 2-3 dogs in our house. Right now I have 3 dogs and I love them more then anything. They are inside dogs and I wouldn’t have it any other way! All of my dogs have always slept with me in bed, but it could be due to me being the one who feeds them lol. My passion is to love and care for all dogs! Being a vet use to be my passion, but I could not bare to see a pet go! I love dogs more then anything and any chance I get to pet one that passes by, I will take! I hope to have the chance to meet as many dogs as I can through this site as I will love on them as if they were my own.
The median cost per visit for pet sitting in Winchester is $25
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 team–here to help if you ever need someone to talk to.
Why Choose Rover?
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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.
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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
The average cost of Pet Sitting in Winchester on Rover is $28 per visit as of October 2026. Most bookings cost between $11 and $42 per visit. 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 October 2026, there are 3,502 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 .
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 , 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
- 91% 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 .
sitters on Rover set their own , 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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