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 experience with dogs and cats. My pets are treated like family. I am a retired nurse and I will do my very best to treat your pet and home with the utmost care. I am retired from nursing but I’m looking for something to keep busy and to help others. I’m available 95% of the time. I am reliable and can be trusted to take care of your fur baby. I will follow your instructions exactly to care for your beloved pet in your home. I will treat your pet and home with respect and care.
“Isabella is a fantastic sitter! She loves the boys and they love her. She’s a great communicator and gives me updates, which I love! She will also go the extra mile when one doesn’t feel so great! So glad we found her!”
“Hannah was so great with Daisy! She followed all of the instructions we left and made sure to bond and make Daisy feel comfortable while my husband and I were gone all week on vacation. She provided us daily updates with pictures and was very communicative, which made it so much easier to be away from Daisy for a whole week. I would definitely recommend Hannah to anyone needing a gentle and attentive dog sitter!”
“Melissa took wonderful care of our dogs over the weekend! She came and stayed with them, and she sent so many cute pictures and videos. She was super communicative, too - we will definitely work with her again!”
“Sara was excellent and was able to accommodate all of Kylo's needs and provided plenty of updates to give us peace of mind that our dog was in great hands. Sara also went above and beyond in taking care of our home and left it just as is was when we left!”
About: Hi there! Thank you for checking out my profile! My name is DeAnna; I’ve always had dogs in my life (ones of all sizes from Terrier to Poodles to Great Pyrenees) , and have some experience with cats. I am a certified Dog Obedience Trainer with exceptional experience in dog behavior, learning theory, breed attributes and animal husbandry. Unlike other sitters and walkers you may see, I am willing to offer advice for dog training and grooming. I’m a fast learner, pay attention to even the smallest details, I am a compassionate person willing to go out of my way to make sure your fur baby is happy. If you ever need someone to watch your dogs/cats or just someone to get them out of the house to play, keep me in mind! I will always make sure that I leave your fur babies healthy and happy :) I am currently self employed and have open availability throughout the week, which makes even more time to focus on caring for your pups and giving them the best care I have a full fenced in yard within a quiet neighborhood. We own two very spoiled and very loved dogs who will treat your pup like a brother or sister. Outside of the home, my main priorities are your pup’s safety and the fun they have under my care.
About: I grew up with a dogs and cats. I love their snuggles! I have joined Rover to give myself a bit of boost. I used to have a dog named Mabellene, she was wonderful, I currently own a cat. I’ve always had a pet, so they are the first thing on my mind when I’m leaving the office ……or waking up in the morning. I only sit in my apartment on special circumstances, my cat has to be okay with the dog. In your home I follow all rules and basic etiquette when in someone else’s space.
About: I have been caring of a variety fur babies since I was a kid. I have experience with working with both younger and older fur babies. I am currently working full time while coming my masters online in counseling so I do have flexibility with working overnights. If need more availability please contact me. I have a fenced area at my apartment complex for dogs if needed. I have a variety of teats and toys for cats if needed.
“This was my first time using Sierra as a dog sitter. I was in a bind after a scheduling misunderstanding with another dog sitter. Sierra came through and saved the day! Sierra always promptly responded to my texts and sent me updates. She took good care of Dewey and left me house clean and tidy. Sierra spent an excellent amount of time at my house. Would highly recommend!”
“Hannah took excellent care of Kylo and my home! Plenty of updates were sent and Kylo looked very comfortable with Hannah. Everything was how I left it and that was greatly appreciated!”
About: I’ve always had a love for all animals it doesn’t matter what animal they are. When I was 13 I was put in foster care and my first home was at a horse farm and I absolutely loved it grooming,feeding, and riding the horses. My chores were to walk the dogs, feed the dogs, bath the dogs, and also groom the dogs. I love and enjoy the company of my furry friends. All animals are welcome to stay with me and get the same love and care that they get at home. I’m also willing to travel however far away you are. I also really like it if I have a list of routines that your animal does so I can keep them on schedule. If you have one.
About: I have been pet sitting for 5 years and my friends, family and neighbors all have trusted me to take care of their pets for years. I have experience in basic obedience training with young dogs. I have trained my 2 dogs and have done some work with other puppies. I have experience with administrating medicine to senior animals. I also have experience with reptiles, I used to be a pet keeper at a pet store and picked up many useful skills during that time. I am currently working part time. Shifts are about 4 to 7 hours long but only 3 days a week. Daily walks are no problem, I can fit that into my daily schedule. I usually like to discuss with the clients that have booked with me about my schedule for that week. I usually do not house pets in my home due to the fact that we have many animals and things can get difficult. In a client's home I usually follow the instructions that I am provided for the pets diet and routine. I love playing and spending time with all my clients animals!
Over 34 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
I cannot say enough good things about Jimmy. From start to finish, he went above and beyond in every possible way. Before even dog sitting, he took the time to meet my dogs and my cat, which immediately made me feel comfortable and confident leaving my pets in his care. While I was away, Jimmy was incredibly communicative and kind. He sent daily photos and updates, which truly put my mind at ease and showed how attentive and loving he was with my pets. It was clear they were happy, comfortable, and well cared for. When I returned home, I was honestly blown away. Not only were my pets perfectly taken care of, but my house was spotless. He cleaned the house, did the dishes, and even made my bed — something I never expected and appreciated more than I can say. Jimmy is trustworthy, thoughtful, and genuinely cares. We will 100% be using him again in the future, and I wouldn’t want anyone else watching my pets besides him. If you’re considering Jimmy as a sitter, don’t hesitate — he is truly one of a kind.
Jimmy took care of our elderly, special-needs dog and 4 chickens during his stay at our home. Our dog developed an eye infection right before we left, requiring additional medication and treatment twice a day on top of her regular medications. I was very concerned about leaving her, but Jimmy handled all the extra tasks, reaching out to make sure he was providing her medications as prescribed. He communicated regularly and sent photos as her condition improved, and I was greatly reassured. We're so grateful to him for taking such good care of her.
Jimmy was great! Stayed at our house while we was gone on vacation for a week. Took very well care of both of our dogs and also took care of our mums and other plants. House was clean and very well taken care of as well. I would highly recommend him. We will be considering again in December when we leave again for a week. Oh and he sent pictures and communicated everyday with us.
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 May 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 May 2026, there are 413 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, 94% 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.
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