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. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I have always been around and loved animals.. I started pet sitting when I was in a single mom and working in the schools. I would care for dogs and house sit when coworkers went on vacation. Then I did some child care and pet sitting for weekends when coworkers went out town for emergencies. I have had many beloved pets growing up; cats, dogs, guinea pigs, rabbits, fish, and hamsters. Currently, I have a 2 dogs, cat and pet pig that is house trained. Caring for my animals bring so much joy and happiness especially watching them play with each other like children. I promise you I will care for your pets just like they were my own. I will provide you with photos for reaccurance and updates while under my care. I can"t wait to meet you and your pets :)
“We couldn't be more grateful for Jessie! She took amazing care of our beloved shepherds and our home while we were on vacation. Before finding Jessie, my husband and I rarely traveled together—we're very particular about who we trust with our dogs and our home. Jessie exceeded our expectations in every way. From the moment we booked with her, communication was clear, timely, and thoughtful. She kept us updated throughout our trip with messages and photos that gave us total peace of mind. It was clear our pups were happy, relaxed, and in great hands. We were able to truly enjoy our vacation knowing everything back home was being cared for so well. Jessie’s attention to detail, reliability, and genuine love for animals completely won us over. We feel incredibly lucky to have found her and are already looking forward to future travel plans now that we have someone we trust completely. Highly, highly recommend!”

About: I've been taking care of animals since I was 5 when I got my first dog, and I've been caring for animals ever since! I've cared for many different species, such as dogs, cats, birds, rabbits, cows, fish, and a couple of reptiles! I'm always looking for new animal friends and would love to meet yours! I'm currently a full time college student, and have two classes a day. I will be available for pet care at all hours other than 10-11am, and 12-1pm during my classes. I have a nice big hallway for your pet if a kennel is needed, and I have great access to a nice, safe walking path, plus a big yard for pets to play. I am very adaptable and can make anything work!
About: Since I could walk, I’ve had animals in my life. I’ve helped care for animals of all kinds ranging from fish, cats and dogs to chickens and horses! Feel free to reach out with any questions or concerns. I am currently off work and have open availability to take care of your furry friend(s)! If you have any questions, feel free to reach out and I will get back to you ASAP! Currently, I have 3 cats, a Chihuahua and a 30 gallon fish tank. As far as my cats go, I feed them canned food and have dry food out regularly. They have yearly vet visits and I keep them up-to-date on boosters. My cats are enriched with cuddles, playtime and scratchers in multiple places throughout my place. They love to be brushed often as well. My dog, Butterball, has his nails filed as often as needed and he loves cuddles under the blanket while watching tv. He goes outside on a lead multiple times a day. My fish tank is cleaned and maintained biweekly. I also always have spring water on hand to keep water levels appropriate.

About: My family has always owned a dog. Ever since I was young, my family and friends have relied on me to care for their animals, whether it be a walk, or an overnight sit. I’m a current Ball State Social Work grad student and love paying visits to the local Animal Shelter in my free time! I am a part time grad student at Ball State University, and also work part time at a daycare. I still have a lot of free time I’d like to fill throughout the week doing something I love, like taking care of animals. I am very attentive when it comes to caring for other peoples babies. Safety for myself and the pet is my number one priority. I do have a fenced in big back yard, and I also live right next to campus!
“Maura was a wonderful house/animal sitter. She gave us updates with pictures throughout our weeklong vacation & left our home in pristine condition. It’s always hard to leave your “babies” behind but having Maura there really gave us a sense of relief. We would highly recommend her and have already booked with her again!”

About: I grew up with 3 large breed dogs and have done 2 years of dog walking / pet sitting! During my 2 years of pet sitting, I took care of puppies from 6 weeks old to senior dogs. Things that fell under the description of ‘took care of’ are; picking up poop, feeding / following dietary schedules, administering medications, walks, play time, bathroom breaks, training work, mental stimulation (snuffle mats, kongs, etc.) I do daily dog walks, and am helping my parents raise and train a German shepherd! I also have 2 cats of my own at home. I will travel to your home by car! I do not offer care for your pets in my home due to my cats not being very sociable haha!!
About: I have always love all kinds of animals since I was little. Im hoping to get my some soon when I get my own place. A lot of people always told me that I'm an animal whisper because a lot of animals really trust me more than others. Owners have told me how amazing it is to see their fur babies trust me and let them pet them when they normally don't let anyone pet them. I am currently looking for a part time job right now. As I am a Caregiver working through the weekdays. I am sure we can talk more about the days and times that work for both of us! I can’t wait to meet your amazing animal! I have a fenced yard, and two cats that will make sure your animals have companionship! In this house we spoil our animals and your animals equally with lots of treats, cuddles, and playtime!
About: I have pet sit for many years. I love meeting new animals. I enjoy pet sitting because as a social worker I am able to come home to an animal and sent time with them. Animals are the way I cope. I have plenty of time to play with animals in the evenings and weekends. My schedule is very open for this and I am excited to have this opportunity I will ensure to keep everything the way I found it or even better. I know animals do best in their own environment so I have no problem being in other peoples homes. I show respect.
“Kaitlin did a wonderful job with our dog. I was nervous as this is the first time we’ve used her and she exceeded our expectations! She helped work on his behavior issues and kept me updated on how he was doing. I will be definitely using her anytime we go out of town!”

“I give Ben an A++. I couldn’t have asked for a better new buddy and caregiver for my fur babies. Ben’s calm and welcoming presence is exactly what my dog needed while I was away. I feel so much better knowing they are just as cared for and loved as when I am home.”

About: I Have experience with cats of most sizes dogs, birds, arachnids an even reptiles. I will treat your furry one like they were my own. Partner is working an i am full time dad looking for side income that doesn’t require me to leave our little one. Our child loves animals as well. I live in a pet friendly apartment complex with tons of sq. Footage for your furry one to get plenty of exercise. It is only me my child an partner who reside in our apartment.

About: I have always cared for my friends animals when they are traveling and I also have had my cat Nola for 5 years. I’m also familiar with animals having anxiety and how to care for them by creating a routine that’s safe and fun. I have an open schedule currently so I’m open to flexibility during the day and some afternoons. I’m on break from my Masters program so my time is pretty open. I would make sure that any special needs your sweet baby needs is taken care of with extreme amount of love and care. I understand how important it is to be gentle especially when meeting new pets who might have anxiety.
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!
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.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available 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.

