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 92 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%.
“Cheryl was very attentive to my cat's needs, and was responsive when communicating through text chat. I appreciated that she gave my cat some wet food, which I didn't originally include in my care instructions. She also sent very cute meme images with my cat cropped on various backgrounds!”
“Can I give ten stars?? I am so happy we had James to look after our kitty while we were on a rare family vacation! The daily updates and the many pictures and videos were wonderful and made us know right from the start that we had the right person. I 100% recommend James for any pet-sitting job. Ray is happy we're back, but I can see he misses James now!! Thank you, James - you are awesome!”
“Sanela was lovely! She became cuddle buddies immediately with our cats. Great with communication. Her check in comments, pictures, and punctuality immediately calmed any anxiety we had about leaving our boys.”
About: I've loved animals for as long as I can remember. Growing up, my family always had pets, including dogs, cats, and rabbits. Caring for them taught me responsibility, patience, and how to understand each pet's unique personality. I know that leaving your pet with someone else can be stressful, so my goal is to make both you and your pet feel comfortable and confident. I treat every pet as if they were part of my own family, providing plenty of love, attention, playtime, and care based on their individual needs and routine. Whether your pet enjoys long walks, interactive play, quiet companionship, or simply sticking to their daily schedule, I'll make sure they feel safe, happy, and well cared for while you're away. Communication is very important to me. I'll send regular photo and video updates, along with messages about how your pet is doing, so you can enjoy your time away with peace of mind. I'm available for last-minute bookings whenever possible. I have experience caring for puppies, senior pets, and multi-pet households. I'm happy to follow your pet's feeding schedule, medication routine, and any special instructions. I am currently working part time and have sufficient extra time to care for your kitten or cats! My availability is before 11 am and after 1pm daily. I have an apartment with a yard to walk around within gated community if needed. Additionally, it is on the ground floor for convenience or easy access.
About: Hi there! My name is Fernando and I’ve been taking care of pets my whole life. Since I was a kid we’ve always had all kinds of pets; dogs, cats, birds, ducks, even an armadillo. I have experience as a dog walker and pet sitter. I was the daily dog walker of a 13-year-old Bull Dog for the past 2 years, and sadly, he passed away a couple of weeks ago. I’m also currently helping some families when they travel. I take care of 3 beautiful and playful Golden Retriever, and I also do drop-visits and walks for another family with a Maltese. I love dogs! Being surrounded by them and playing with them gives me so much happiness and energy! I’m here to help you with anything you need and take care of your lovely friend 🤍 BTW, the picture on my profile is with my 2 little pugs that I had to leave in Mexico with my parents when I moved, and I miss them every day. I’m currently an Au Pair while I’m finishing my college degree, so I have a lot of free time while the kids are at school, to be specific I’m free from 8 am til 3 pm everyday (except when there’s half days of school). And I’m also 100% free on weekends I always make sure the pet is comfortable and safe, with my services of dog walking, pet sitter and drop-in I always follow all the indications that are provided to make sure the pet is safe.
“Natalie was great! She was super friendly and responsive, she took lots of photos, and kept me updated :) It's hard to tell what cats are thinking, but I think they liked her too ;)”
“Sasha is great! She took amazing care of our two kitties while we were away for almost two weeks. Communication was excellent; she sent little updates and pictures every day. Thank you, Sasha!”
About: What sets me apart is the level of care and communication I provide. I know how much trust it takes to leave your pet with someone else because I’ve cared for my own dog for the past 12 years. I follow their routine closely, and provide regular photo and video updates so you always know how they’re doing. Whether your dog loves long walks, playtime, or simply relaxing with company, I’ll make sure they feel safe, loved, and comfortable while you’re away. Pet care fits naturally into my weekly routine. I work a full-time job with a flexible schedule, including a few work-from-home days each week, which allows me to provide reliable care and plenty of attention. Outside of work, I enjoy staying active, so walks, playtime, and spending time with dogs are something I genuinely look forward to. I plan my schedule carefully to make sure every pet receives the care, exercise, and affection they deserve while their owner is away. If I’m caring for your pet in your home, I’ll treat your space with the same respect and care I would my own. I’ll also provide regular photo and video updates, so you can have peace of mind knowing your pet is happy, safe, and well cared for while you’re away.
“This was our first time working with Nina and we look forward to working with her again. She is friendly, kind and attentive and we felt comfortable that she was a good match for us and with our dog and cat. She responsibly followed our guidance on food and meds which was very important as our dog had suffered a recent injury. We requested and received regular updates on how our little guy's were doing, giving us great peace of mind while we were away. She also sent very cute pictures!”
About: My kids and I are big dog lovers and would love to help care for your furry family members! 🐾 We’re excited to offer dog walking services in the area and have experience with both dog and cat sitting. We understand how important it is to know your pets are in caring, loving hands, and we’ll treat your pets like part of our own family! I work part-time remotely, which gives me a flexible schedule and plenty of opportunities to spend time with your pets! I’m available for walks, playtime, or simply keeping your dog company during the day and early evenings. I live in a 3 bedroom condo in Somerville and have a great, quiet neighborhood and live near several parks. There is ample space for your pet to be comfortable and get exercise.
“Samichya and her husband were fantastic caretakers for my two beagles. They were wonderfully communicative throughout the stay, always quick to respond, and I felt completely at ease knowing my dogs were in such good hands. I came home to happy pups and a house left in great shape. Highly recommend their care.”
“Kristen was such a wonderful help during our holiday travel! She updated us every day on our kitten’s progress and made sure she was happy and taken care of. I always felt like our pet was in safe and loving hands with her! She even went above and beyond by checking on little Hero sometimes twice a day! A wonderful experience, would certainly book again.”
About: Reliable and caring dog walker who is passionate about providing safe, fun, and enjoyable walks for every dog. I’m attentive to each dog’s individual needs, making sure they get plenty of exercise, attention, and love while in my care. Your pet’s happiness and safety are always my top priorities! I work full time as an operating room nurse. I am available on the weekends and have most mondays off. Also available for evening walks. I care for every pet as if they are my own. In a client's home I would follow protocols set by owner and accomodate to whatever dog's needs are.
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?
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 6 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 $16 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 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 November 2026, there are 10,642 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 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:
- 84% of sitters can help with special care needs
- 89% can help with giving oral medications or injections
- 93% 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 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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