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 126 pet parents in Winchester have booked pet sitting
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.
“I could not have been more blessed than I was finding Kristin! I never once had to worry about my babies while I was away! She spent quality time with them and took care of all their needs! She went above and beyond in my opinion! Will definitely be using her again! Thank you for everything!”
“Laura was great, I had her let out one of my fur kids and she was flexible when I needed to push something a little and sent pictures so got to see the kiddo some during the day. She also did the simple but important little things like making sure he had water which I appreciated.”
“I could tell how much Isabella loves animals and was completely confident that she would take the very best care of my baby girl. Willow was in good hands and I will definitely book Isabella again.”
About: Hi! My name is Marianes and I truly love animals. I have experience taking care of dogs, including walking, feeding, and giving them attention and love. I am a responsible, patient, and caring person. I understand how important your pet is, and I will treat them like family. I will make sure your dog feels safe, happy, and comfortable at all times. I would love to help you take care of your pet! I am available during weekdays after the morning and I have a flexible schedule. I can adapt to your needs and make sure your pet gets the attention and care they deserve. I always make sure pets are safe and comfortable. I follow all instructions from pet owners, keep doors secure, and pay close attention during walks and visits. Your pet’s safety is my priority.
“Dina is awesome!! She is great with dogs and intuitively knows what they need. She always sends me adorable update photos of her loving on my puppy when I’m away at work!”
About: Families book with me for loving, family-style care, frequent photo updates (if desired), and the peace of mind that comes from working with a sitter trusted by repeat clients since 2021. 🐶 I simply love dogs. They are truly my passion. 🐾 Caring for them isn’t just something I do, it’s something that fills my heart. 💚 I have a special love and deep experience with breeds such as English Bulldogs, French Bulldogs, Lhasa Apsos, Shih Tzus, Shorkies, Greyhounds, Cavalier King Charles Spaniels, and Bernedoodles, but I genuinely enjoy caring for all breeds and personalities. Every pup deserves to feel safe, adored, and understood. Dogs have been a part of my life for as long as I can remember. While I can’t be a full-time fur mama to them all, dog sitting allows me to pour love into as many pups as possible and I wouldn’t trade that for anything. It has been such a blessing to learn and care for new breeds through my bookings. Each dog I welcome into my home deepens my knowledge, strengthens my skills, and grows my love for dogs even more. What truly sets me apart is the family experience I provide. When your dog stays with me, they aren’t just “watched”—they become part of our home. While your family is away, your fur baby enjoys a warm, loving, family-style environment filled with cuddles, attention, and genuine connection. I happily send plenty of photo updates (if desired) so you can relax knowing your pup is safe, happy, and well-loved. My family loves dogs too, and on occasion, trusted family members may stop by simply to meet my furry clients and share a few extra cuddles (not to assist with care), but purely because they enjoy loving on dogs. 🐶 Some of my favorite repeat clients even get to travel with me, including family visits and store outings (photos available!). Your dog gets real-life experiences, companionship, and enrichment—not just a place to stay. Over the years, I have lovingly been a full-time fur mom to up to three dogs at the same time, gaining daily, hands-on experience managing multiple dogs under one roof. Currently, my home includes Khaleesi, my sweet English Bulldog girl. I also carry deep love for my Lhasa Apso, who crossed the rainbow bridge in August 2023 🌈. My Shorkie was lovingly rehomed with an older family member to provide emotional support, and while she no longer lives in my home, she remains part of my extended family story. I’m also what I proudly call a “Mid-Woof” 🐶—I have independently and successfully delivered 4 litters of puppies in my home and have personally whelped, nursed, and raised two litters until 4–8 weeks of age before helping them find their forever homes. I understand canine behavior, comfort, and care on a deeper level than most. I will love on your fur baby as if they were my own. Bulldogs, in particular, require a special level of patience, knowledge, and care and if you’re a bulldog parent, I’m absolutely your girl. (Bulldog hugs are always welcome 😉) I’m proud to share that I have 10+ repeat clients, including several families who have trusted me with their fur babies consistently since 2021—relationships built on love, reliability, and peace of mind. I look forward to being your dog’s Bonus Mom while you’re away. Let’s get your pup booked, loved, and spoiled! 🐾💕 I work in an office Monday–Friday but return home on lunch breaks for potty breaks and check-ins. After working from home for seven years, I’ve adjusted my availability while remaining intentional and reliable. I’m a mom to young children under 10 who are gentle, respectful, and great with dogs 🥰. I’m available for daytime drop-in visits, and on weekends (when in town) I’m fully available for dog sitting in your home, my home, or for additional check-ins. I have plenty of grassy space where I live in a dog friendly neighborhood. I also have a fur baby to keep your dogs company if needed for service in my home. I have a dog area set up in my home. We also travel to dog parks when weather permits, if your dog needs activities, we will go on walks and even to our favorite dog park!
“I recently moved from NY to KY and was in need of someone to help care for my four dogs. I had spoken to many people and wasn’t comfortable with anyone as I had my prior dog walker in Ny for over 10 years. I found Tanika and she and I hit it off right away: she was super accommodating to my ever changing schedule. I was nervous to have my one rescue dog meet anyone because he could be unpredictable. Tanika came armed with treats and was relaxed and so easy going with all the dogs that he took to her first!!!! Tanika had been above and beyond amazing . She helps with my dogs that have medical issues and she is always there when and if I need her. She takes care of my dogs as if they were her own and I’ve never had to worry about them when I’m away. She is an absolute god send and I highly recommend her!”
“Maggie is so wonderful!! She is incredibly communicative and responsive. She sent so pictures, my mom heart was at such ease. Our fur babies absolutely loved her. She spent such quality time with them and is such a quality person. I would definitely use her services again!!”
About: Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching taking care of animals since I was a kid and I just love it I absolutely love taking care of your fur babies! Their schedule is totally accustomed to your needs and wants as their owners if you create a schedule for them, that would be wonderful and allow me to take care of your fur babies as you would yourself I do services in Lexington and Winchester, I’m currently working full-time with my hours ranging from 6 AM to 4 PM 5 days out of the week! Hours may vary depending on work Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching taking care of animals since I was a kid and I just love it! I don’t offer boardings at the moment but I would love to housesit or do drop-in visits for you!
About: I’ve had dogs my whole life! Had chihuahuas growing up and have labs currently so any size dogs is good with me! I will love and care for your dog as I would my own! I’m an Air Force Vet with lots of extra time so I’m mostly always available! I can be available at my own home or your home as well! I have a fenced yard and two friendly dogs if your pup is fine with other dogs! Can also keep them separated if your pup does better alone (:
“Olivia was great. She gave the pups all the lovings while I was away. She sent pics and was great at communicating. The pups loved her. Will definitely use again!”
About: I have 7 years of experience caring for dogs and currently have three mini dachshunds of my own. I also regularly watch dogs for friends and family. I’m comfortable with feeding, walking, playtime, potty breaks, and giving pets plenty of attention and care. I understand that every dog has their own personality and routine, and I’ll treat your dog like one of my own. I work part-time, so my availability varies throughout the week. I’m usually available in the mornings, on certain weekdays, and can be flexible with walks, drop ins, feeding, and playtime depending on my work schedule. I make sure every pet feels safe, comfortable, and cared for. I follow the owner’s instructions closely, keep feeding and potty schedules consistent, provide plenty of attention and playtime, and always make sure pets are in a clean and secure environment.
“Casey was great watching my two cats while I was gone for over a week! Very easy communication and she sent me so many photos which was great for my peace of mind. My cats warmed up to her so quickly and the photos she was sending me cuddling with the boys made me know my cats were well taken care of while I was away. I’d recommend Casey to anyone looking for someone to watch their pet while they are away, thanks Casey!”
About: I’ve loved dogs my whole life and currently have three of my own. Eli (10) and Luna (6) are rescue dogs who have taught me the importance of patience and understanding every dog’s unique personality. Nimbus (2) has been with me since he was a puppy, so I’m experienced with both energetic young dogs and older companions. After nearly 10 years as a USPS mail carrier, I’ve also learned a lot about dog behavior and body language from meeting dogs of all personalities every day. I know how important it is to approach each dog calmly and respectfully. I understand the trust it takes to leave your pet with someone else, and I’ll care for them like they’re part of my own family while keeping you updated along the way. I work full-time as a USPS mail carrier and typically finish my route between 12:00 and 2:00 p.m., giving me plenty of availability most afternoons, evenings, weekends, and many holidays. Rover is a great fit because it allows me to spend even more time with animals while providing dependable, personalized care for pets in my local community. Whether your pet needs a walk, a drop-in visit, or some extra attention while you’re away, I’ll treat them like one of my own. Your pet’s safety, comfort, and routine are my top priorities. I’ll follow your care instructions closely, whether that’s feeding, medications, walks, playtime, or simply providing companionship. I’ll always treat your home with the same respect I’d expect for my own, making sure doors and gates are secure and leaving everything just as I found it. You’ll also receive regular updates and photos so you can have peace of mind while you’re away.
About: I have been caring of a variety fur babies since I was a kid. I have experience with working with both younger and older fur babies. I am currently working full time while coming my masters online in counseling so I do have flexibility with working overnights. If need more availability please contact me. I have a fenced area at my apartment complex for dogs if needed. I have a variety of teats and toys for cats if needed.
About: I’ve taken care of dogs practically my whole life. It’s one of my greatest passions and most of my life I would dogsit for anyone who would let me growing up. I would love to make sure all of the animals are safe and well cared for while their owners are gone. I currently go to school and work part time, but there is most certainly time for me to fit in helping these families with their animals when they need it. I do live in an apartment complex but I have many years of experience with walking dogs of all kinds so I could walk it when needed. As for as toys, a crate or bedding at my apartment, I don’t have much of that, but could get some if needed.
About: After experiencing the tragic loss of my own cats due to a negligent pet sitter, I became deeply committed to providing the highest level of care for all animals. That experience taught me how vital it is to entrust pets to someone who not only understands their needs but treats them like family. I specialize in senior pet care, offering compassionate support for aging pets, including administering medications, managing health conditions, and providing gentle, tailored exercise routines. I also have experience training puppies, helping them develop good behaviors early on and ensuring they have the structure they need to thrive. My focus is always on building trust and creating a safe, loving environment for your pets, so they feel comfortable and secure when you're away. Above all, I aim to offer peace of mind to pet owners, knowing their animals are in caring, responsible hands. Available almost anytime in Lexington and surrounding areas contact in advance is recommended but we can take last-minute calls depending on the situation and what not. Also I work with you budget! I have a park near me and I do take my own dog to the dog park every chance I get via Lyft and plenty of toys for your fur babies!
The median cost per visit for pet sitting in Winchester is $19
Pet parents share their Rover experiences - Winchester
Kayla was incredible! It was my first time leaving my two cat babies, so I was naturally hesitant altogether because I didn’t know how the girls would take it. I got daily photos, which put my mind at ease. I hope to be able to have Kayla as a sitter for the babies for the foreseeable future. Thank you!!!
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
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2. Meet In Person
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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 for Pet Sitting in Winchester on Rover is $22.2 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .
As of September 2026, there are 751 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:
- 100% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 97% 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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