Pet Sitting in Winchester
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winchester pet sitters


“I highly recommend Jessica! Jessica does a wonderful job caring for pets! She videos her visits and keeps the owner posted in a timely manner. My quirky dogs enjoyed her visits so much! She provided scheduled medications and feedings and potty breaks as requested during stormy weather and hectic holiday schedules! How wonderful to be able to have our pets at home with someone so professional and reliable! We will call on her again”


“I love Kate! Very friendly and her communication is consistent. She constantly sent pictures and Bailey loved her. Definitely helped ease my nerves in leaving her behind. Will be using her again for sure.”


“I am always impressed with Barb's care for my 2 cats. She finds out their preferences and caters to them. She spends time both helping them feel comfortable with her for affection and plenty of play time. She is observant of behaviors and communicated each visit with many photos and updates. Plus, she is a pleasure to work with herself!”


“You can depend on Bella to arrive on time and to take great care of your animals & home. She communicates well and is a sweet, honest person. Bella treated my chickens and dog like they were her own.”



“Awesome is the perfect word to describe her! She was available last minute when my wife went into labor. She took such good care of our babies. Would recommend to anyone asking for pet care.”


“This was our first time looking for a sitter in MO and picked well! She addressed my main concern while gone which was locating the hiding cat-not an easy feat! We will definitely be using her again!”


“This was my first time using a pet sitter and it couldn’t have gone any better. Danny and Jennifer were wonderful! They’re very communicative and let me know exactly what was going on with my older dog and sent lots of pictures. It really set my mind at ease knowing she was being so well cared for. 10/10 would highly recommend them.”


“We recently hired Mason to take care of our Labrador, Jet, while we were away, and we couldn't be happier with his service. Mason was professional, caring, and went above and beyond to ensure Jet was well looked after. He provided us with regular updates and photos, which gave us peace of mind. Jet clearly loved spending time with Mason, and we returned to a happy and healthy pet. We highly recommend Mason to anyone in need of a reliable and loving pet sitter. He is truly a five-star caregiver!”


“Hollis is the best! I am a travel nurse, and am out of town half of the week. I’ve got 2 very elderly cats, each doing their own thing, and Hollis takes care of them every week. She is amazing with them. My cats love her and I always come home to them being happy and well cared for ❤️”


“Alicia was a great sitter. Took awesome care of our puppies and was an awesome communicator. She performed all the puppy duties and counted everything through rover including all the walks. I highly recommend Alicia!. Loved the pictures”


About: I have worked in dog care for multiple years and have again many skills from this. As well as gained a lot of exposure to different dogs and their needs! I do work at a dog kennel currently, but wanted to try something on my own but I would work this around my work schedule as I am only part time. Firstly I will always respect your space! I would love in-depth instructions to ensure no confusion. I will complete all tasks properly and meet all their needs. Their safety is most important as well as caring for them properly:)

“Susan took such great care of my little fur baby while I was away for the holidays. She kept me updated with her visits and I knew my little Kiwi was in a great, loving hands while I was gone. I highly recommend Susan if you want someone who truly loves dogs and who'll care for them like they're her own. I will be using Susan to car for my fur baby whenever I need to travel.”


About: Choosing someone to care for your dog is a big decision, and you want peace of mind knowing they're in capable, loving hands. I've had the pleasure of caring for many dogs over the years, both in their own homes and in mine. This experience has taught me how to truly care for dogs, making sure they feel happy, safe, and loved. You can rest assured your dog will be well-cared for, receiving plenty of attention, playtime, and comfort. Since I work from home, your dog seamlessly becomes part of my day! They'll get consistent attention and supervision because I'm around most of the time. This means no long stretches of being alone; instead, they'll be right in the mix of a lively, active household. We'll fit in plenty of potty breaks, playtime, and even just cozy lounging nearby while I'm at my desk. My schedule is super flexible, so it's easy to make sure they get their walks, meals, and individual play sessions right on time. When caring for pets, I treat them like part of the family—whether in my home or yours. I follow their usual routine, including feeding, walks, playtime, and any special instructions you provide. In my home, we have a fully fenced-in yard for safe outdoor play, and I can easily crate your dog if needed or requested. I provide a clean, secure, and comfortable environment where your pet can feel at ease. In your home, I’m respectful of your space while making sure your pet feels safe and loved. I also send regular updates with messages and photos so you can relax knowing your pet is in good hands.

About: I have been caring for dogs since I was just a pup! I have two babies of my own and understand the importance of having a trustworthy person to support them when you can’t. My dogs are members of the family and I can ensure that yours will be the same when they’re in our care. I am fluent in walking, stimulation, play and nurture. Please allow me to go on patrol when you need to pawz! I am a teacher, so I am available to cater to your babies on weekends full time, and have limited availability throughout the week. I have the summers off, so I am also available daily to give your babies the attention they deserve! We have a fenced in backyard at our home location and two of my own dogs to keep your baby busy! Our basement has a doggy designed space created with our fur babies specifically in mind. Your fur baby will be able to roam freely and enjoy our space both indoor and outdoor. I could also easily crate your baby if that is your wish.
Loving pet sitters in your neighborhood
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Alycia H.
Star Sitter


“Alycia did an amazing job taking care of my pups while I was away. She even came out during snow and freezing temperatures. I would definitely recommend her.”


Callie L.
Star Sitter


“Callie did a great job keeping us informed of her drop-in visits with our dog. We were happy to see the pics. We will book with Callie again!”




Jessica L.Star Sitter

“I highly recommend Jessica! Jessica does a wonderful job caring for pets! She videos her visits and keeps the owner posted in a timely manner. My quirky dogs enjoyed her visits so much! She provided scheduled medications and feedings and potty breaks as requested during stormy weather and hectic holiday schedules! How wonderful to be able to have our pets at home with someone so professional and reliable! We will call on her again”


Kiffin M.Star Sitter

“Excellent care and lots of TLC for our new puppy! Kiffin will treat your pet like her own! Will definitely request her again for future visits.”


Kate B.Star Sitter

“I love Kate! Very friendly and her communication is consistent. She constantly sent pictures and Bailey loved her. Definitely helped ease my nerves in leaving her behind. Will be using her again for sure.”


Barbara B.


“I am always impressed with Barb's care for my 2 cats. She finds out their preferences and caters to them. She spends time both helping them feel comfortable with her for affection and plenty of play time. She is observant of behaviors and communicated each visit with many photos and updates. Plus, she is a pleasure to work with herself!”


Amy N.Star Sitter
“Amy is lovely, caring, and flexible. I am so lucky to have found her to care for my super senior dog who can’t be alone anymore while we are away at work.”


Bella D.

“You can depend on Bella to arrive on time and to take great care of your animals & home. She communicates well and is a sweet, honest person. Bella treated my chickens and dog like they were her own.”




Nikki W.

“Awesome is the perfect word to describe her! She was available last minute when my wife went into labor. She took such good care of our babies. Would recommend to anyone asking for pet care.”


Paige W.

“This was our first time looking for a sitter in MO and picked well! She addressed my main concern while gone which was locating the hiding cat-not an easy feat! We will definitely be using her again!”




Charles F.


“Charles really knows his dog stuff! He was also readily available every last minute for my senior boy. I would recommend him to everyone nearby!”


Danny & Jennifer C.Star Sitter

“This was my first time using a pet sitter and it couldn’t have gone any better. Danny and Jennifer were wonderful! They’re very communicative and let me know exactly what was going on with my older dog and sent lots of pictures. It really set my mind at ease knowing she was being so well cared for. 10/10 would highly recommend them.”


Mason C.Star Sitter

“We recently hired Mason to take care of our Labrador, Jet, while we were away, and we couldn't be happier with his service. Mason was professional, caring, and went above and beyond to ensure Jet was well looked after. He provided us with regular updates and photos, which gave us peace of mind. Jet clearly loved spending time with Mason, and we returned to a happy and healthy pet. We highly recommend Mason to anyone in need of a reliable and loving pet sitter. He is truly a five-star caregiver!”


Hollis W.Star Sitter

“Hollis is the best! I am a travel nurse, and am out of town half of the week. I’ve got 2 very elderly cats, each doing their own thing, and Hollis takes care of them every week. She is amazing with them. My cats love her and I always come home to them being happy and well cared for ❤️”


Alicia S.Star Sitter

“Alicia was a great sitter. Took awesome care of our puppies and was an awesome communicator. She performed all the puppy duties and counted everything through rover including all the walks. I highly recommend Alicia!. Loved the pictures”


Finnley W.
“If you're looking for someone who will care for your pets like they’re her own, look no further than Finnley Wright. I have the privilege and honor of being Finnley’s mom and I can say without hesitation that she is one of the most dependable and hard-working people I know. Whether it’s showing up early, staying late, or going the extra mile to make sure everything is just right, Finnley brings a level of commitment that gives total peace of mind. What truly sets her apart, though, is her deep love and compassion for animals—especially dogs. She has a natural way with them, earning their trust quickly and treating them with the perfect mix of kindness, attentiveness, and playful energy. Finnley understands that pets are family, and she takes that responsibility seriously. If you want a dog walker or pet sitter who is reliable, loving, and absolutely trustworthy, Finnley is your person. Your pets will thank you!”


Susan K.Star Sitter

“Susan took such great care of my little fur baby while I was away for the holidays. She kept me updated with her visits and I knew my little Kiwi was in a great, loving hands while I was gone. I highly recommend Susan if you want someone who truly loves dogs and who'll care for them like they're her own. I will be using Susan to car for my fur baby whenever I need to travel.”


Cammie R.

“It was nice to be at ease while at our son’s wedding knowing our dogs were in good hands. Thanks Cammie!”


Blanca B.
“Blanca B. walked both of our dogs, and she was absolutely wonderful! She is super nice, caring, and attentive—our pups loved her right away. Blanca always made sure they were safe and happy during their walks, and she genuinely cares about animals. I highly recommend her to any pet parent looking for a trustworthy and loving dog walker. She’s truly an awesome human being!”


Hannah D.
“Hannah is an exceptional pet caregiver! With her attentive nature and genuine love for animals, she goes above and beyond to ensure pets are happy and well-cared for. Highly recommended!”
Winchester pet parents share their Rover experiences
Cynthia was awesome! We video chatted prior to the visits and my daughter showed her how to mix the food for Geico, the crested gecko. We also showed her the 2 tanks so she would know what to look for. Cynthia sent us pics from her visit which was appreciated. Since these drop ins were for 2 geckos Cynthia was the perfect person because she has a bearded dragon and experience with reptiles. Highly recommend Cynthia, especially if your pet is not the norm!

Ashley was AMAZING! Emi was very happy and very well taken care of. Ashley made sure to make some time for play and cuddles and was very responsive. She even went out of her way to clean anything in the space that needed cleaning up, took out the trash, and wiped Emi’s messes without me asking. Super trustworthy and a fantastic experience!

We were very pleased with how Connor took care of our almost 17-year old dog. He was responsible, easy to work with, took initiative and his communication was excellent. His daily updates and pictures gave us peace of mind while we were gone. We will be happy to have him take care of Benji in the future.

I was worried about letting a stranger watch my dog but my fears were settled the first day. She obviously loves animals. She sent great pictures of them having fun and left me some Polaroid pictures with a nice thank you card the first day. The rest of the week went great to. She showed up at the right time and spent extra time with him. Did everything I asked her to do and we communicate great about needs my dog had during the week. I highly recommend her.

Taylor is absolutely wonderful! We are really looking forward to having her watch our dogs and cats while we’re away on vacation, and wanted to have her come and hang out with them for a drop in - she made time for us, played with our pups and helped me feel so much more relaxed about being away from our babies for a whole week. I’m so grateful that we found her!

Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. 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 pet sitting in Winchester is $20
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 pet 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 6 repeat pet sitting clients
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winchester on Rover as of Aug 2025 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 525 pet sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 86% of Winchester pet sitters respond in under an hour.
Pet sitters in Winchester have an average of 17 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winchester.
Rover makes it easy to find Winchester pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 525 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 100% of pet sitters offer daily exercise, 97% offer medication administration, and 97% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
