House Sitting In Winchester, MO
Find a loving house sitter to watch over your pets and your home.
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Top rated Winchester house sitters
“Kayla is an amazingly awesome sitter, she sent many pics keeping me updated thought out her stay watching our pets. She truly went above and beyond. Highly recommend!”
“Callie did a fantastic job of caring for Maybel and our home while we were out of the country for an extended period of time. She treated our dog and our home as if they were her own. We got daily updates and photos too!”
“Alex and Christina were very sweet. They sent lots of updates and spent a lotttt of time with our separation-anxiety cat while we were away for the week, and she seemed perfectly content when we returned home! We were glad to have them to help us!”
“Faith was amazing! She took such great care of our dogs and her communication was so great! We were able to relax and know our dogs were taken care of while we were gone!”
“Great sitter. Rosemary sent photos and communicated frequently. Most importantly, she seemed to truly enjoy working with Sydney. Our dog can be a little difficult sometimes and we often come back to a dehydrated, depressed pup. She seemed to be in great spirits and that’s a credit to Rosemary. Would definitely recommend!”
“Lauren was so great with our stubborn bull dog. She is excellent with communication and provided regular updates while we were gone which was so helpful. We knew our pup was in great hands with her. We would definitely recommend her!”
“Super sweet dog-sitter! The dogs loved her. And we appreciate her so much! Abby communicated well and set our hearts at ease. We were able to have a wonderful weekend away knowing the dogs were in great care with Abby. Will hire again!”
“Katie house sat for us and loved on our lab, Fran! She is probably one of the best communicators and sent frequent pictures and videos throughout our 6 day vacation. She was also kind, courteous, and trustworthy. We will definitely reach out to Katie for our next vacation when Fran needs care!”
“Audrey (and her friend Devin) were amazing! She was very flexible with arrival and departure times for our Moose, a 3 year old pup, who loved playing with her fur baby, Duke, as well! She was able to stop by our home twice before the dates we needed her for to meet her and her fur baby and they were both very sweet. Audrey updated me while I was away to ensure my dog was okay and also was very great with giving him plenty of love and attention all throughout the day! Moose was very tired the next day so I know she got plenty of play time and exercise in during her stay. We came home to a clean house that was exactly how we left it. Audrey was overall was very accomodating, sweet, trustworthy, and made it very easy for me to feel comfortable leaving my pup. Thank you Audrey and Devin! Moose can't wait to see you again next weekend ?”
“She took great care of my kitties while I was out of town! She sent pictures often and left my house in wonderful condition. I would absolutely trust her again to take care of my fur babies.”
“Amber was absolutely the best!! J never had to wonder how things were going, she kept me updated with pictures and videos the whole time. I think my pets like her more than me at this point- highly recommend and will definitely be having her pet sit for me again!”
“Reilly was great! She sent updates and took great care of our dog! Will definitely book again.”
About: I treat pets like family – Every walk, meal, and cuddle comes with genuine love and care. I offer overnight stays – Giving pets comfort in their own home (or yours) while their humans are away. I am reliable and trustworthy – Always on time, communicative, and consistent—clients can relax knowing their pets are in safe hands. I specialize in dogs and cats – Confident, experienced care for both, from walks to purr therapy. I build bonds – Pets love me! I am not just a sitter—I am their second-best friend. I am detail-oriented – Meds, feeding schedules, routines—I don’t miss a thing. I go the extra mile – Whether it's cleaning up messes, sending photo updates, or squeezing in a few extra belly rubs, I do it all with heart. I currently work from home, which allows me time to spoil your furry friend and give them the love and attention that they all deserve. Daily Basics Feed on time (follow the owner's instructions exactly—type of food, portion size, schedule) Fresh water always available Daily walks & exercise tailored to the dog’s age, breed, and energy level Bathroom breaks regularly, especially in the morning, after meals, and before bed 🧠 Mental & Emotional Care Playtime with toys or games they enjoy Affection & attention (petting, brushing, cuddles—if they like it) Stick to routine to reduce anxiety while their owner is away 🏥 Health & Safety Watch for signs of illness or distress (vomiting, limping, excessive barking, etc.) Give meds if needed (make sure you're trained and authorized) Keep dogs leashed or fenced—never assume recall is perfect
“Cynthia is amazing. Thoughtful, communicative, flexible. My dogs fell in love with her immediately and I felt such peace of mind knowing how well she was caring for my babies. Cynthia went well over above and beyond and I would recommend her to anyone who will listen. Thank you Cynthia!! 💚💚”
“Kayla was great! Followed all our instructions and sent tons of pics!”
“I had complete confidence in Kate since our first meet and greet with the pups. She took her time to earn their trust and the whole pack agreed she was the one.”
“Alisa was able to help lucky last minute and we are very appreciative. Thank you for taking such good care of him and sending pics.”
Loving house sitters in your neighborhood
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Kayla A.Star Sitter
“Kayla is an amazingly awesome sitter, she sent many pics keeping me updated thought out her stay watching our pets. She truly went above and beyond. Highly recommend!”
Callie L.
Star Sitter
“Callie did a fantastic job of caring for Maybel and our home while we were out of the country for an extended period of time. She treated our dog and our home as if they were her own. We got daily updates and photos too!”
Alex F.Star Sitter
“Alex and Christina were very sweet. They sent lots of updates and spent a lotttt of time with our separation-anxiety cat while we were away for the week, and she seemed perfectly content when we returned home! We were glad to have them to help us!”
Faith W.
“Faith was amazing! She took such great care of our dogs and her communication was so great! We were able to relax and know our dogs were taken care of while we were gone!”
ROSEMARY B.
“Great sitter. Rosemary sent photos and communicated frequently. Most importantly, she seemed to truly enjoy working with Sydney. Our dog can be a little difficult sometimes and we often come back to a dehydrated, depressed pup. She seemed to be in great spirits and that’s a credit to Rosemary. Would definitely recommend!”
Lauren S.Star Sitter
“Lauren was so great with our stubborn bull dog. She is excellent with communication and provided regular updates while we were gone which was so helpful. We knew our pup was in great hands with her. We would definitely recommend her!”
Abby G.
“Super sweet dog-sitter! The dogs loved her. And we appreciate her so much! Abby communicated well and set our hearts at ease. We were able to have a wonderful weekend away knowing the dogs were in great care with Abby. Will hire again!”
Katie B.
“Katie house sat for us and loved on our lab, Fran! She is probably one of the best communicators and sent frequent pictures and videos throughout our 6 day vacation. She was also kind, courteous, and trustworthy. We will definitely reach out to Katie for our next vacation when Fran needs care!”
Audrey B.
“Audrey (and her friend Devin) were amazing! She was very flexible with arrival and departure times for our Moose, a 3 year old pup, who loved playing with her fur baby, Duke, as well! She was able to stop by our home twice before the dates we needed her for to meet her and her fur baby and they were both very sweet. Audrey updated me while I was away to ensure my dog was okay and also was very great with giving him plenty of love and attention all throughout the day! Moose was very tired the next day so I know she got plenty of play time and exercise in during her stay. We came home to a clean house that was exactly how we left it. Audrey was overall was very accomodating, sweet, trustworthy, and made it very easy for me to feel comfortable leaving my pup. Thank you Audrey and Devin! Moose can't wait to see you again next weekend ?”
Perrin W.
“She took great care of my kitties while I was out of town! She sent pictures often and left my house in wonderful condition. I would absolutely trust her again to take care of my fur babies.”
Amber K.Star Sitter
“Amber was absolutely the best!! J never had to wonder how things were going, she kept me updated with pictures and videos the whole time. I think my pets like her more than me at this point- highly recommend and will definitely be having her pet sit for me again!”
Reilly F.
“Reilly was great! She sent updates and took great care of our dog! Will definitely book again.”
Jason K.
“Jason has watched my pups on several occasions. I have an elderly 14 year old pup, that moves a little slower, and Jason has all the patience with her on their walks as she enjoys sniffing all the things. He has also cared for my pup with epilepsy and provides snuggles and tennis ball plays to keep him engaged and his energy in check. I know my pups are well cared for and they enjoy Jason spending time with them as they are quick to greet him and bring him a toy to play with or belly up for some scratches and ear rubs. I highly recommend Jason if you need a pet sitter!”
Cynthia S.
“Cynthia is amazing. Thoughtful, communicative, flexible. My dogs fell in love with her immediately and I felt such peace of mind knowing how well she was caring for my babies. Cynthia went well over above and beyond and I would recommend her to anyone who will listen. Thank you Cynthia!! 💚💚”
Kayla J.
“Kayla was great! Followed all our instructions and sent tons of pics!”
Aymee S.
“Great communicator!”
Kate M.
“I had complete confidence in Kate since our first meet and greet with the pups. She took her time to earn their trust and the whole pack agreed she was the one.”
Alisa G.
“Alisa was able to help lucky last minute and we are very appreciative. Thank you for taking such good care of him and sending pics.”
Emma N.
“Emma is the best! Sherman loved loved loved being able to spend time with her! House was so clean & everything went perfect!”
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
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winchester on Rover as of Jul 2025 was about $45 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 Jul 2025, there are 1,487 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 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.
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