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 130 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.
“Kristin was wonderful with our little Lucy. We are so excited to have found a trustworthy sitter in town. I could tell from our meet and greet that Kristin was a genuine animal lover who really enjoys what she does. Kristin sent us the cutest photos with a detailed update. Excellent communication before, during and after the visit. Everything was locked up tight as we had hoped. We will not hesitate to use her services again and have peace of mind. Thank you so much!”
“I loved seeing the pictures of her kids loving on my cat! Normally my cat is a stage-five clinger, which makes me extra nervous when leaving for trips. Knowing that she was in the hands of such a sweet family made my vacation that much better!”
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!
“Dina was fantastic! She gave me the peace of mind that I needed to enjoy my trip. I looked forward to each update, and I knew that my cats were in good hands with her.”
About: I’m an experienced pet and dog lover who has been actively involved in animal rescue for 25 years. I’ve worked with dogs and cats of every type and temperament—from high-energy pups and shy rescues to senior pets and those with special needs. I currently share my home with two dogs of my own and remain very active with local animal rescue efforts. I work from home, so I’m available for boarding, daytime care, last-minute requests, and nearby potty-break drop-ins in the community. Your pets will receive plenty of enrichment throughout the day, lots of outdoor time, and a calm, consistent routine. They’ll have access to comfortable furniture, socialization opportunities (when appropriate), and engaging activities so they feel secure and stimulated while in my care. I typically accept dogs up to 40 lbs and can make exceptions for larger, well-trained dogs. I’m happy to care for multiple dogs at once when schedules and temperaments allow. As a lifelong animal lover, I genuinely enjoy the time I spend with pets and am committed to giving them the same attention, patience, and care I would want for my own. I look forward to meeting your furry family members and providing a safe, enriching experience they (and you) can trust. I work from home, so I’m available for boarding, daytime care, last-minute requests, and nearby potty-break drop-ins in the community any day of the week. As a work-from-home pet sitter, I offer flexible availability for overnight boarding, daytime care, last-minute bookings, and local potty-break drop-ins. Your pet will enjoy a calm, consistent routine filled with plenty of outdoor time and daily enrichment. I provide a secure and stimulating environment complete with cozy furniture, interactive activities, and opportunities for safe socialization when appropriate.
About: Ive taken care of dogs and cats all my life I personally have 2 dogs and one cat. Ive lived around animals my whole life and love them all dearly. I am currently a college student and I am in a musical theatre production but I will have plenty of time for your pets in between classes and before and after rehearsals! I will give your pets all the attention I do not offer services in my home because my cat is very jumpy but I will gladly come over and keep your baby company, walk them and feed them.
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: 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!
About: Hi, my name is John and I have loved and cared for dogs and cats since I was 15. I've had several rescue dogs since 2011, including a tri-paw Belgian Melanois, who passed away in 2019. I currently live with Max, a beagle rescue. I mostly work from home so will be with your dog all day. I'll take your dog and my dog Max on a minimum of four walks during the day in downtown Lexington. I'll provide attention and care for your dog. There are are plenty of green space during our walks. Safety, wellness, and happiness for any dog under my care is priority. I would like to schedule a meet and greet to gather as much information as possible about your dog and to see how your dog does with Max.
About: I’ve grown up on a farm, caring for various types of animals including dogs, cats, horses, hamsters, guinea pigs, and fish. I have years of experience working at animal shelters and clinics which makes me prepared for any type of situation. I’m skilled in providing loving, reliable care for all animals, big and small. I’m currently a full time college student so I will have classes throughout the day but am available in the mornings and the afternoons. Weekends are usually free unless noted otherwise. Ensuring a safe, calm, and comfortable environment is my priority. I’ll make sure your pup feels secure and happy while under my care, providing them with all the attention and safety they deserve!
About: I've lived in a cat household for 17 years and have loved every second of it! I also have experience doing drop-ins, walks, and overnights with dogs ranging from the puppy stage to senior dogs. I love the snuggles and play time, and would love to help take care of your fur babies whenever needed! I work from home and am flexible and very dependable when needed! I live in south-central Lexington and am 10-15 minutes away from just about everywhere in town. I understand how important it is to ensure the happiness of your fur babies. I will engage your dog or cat in fun playtime that lets them get their energy out, take them on walks (if applicable), and then top it all off with a good meal and plenty of belly rubs to make any furry friend happy!
About: I've been an animal lover my entire life and truly enjoy caring for pets of all ages, sizes, and personalities. Whether it's dogs, cats, or other furry family members, I treat every pet as if they were my own with plenty of attention, affection, playtime, and care. I'm dependable, detail-oriented, and understand how important it is to keep pets comfortable and maintain their normal routines while their owners are away. I also genuinely enjoy house sitting and take pride in keeping a home clean and well cared for! My goal is to give you peace of mind knowing your pets are happy, safe, and loved while you're gone. I am currently finishing my current job and will be available to take on pet care bookings full-time until I start school in September. Once school begins, I’ll still be available before and after my classes (9–4:30 weekdays) as well as on weekends. I’m flexible and committed to providing dependable, loving care and making sure your pet feels safe, happy, and well cared for while you’re away. I am committed to providing the best care for your pets and your home. I will follow all routines and instructions you provide to ensure your pet feels safe, comfortable, and cared for while you’re away. By the end of your trip, I hope to be your pet’s new best friend!
“This was our first booking with Jordan and it was great! She was prompt, professional, and kind. Our dog is slow to warm up to new people but Jordan was able to easily spend time with him and take him on a long walk with no problems. I highly recommend Jordan. In fact, we have two more services booked with her already!”
“Glenn and Terril did a wonderful job taking care of my little buddy Ike Jr. Especially given late notice on Thanksgiving week. Updates and pics daily. Just a great experience overall!”
About: I adore animals, and with me, your pet will always remain safe and pampered. I have a long history of animal care, having grown up raising and caring for just about anything you could imagine. I am a college student and athlete, and I am an expert at juggling my workload. I can be wherever needed at any point, except when I have class or soccer games. I believe in treating everything with proper respect and care, especially when that entails others' property. I have no issue cleaning messes made by pets, and will always do my best to prevent any misshaps.
About: I've had at least four dogs as long as I can remember. As a child, they were my first companions and my second caretakers. Even as I grew into an adult, they were always there to comfort me and to brighten the darkest of days. Dogs hold a very special place in my heart and I am eager to give back what they so willingly give; love, acceptance, understanding, comfort, and joy. In the last two years, I have gone from four dogs to one, due to Cancer and Congestive Heart Failure, and I must admit that their absence has affected me deeply. I miss them so so so much!! I'm one of those people that celebrated their dog's birthdays and bought them copious presents for Christmas. While my friends were pulling out their family pics, I was always pulling out my dog pics. I share this same sentiment towards birds, rabbits, and cats; all of which I had growing up. Being surrounded by animals as a child was a great experience. It even prompted me to volunteer at the ASPCA for almost a year. As I hope you can tell, I will not only provide what your pet needs to survive, but I will also provide him/her with special attention and love. I look forward to meeting with both you and your pet! Until then, take care! I will be able to fulfill any house/pet sitting duties without any issues, as I am able to balance my obligations responsibly and with respect to myself and those that hire me. While pet/house sitting, I will abide the rules given to me. This could include when they play, where they sleep, any medications needed, when to eat, etc.
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.
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 $22 per visit as of October 2026. Most bookings cost between $14 and $28 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 763 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:
- 90% of sitters can help with special care needs
- 96% 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 .
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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