House Sitting in Winchester
Find a loving dog sitter to watch your dog overnight in 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.
“Went away for a family vacation for a week and Jenna did an absolutely phenomenal job caring for our dog. Sent a lot of pictures and constant updates to give us peace of mind when we were away! Would definitely recommend Jenna!”

“Jessie did a wonderful job watching my house and taking care of my dog. I could tell after being gone 5 days that Cato was in good hands with the routine updates and pictures. Cato was happy to see me when I got home but was also relaxed. I could tell that he and Jessie got along great.”


“Sarah was awesome. She sent pics & a recap of how the day went every day. The dogs were happy & healthy when we got home. Our place was clean & neat. We definitely will book again. I highly recommend her.”

“Leo took great care of our dog and our house. He sent photos to us everyday, and our dog so looked so happy I thought the pup wouldn't want us to return home. Leo was good with communication. It is obvious Leo loves dogs. I would highly recommend him!”


About: I have extensive experience caring for animals, as I’ve had pets in my home since I was a baby. Growing up around pets taught me responsibility at a young age, including feeding, grooming, cleaning, and making sure animals feel safe and comfortable. Over the years, I’ve cared for a variety of pets and have become very attentive to their needs, behaviors, and routines. I understand how important it is to provide not just basic care, but also companionship, patience, and love. My lifelong experience has made me confident in handling different personalities and ensuring pets are well cared for while their owners are away. I am a full time college student and work a part time job as a server. Most of my availability is in the mornings on weekdays and weekends as needed. I am a reliable and caring pet sitter with extensive experience providing private pet care for families. Over time, I’ve built trust with pet owners by consistently showing up on time, following specific care instructions, and treating every pet as if they were my own. I’ve cared for pets with different routines, temperaments, and needs, which has made me adaptable and attentive in any situation. Whether it’s feeding, walking, administering basic care, or simply spending quality time with pets, I always prioritize their comfort, safety, and happiness while their owners are away.
About: **About me** I have always wanted to move to the country and care for animals all my life. My husband (Patrick) and I currently have three rescue dogs and 5 outdoor rescue cats. We also have two horses Valentine and Peanut that love to walk the trails with us. My passion is caring for animals and I have had years of experience raising all breeds and types of pets! We live in a small home built on 31 beautiful acres. We have a fully fenced large back yard and several wooded trails, a beautiful pond in the front yard and lots of room to play! Your pets will love coming here and it will truly be like they are on vacation. I have 4 grand pups that come to the farm regularly and they get very excited to visit. **About my home/services** I will provide a loving and fun environment for all pets that come here to stay! They will be safe and will love every minute of their stay! **About my neighborhood** We live on 31 acres with only 1 neighbor close. We have a fully fenced back yard and a pond to fetching toys if your pet loves to swim. We have wooded trails that we often take walks on and we will have lots of exercise or just hanging out in the back yard.
“Abby is wonderful and I would highly recommend her. We did an initial meet and greet and I immediately felt comfortable with her. We were gone for 11 days and Abby stayed at our home with our 5 pound Yorkie. We choose an in home sitter because our dog has major separation anxiety. Abby sent us daily updates and pictures and our dog was living her best life as usual!! We already have our next stay scheduled with Abby.”

“Carson did a wonderful job house sitting with our German Shepherd for 1 week. She sent pictures and updates. We were quite comfortable leaving our boy, Jax, in her care. I would not hesitate using Carson again in the future.”

“Tori was absolutely incredible. She provided exceptional care for my pup, ensuring he felt loved and well taken care of during my absence. Her attention to detail and genuine affection for animals truly stood out. I could see how happy my pup was in her presence. Without a doubt, I will be reaching out to her for her services again in the future.”

“Adam and Chelsea provided excellent care to my three dogs! They kept my house clean! I can’t give them any more than five stars, but I would give them 10 if I could. Hopefully I can be a repeat customer if the dogs didn’t scare them off too bad. Adam and Chelsea, thank you for making me feel comfortable that my dogs were in wonderful hands! You guys are the best!!!”

“Lilia was amazing with our rescue pup, Berkley! She is super calm and kind - we could tell our Berkley already felt comfortable around her the first time she met her! She sent us many photos throughout the weekend. She was very communicative and professional. We would recommend her to any friend or family member!”


About: I have done drop in visits, farm sitting, dog grooming, equine care, and taken care of many animals. I have at least 10 references. Love all the animals and will treat them with love and respect. I own a mobile dog grooming business so can make my own schedule. I have my farm animals but I have help from family to care for mine when I’m needed elsewhere. I prefer to let the animals be in their own home as they seem less stressed knowing they will be where there family will be coming back to. They have their comfortable spots and smells and doesn’t disrupt their routine but if necessary I could care for them at my home. Would walk smaller dogs on leash outside or have outdoor pens for larger dogs to get to run.
About: I've been lucky enough to take care of homes and pets in lots of different places, like California, Oregon, and even other countries. All that experience has helped me become really good at providing reliable and loving care for both pets and their people. I’m really good at going with the flow and can easily change my schedule to fit what a pet needs. Whether it’s walking the dog early in the morning, playing with them in the afternoon, or feeding them at night, I’m always flexible and ready to adjust. I always do exactly what my clients ask me to do, whether it’s about feeding their pet on time, giving them medicine, or teaching them good behavior. I know how important it is to keep things consistent for pets, so I try to make their routine as comfortable and familiar as possible.
About: I always insure that pets are comfortable! I’ve taken care of old cats and dogs, and I when they are old like that it’s important to meet their needs first, as most of the time they need a lot of guidance and help. I am currently going into online college, so most of my day is free! I often sit down and watch TV or play video games, but I mostly enjoy writing and drawing in my free time I personally like to ask owners how there pets are in the company of others, as well as if any weather bugs them! The comfort of my pets, and owners is always my number 1 priority! I want to make sure that they are comfortable around me, and I never approach any animal until I’ve let them sniff me, it’s important that they trust me to be around them.
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 $40
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 3 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 $40 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 164 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 15 years of experience. House sitters with repeat customers have an average of 3 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.






