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 5 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
âKimberly is kind and generous with her time! She made the Rover experience comfortable. I was excited that our fur baby would have someone genuinely interested in her wellbeing and clear on the expectations. I will definitely reach out again!â

âBreeanna 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!â

About: A military veteran with veterinary technician experience, I understand how important it is to find someone you can trust with your pets. I offer loving, personalized care in a comfortable home environment with a fenced yard, plenty of attention, and a family atmosphere. I welcome dogs of all ages, including playful puppies and senior pets who need extra patience and care. Your pets wonât just be watched; theyâll be treated like part of my family Caring for animals is something I genuinely love, and it naturally fits into my everyday family life. Days are filled with playtime, walks, cuddles, fresh water, meals, and plenty of attention. I love getting to know each petâs unique personality and making sure they feel safe, comfortable, and loved. I happily make room in our routine for your furry family members because, while theyâre with me, theyâre part of our family too. My goal is for you to feel at ease knowing your pets are getting all the love and care they deserve while youâre away A veteran, I bring a strong sense of responsibility, structure, and attention to detail to everything I do, especially when caring for your pets. In my home, I provide a loving, safe, and comfortable environment where pets are treated like part of the family. I have a fully fenced backyard where they can enjoy fresh air and playtime, and they are always supervised to ensure their safety. I take pride in following your petâs routine, paying attention to the little details, and making sure they receive plenty of love, exercise, and attention. Whether caring for pets in my home or yours, my goal is to give you peace of mind knowing your furry family members are in caring, responsible hands.

About: My sister and I had pets since I was a child. Frogs, fish, turtles, dogs/puppies, bunnies, and a parrot. I would say I am well rounded in pet care. I can watch your furbaby in home if you like. If you need someone to drop in and take care of your pet while out, I am also willing to do that. I know how to administer oral medications if that is of need. I currently have one rabbit and a lab. Making your pet comfortable and happy is what I strive for. I am currently working from home so I have more than enough time to take care of your animal. I will be available to feed , and do any extra activities that your animal may need. * I do home stays but I will not stay overnight I can stay all day and leave super late but I can not stay overnight. When in your home if you have schedule that you like me to follow I can do that. I like to just have fun play,give cuddles, and for some dogs like like to be lap dogs I can do that too.
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. Iâm 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 petâs well-being, carrying a water bottle with an attached bowl, eco-friendly poops, end of walk treat, safe and dog-friendly trails, and parks.
About: Hello, my name is Belinda. I have been a fur mom for 10 years and I truly love spending time with dogs. Iâm 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. Iâm 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 Iâve got experience with it all! Iâve 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 donât 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: 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: Iâve been helping my friends and family take care of their pets for years while taking care of my own elderly dog. Iâve helped with feeding, bathing, and medication for the animals and provide the upmost care for them. Iâm 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. Iâd love to take care of any new furry friends and talk to you more about how it can fit into my schedule if youâd like to book! Iâm very gentle with animals, if theyâre afraid to approach me or be around me Iâll keep my distance to keep them calm as possible. Iâll 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.

âAlicia is quick to respond and very reliable. We booked her services for a last minute trip. She took good care of our pups and worked with us on our changing schedule. We will definitely have her help us out with any future needs.â

About: Iâve been caring for dogs for most of my life. Years ago, when I lived in Long Beach, CA, I worked with Tidy Dogs fostering pups until they found their forever homes. I also volunteered at places like Best Friends Animal Sanctuary in Kanab, Utah, spending as much time as I could helping dogs in need. Those experiences showed me just how much joy it brings me to be surrounded by dogs and to make a difference in their lives. The idea to start boarding dogs came years later, after I had a bad experience boarding my own pups in Las Vegas. That inspired me to create a place where dogs could feel safe, cared for, and truly at home while their families are away. My home is clean, dog-friendly, and secure. I use plenty of Sunbrella patio cushions because theyâre easy to clean, donât collect fur, and the dogs love them! I also cook for my two dogs â a Frenchie and a Jack Russell â who love to help welcome and train our four-legged guests. When your dogs stay with me, I want them to feel like theyâre on vacation too. Together, we go on fun adventures â bike rides, walks, games of fetch, swimming, and even cozy movie nights. Browse through my photos to see some of the wonderful dogs who have blessed my life with their companionship. If you have any questions, please donât hesitate to reach out. Iâd love to meet you and your pups! I'm a early riser so walks in the morning and my spouse does evening walks. My retired mom lives with me and we are a 3 person team. We all care for the dogs. I have a fenced yard and can crate if needed. I'd rather they be free but if crate train is a request I can do that. Brushes, walks and playtime. Clean house and waters routinely changed. New dishes every time dog is fed.
About: I've taken care of all kinds of animals! I have grown up around dogs and have had a dog for most of my life. I am also a behavior analyst, so I have a little bit of background in terms of reinforcement systems :) I work fully remote from home, so I am home everyday. This makes it super easy to care for whatever you may need for that day. Recently said goodbye to my senior dog that I had for 13 years, so now it is just one 6 year old pup. She is spayed and loves to play, A LOT. We have a fenced yard and a lovely neighborhood for walks. She is an inside dog, so yours would be too. I have an extra medium sized crate for use as well. She is a lil princess of the house, we are very dog-centric here! We also have a 1 year old, so if your dog doesn't do great with kids or you're unsure, we are probably not the sitter for you.

âThis was my first time using Rover and I'm so glad I found Katrina! She took great care of my elderly kitty who requires medication and sent me pictures and updates after each visit to let me know how he was doing. It was very comforting knowing that he was well taken care of while we were away! I will definitely use Katrina again.â
About: I have experience working with puppies and many breeds. I will reinforce desirable behaviors through positive reinforcement. I have experience giving medication. I can take your pet to the vet for you. I have many years of experience working with animals at a veterinary hospital and animal shelter/rescue. I am available short or long term. I am available week days and weekends. Caring for pets is my vocation. I donât have any schedule restrictions I have outdoor and indoor space according to your petâs preferences. While outdoors, your pet will be supervised in an enclosed yard. I provide opportunity for water loving dogs to play in the pet pool. I provide ânose workâ for those dogs that need mental activities.
âJon and Steph are the sweetest people and we felt more than comfortable having them drop in our home and care for our pup. We received amazing feedback and updates after drop ins and we will continue to use them in the future. We are so happy with our experience and so is our dog.â
About: I will be available during the holidays. Please let me know your dates and needs and I will be happy to work something out. Had dogs all my life and cared for them in all sorts of situations; medications and therapy walks. Monitored them after surgery and held them down for medications they hated. Walked them, ran with them, biked with them and laid down with them. I enjoy animals and I want to spend as much time as I can with them. I will CARE for your pets. They will have fun while I am there. When I had my dog I had a fenced yard with a doggie door for access to the house. I sat with him during thunderstorms and took care of him after ACL surgery. We played ball three times a week or more. He endured my short lived biking phase. He loved the convertible and hated the sedan. I think of him every day.

âAndrea is the nicest and most responsible pet sitter we have ever had. She honestly loves the animals she takes care of. I will definitely be using her in the future. Sheâs a great human!â

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 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.
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 is $32 per visit as of November 2026. Most bookings cost between $27 and $44 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your petâs 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 November 2026, there are 3,489 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 petâs routine and the sitterâs 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 petâs 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 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 with handling special pet needs in Winchester. On Rover:
- 87% 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 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 sitterâs 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, youâll 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.



