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 83 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: Animals have been part of my life for as long as I can remember. I grew up surrounded by dogs, cats, birds, fish, turtles, hamsters, gerbils, and even chickens, and each one taught me something different about patience, joy, and unconditional love. Over the years, I’ve rescued dogs, helped others find their forever homes, and volunteered at shelters and adoption events. I have a soft spot for senior pets and pups with special needs. My dog Dumba is turning 16 this February, and supporting her through her golden years has taught me how to be gentle, attentive, and adaptable. Before Dumba, my dog Cookies bravely fought cancer for many months, and I cared for him through two surgeries and ongoing treatment. Because of experiences like these, I’m comfortable administering medication, monitoring health changes, and giving extra support to pets who need a little more care. I also love working with cats! Since rescuing Zoro when he was only 8 weeks old, I have developed experience with basic grooming, brushing, and keeping litter areas clean and comfortable. Your pets are family, and I’ll care for them with the same love, patience, and attention I give my own. My schedule is flexible, and I’m happy to accommodate your pet’s routine. I'm currently offering daily walks and drop‑in services. I live in Winchester and know the area well, so your dog can enjoy peaceful walks around Horn Pond or fun playtime at Sheepfold Dog Park. I share my home with my senior dog, Dumba, and my goofy cat, Zoro. They’re both used to being around other animals, but my space isn’t large enough to comfortably or safely host additional pets. Because of that, I offer care exclusively in your home, where your pet feels most secure and where their routine stays consistent. When I’m caring for your pet, I follow your house rules and make sure your pet’s environment stays familiar and stress free. My goal is to respect your home, maintain your pet’s routine, and give them attentive, loving care while you’re away.
“Angela was wonderful and attentive with our two cats. She’s highly communicative and took great care of our cats, and our home, during twice daily drop in visits. We came back to two happy boys. I absolutely recommend Angela!”
About: I absolutely love dogs! I’ve had large dogs all my life, have pet-sat for many friends and neighbors, and have fostered 15+ rescue dogs for Last Hope K9 Rescue. I am also a dog training enthusiast, and have been training my Australian Shepherd for obedience and agility for the past 6 years. I recently interned with a local veterinarian, handling all sorts of pets including dogs, cats, and rabbits. I live right near the Middlesex Fells Reservation, and love bringing canine friends along on Fells adventures! I am home all day all summer, with lots of time on my hands to play with pups, take them on hikes, and give them all the attention they deserve! I am 18, and I live with my parents and sister (16). I have a fully fenced yard. It is accessible to the neighbors' two friendly dogs who often come over to play, but the yard can be closed off as necessary. I have a 6 year old Australian Shepherd who loves other dogs, but he usually keeps to himself when they stay over.
“Angie did a fantastic job of taking care of my old kitty. She was very responsive and we really appreciate her alerting us to a potential issue for a pet that wasn’t her responsibility!”
“James is the best!!! Very communicative, provides full run through of activities and behaviors during the visit. He is very loving to the dogs and takes lots of photos and videos! Will 100% book again.”
“Caroline was great with my dog, who can take a little to warm up to people. Now he loves her and we are so grateful for her checking on him with her busy schedule.”
“Sanela was great and I would definitely use her in the future to care for my 2 cats. She is caring and treated the cats as her own. She took lots of pictures and was easy to communicate with. My car Leo requires insulin injections every 12 hours and I was so happy to find someone that could provide that level of care.”
“Thank you, Jolene, for checking in on my two cats over a holiday weekend with a last minute booking! Jolene’s communication and timing was excellent. While checking on the cats, she filled their bowls, gave them treats, and brushed them. I appreciated her time and attention!”
“Shawn dropped in to take care of our two cats multiple days during our long vacation. It was a huge relief knowing they were in good hands and getting photos each day. She followed our detailed feeding instructions that involved wet food with medication mixed in, and measuring out dry food on a scale. She also gave us detailed updates on their behavior and it was clear she really cared about their comfort and mood while we were gone. Thank you Shawn, would definitely book again!”
“Noila took amazing care of my two kitties for two full weeks! She sent daily pictures and videos of them playing, and included any other information about her check ins with them. She made leaving town so much less stressful! Fantastic experience.”
About: Used to work in a pet shelter as a volunteer for 2 years whilst in school. I am pretty relaxed with various breeds and sizes I work part time currently and looking for a side hustle that works around my schedule as a college looking to make extra money money I am a very patient pet owner considering I have have fostered kittens that are extremely energetic has conditioned me to be careful and cautious
“Elisangela is super nice and did a wonderful job caring for my cats. Even my very shy/scared cat came out to see her! I highly recommend her for any animal care you need.”
About: I adopted my first dog in second grade. He was my responsibility and as I got older, I learned that I loved going for walks outside as much as my dog. Now that I'm older, I love taking friends' dogs for hikes in new locations. I have even managed to train one of my friend's reactive dog so she pulls on the leash less. I also briefly fostered animals when I was in graduate school. I am a teacher on summer break, so I have plenty of hours to devote to your pet and look forward to enjoying plenty of summer outside time with your dog. I have walked a wide range of dogs, including a couple of reactive pit bull mixes. I have experienced triggering situations with dogs and know how to either handle them or avoid them.
“Lindsey has been great with our puppy! I love the check ins and pictures from each drop in. Lindsey can actually get her to walk in the leash and she is such a happy pup during the day!”
“Kerri is extremely flexible and wonderful with our pup. She is patient and kind. Our pup is the happiest to see her! She is definitely our go-to person to entrust our pup’s care !”
The median cost per visit for pet sitting in Winchester is $25
Pet parents share their Rover experiences - Winchester
Matilde was an outstanding sitter for my two cats. She gave detailed updates and shared many photos. My cats instantly warmed up to her, when they can sometimes be shy. She is definitely a natural animal person. I will definitely re-book and highly recommend her services.
Cheryl always goes above and beyond to make sure our kitties are happy when we’re away. Would 100% recommend. She really has a way with animals and cares deeply about their wellbeing and even their quirks. Thank you again! I’m glad you and Scooter are friends!
On time, very communicative. Our silver lab doesn’t trust many people and can be very standoffish. During the meet and greet he went up to Monica, sniffed, wagged his tail and felt comfortable with her. Our chocolate lab immediately brought her a toy-so he built trust with her. Will def use Monica again!
Blane did a phenomenal job taking care of my cat, Auggie! The level of detail and care that Blane put into Auggie’s Rover cards was awesome—lots of photos, details about what they did together, and info about Auggie’s behavior. Blane was always responsive, showed attention to detail, and got along so well with Auggie despite this sit being their first time meeting each other. I booked Blane as a last minute, fill-in sitter, but I will definitely be rebooking. Highly recommend!
We all love Shawn! She's been caring for our puppy 4x/week for the last month. She's consistent, thoughtful, and he's so happy to see her each morning. Communication has been super easy and she's very attentive to the daily, ever-changing needs of a new puppy. Thanks Shawn!
This was my third time booking Anneke for drop-in visits to take care of my two cats while I'm out of town. She is fantastic! She is very reliable and clearly cares about the happiness of my pets. She always checks in to make sure my travel home isn't delayed so the cats don't go too long without food. I feel very confident leaving my fur babies at home knowing Anneke will visit them.
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
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
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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 Drop-In Visits - Winchester
Frequently asked questions about Rover
The average cost for Pet Sitting in Winchester on Rover is $32.1 per visit (as of July 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 July 2026, there are 10,791 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:
- 90% of sitters can help with special care needs
- 95% 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 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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