House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.

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Top rated Winchester house sitters
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Eve is so lovely! Such a nice human and really cared about our bulldog babies, which is all we could ask for while being out of town. She was very attentive towards them, gave them cuddles/attention and stuck to their strict schedule, which has kept them very happy pups. Thank you so much, Eve, and look forward to having you watch them again in the near future!”

About: I started caring professionally for animals when I was just 16 years old. In the veterinary facilities over the years, I worked my way up from kennel attendant, to customer service representative, to customer service supervisor, to customer service manager, to reproduction veterinary assistant. Over these years I have cared for dogs and cats of all ages. During my time as a reproduction veterinary assistant, I found a passion for breeding/deliveries/neonatal puppy care etc. I took this passion and started caring for other people’s pregnant momma dogs within my home. I delivered the puppies, and raised them for infinite weeks until said breeders found their forever families. I raised, cared for, and trained over 150 puppies within my home during the last 4 years. I established long lasting relationships with not only the momma dogs families, but also the families of many of the puppies I was blessed to raise here. Many of which now come to me to watch and care for their dogs/puppies while on vacation, busy day at work, or maybe need a bath/blowdry/brushout/nail trim etc. when needed. I wanted to open up my home and extend my love and animal care for anyone else who may need my service. I am home all day most days. Now that my kids are grown and come and go on their own, I have ability to care for others pets and fully accommodate any needs they may have. When pets are in my home, they can roam freely within designated areas, sleep in beds with us like they are family, or be crated off and on if preferred by their families. We have a fenced yard for outside playtime and a designated turf area for dogs to do their business.
“This was our first time using an in-home dog sitter after losing our previous dog unexpectedly at a boarding facility, so we were understandably very hesitant. From the moment we met Vickie, she immediately put us at ease and gave us the confidence to leave our new pup at home while we were away. Vickie went above and beyond by visiting a few times before our trip to help our pup feel comfortable with her in our home. While we were gone, she kept us updated with daily photos, which meant so much to us, and she even took the time to water our garden. We came home to a happy, healthy pup and a house in perfect condition. We’re so grateful for the care and attention Vickie provided and would absolutely love to work with her again. I highly recommend her to anyone looking for a trustworthy and compassionate pet sitter.”

“This is the second time we have used Richard to sit with Duke. Duke can be very anxious when left with someone other than my wife and myself but with patients Richard was able to get him to calm down and finally relax. We highly recommend Richard and we plan to use him again.”

“Skylar was awesome! We traveled from out of town and last minute decided we needed a dog sitter for a couple days in our hotel room. She was very accommodating. Her response time was always immediate and she sent updates as well as photos of our boy while she was with him. If we come back to California we absolutely will use Skylar again!”

“Alivia was great with my dog TJ! Her communication was excellent and she sent pictures and video. They had a great time. This gave me such great peace of mind. She cared for my TJ like he was her own fur baby.”

“I hired Kaylee to sit at my home with my Belgian Malinois with separation anxiety. I appreciate her quick responses thru the Rover App, and her willingness to arrive for an early morning appointment. We will definitely call Kaylee again in the near future.”

“Kristen truly did an amazing job! She sent lots of pictures to me while I was on my trip and kept me very updated. I fully trust her and would definitely have her again! She stayed at my home and took care of my cat and my German shepherd! They loved her!”

“Caleb & Sara stayed over & cared for my little pack of pups, and cat couple with devotion. Kept me posted, sent pictures and made my time away, worry free❣️💕💕 Will ask for them again in a heartbeat!!”


About: I am extremely reliable, I treat animals with a one of a kind type of affection. I pay good attention to their needs and wants. I don’t have a weekday job, when I do work it’s for a brief 3-5 hours on weekends or online work. I am able to give the pet any extra attention needed. My home is extremely safe. We live in a nice neighborhood with a close by park. My family adores animals. We have a clean living area.
About: I have been a devoted pet caregiver and self owner since the age of 10. I have experience training and care giving for many different type of breeds such as huskies , poodles , jack Russell’s, German shepherds, pit bulls , and more. I always have experience with cats as well and love them just as much. My passion for the genuine care of animals is immense and I would strive to give the best service always. I have been fortunate enough to take some time away from my 9-5 and have had a dire need to pick up a hobby of something I genuinely would LOVE to do. My schedule is completely open to the needs of fur babies! I have one extremely friendly and loving husky who would love to engage with other pets just as much as I would. I have a large fenced backyard for play and gates that block off any potential hazards such as a open road.
“I recently had the pleasure of using Maria as an all-day dog sitter, and I couldn't be happier with the experience. She was very friendly and immediately put my mind at ease. Throughout the day, she provided plenty of updates, sharing photos and messages that showed how much fun my dog was having. It was clear that she genuinely cares about animals. I felt completely trusting leaving my pup in her care. I highly recommend Maria to anyone in need of a reliable sitter!”

“Kairo treats Jasper with love and care! I get the cutest pics and updates from him throughout the day and he is always on time, responsible and leaving my house spotless. Thank you again Kairo!”

“Melinda is a true gem! She helped me out last minute and was so courteous and respectful of my fur kids. She went above and beyond to make sure I felt they were taken care of. Would I use her again? I have used this service a lot and she is the one who will stand out as the best that i have ever had. So friendly, so willing to help, super respectful, and just a cool person to boot. I would highly recommend her to anyone.”

“Anthony did a wonderful job caring for our two one-year-old puppies. He was very communicative and kept us updated with great photos, which gave us peace of mind while we were away. He has a fantastic personality—friendly, reliable, and professional. We’d be happy to book with him again!”


About: Hi there! I recently moved here from a farm town in Oregon, where I grew up surrounded by animals of all shapes and sizes. Having lived on a farm with everything from horses and cows to emus and chickens, I developed a deep comfort level and respect for animals early on. I’ve personally owned six dogs and three cats, so I understand the unique personalities and needs of different breeds. Beyond my own pets, I’ve been the go-to sitter for friends, coworkers, and managers for years. Whether your pet is a high energy pup or a shy cat, I pride myself on providing a calm, reliable, and loving environment. I can’t wait to meet your furry family members! I am currently transitioning between roles, which means my schedule is wide open! Pet care is my primary focus right now, allowing me to provide full-time companionship, frequent walks, and a consistent routine for your fur baby. Whether they need a midday potty break or extra cuddles throughout the day, I’m available to give them my undivided attention. When I’m in my client’s home I love to focus on 'active supervision.' This means we aren't just sitting around; we’re engaging in enrichment, going for walks, and ensuring they get the mental stimulation they need. I am also very comfortable administering medications or following complex dietary instructions, ensuring your pet’s health is the top priority. I also don’t mind doing little things around the house, whether that be bringing in mail or watering plants, happy to help! (:
“I cannot explain the peace of mind having her at my house with my panicky dog during fireworks gave me. My dogs absolutely loved her. I could not be happier, she deserves every single one of these 5 stars.”

About: Hi! I have a 2 year old 60-lb Boxer dog and I also had 3 Shih Tzus for 16 years so I am used to large and small dogs, energetic pups and senior dogs. I’ve taken classes with trainers that trained with Cesar Milan focused on dog psychology and calm confidence. I can care for senior dogs and administer eye/ear drops, medication, and gentle handling. I can also care for playful or large dogs and help get their energy out. I am available for short or long walks, short or long overnight stays, house sitting, bathing, and drop ins. I have a flexible schedule and reliable transportation. I’m available for requests to care for your pets and am excited to meet your fur babies! I am very aware of my surroundings and doors/gates to ensure dogs to not escape or run off. I have a high energy 2 year old boxer that I have crate trained and am used to taking all necessary precautions to make sure pets are safe and secure.
Over 23 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
There aren't enough good words in the world to describe Diane! We have a difficult dog that also needed medication and special attention. She not only stayed here and kept her company, but she did the following without even being asked: •Trained our dog •Walked her multiple times per day •Played with her constantly •Sent constant photos, videos, texts and updates •Kept a written schedule of her medication •Put a shelf and all of the contents back after our dog knocked it down •She even cleaned the house before we got home! She is honestly worth twice the rate she charges. I will never use another pet sitter in the area. She made our vacation so much more enjoyable because we knew our dog was in amazing hands.

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Winchester is $60
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 house 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.
Sitters in Winchester average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winchester on Rover as of Jun 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 2,265 house sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 16 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winchester.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winchester house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.



