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

“Justin helped us out on super short notice. He was very attentive, caring, and provided lots of updates and pictures. It’s clear he cares about pets and we’re super glad we found him! Highly recommend!!”


“Super happy with how communicative Loren was. She was patient with my little princess and spent a lot of time playing with her. I will definitely recommend Loren as well as book her again!”


“Hunter went above and beyond while caring for our three cats for this past week. When the storm was approaching, she texted me to see if I wanted her to put our water bowls in case the power went out. It did, and she did put water out. From the pics, I could tell that Emma warmed up to Hunter right away. Iris got her pills even though she was skittish. Thank you, Hunter, for taking care of the kids.”


“Theresa was great! We felt supported so we could enjoy a huge family event and not worry about our pups. She came on time and took them for a walk and tucked them back in. We highly recommend her.”



“We're so glad we were able to book Kristy and Chris to do drop-ins for our cat while we were on vacation over the weekend. Kristy and Chris were extremely professional and took detailed notes on the instructions to care for Pemi. We really appreciate their courtesy and timeliness. Would highly recommend them to anyone else in the area!”


About: I’ve taken care of my personal dogs as well as friends and family dogs for years now. I am experienced with dogs of all sizes, as well as all personalities. I am familiar with low energy and high energy breeds, and know how to cater to each of them. I also specialize in dogs that have anxiety as well as reactivity, and know how to monitor their behavior and understand them in a way that most humans and other animals do not. I currently work full time, Monday-Friday so all animals would need to be able to be home alone for around 8-9 hours during the weekdays. My current hours are 6:30am-3pm, so I make a point to be available in the morning before I leave for work, and then after I return from work. This also applies to drop-ins. I make a point to be fully available on weekends since I am away often during the weekdays, but am also home early enough during the week that I can spend the afternoon, evening, and night with your furry little ones. I will care for your pets by following the owners’ and pets’ needs, I never stray from instructions. I will ensure safety precautions are always taken, as your animals safety is my highest priority.

“My husband and I knew upon meeting Tara for the first time that she was the perfect fit with our cat, Charlie. Charlie is very shy and usually hides when people come to visit. However, this was not the case when Tara entered our home. Tara did a top-notch job taking care of Charlie during her drop in visits over a period of one month. We were so happy when she sent up pictures and updates. Tara is reliable, kind, professional, and a true animal lover. Cats can be messy with the litter, etc. But with Tara on the job, we came home to a very neat home and well-fed, content cat. We will definitely seek Tara services again. Furthermore, we highly recommend her. Thanks a million, Tara.”


“Karina has been a wonderful caregiver to Dex! She goes above and beyond for him. She thinks of everything and makes sure he is always well taken care of. I have found her to be very reliable and professional and would recommend her to anyone! She is very thoughtful and thorough in all that she does, 5 stars!”

About: I'm available to provide the best care for all your furry (or fur-less), scaly, and or feathered friends. I understand that each pet has unique needs, from daily walks and belly rubs for dogs to creating the perfect habitat for reptiles and keeping your cat’s world enriched with toys and cuddles. I offer compassionate care tailored to your pet’s specific personality and requirements, ensuring they feel loved, safe, and happy while you're away. No matter the species, I treat every pet like they’re part of my own family, with lots of attention, patience, and of course, treats! I'm currently working and going to school part-time, but feel free to reach out and I'll see what I can do to help you out! I always prefer to provide care in your home, and will treat your home, property and of course your pets with the upmost respect. In addition to caring for your pets, I am happy to bring in the mail or delivered packages, and provide other random services at your request as needed. I may be able to provide boarding care in my home with notice on a case by case basis provided your pet is house-trained and gets along well with my personal pets.

“Rhys is the best!!! Our little high energy spoiled baby was happy as could be when we got home, it’s obvious he was very comfortable and relaxed and loved Rhys. They had great playtime, but also calm down time, which is perfect because he can be easily overwhelmed. Rhys obviously loves animals and has the perfect temperament and patience to really “read” them. We felt very comfortable while we were out and we HIGHLY recommend Rhys; a confident, smart and very sweet new friend for our crazy little dude.”


About: Hi, I'm Rusty! I've spent my entire life caring for dogs and truly believe that pets are family, deserving only the best walks and care. With experience handling a wide variety of breeds, sizes, and needs, I’m ready to offer your dog the attention they deserve. As a recent retiree, I now have the time and passion to help your pups live their best life! 🐶 I have recently retired, so I have a very flexible schedule! I am available for dog walks and drop-in visits on weekdays between 8:00 A.M. and 3:00 P.M. I treat dogs with the same love and care as any family member. Each day, I ensure they receive plenty of attention, exercise, and affection. Whether it's a morning walk or playtime in the yard, I make sure they’re always happy and comfortable. I am attentive to their individual needs, providing them with a routine that keeps them healthy and active. I also make sure the dogs have fresh water at every visit. Above all, I believe in building a strong bond based on trust, love, and mutual respect, making sure they feel safe and loved every single day.


“Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.”


About: I have a very loving home, Calm, never any yelling. I take pride on our home. I am always willing to make things work and as stressless as possible. I know it can be very hard to leave your fur baby. I am available all hours of the day to chat to make you and your fur baby feel comfortable I work from home full time, I own a septic business. My office is right in my home. If you Choose for me to come to your house, I have open availability as well. I will take very good care of your pet if it’s in my home or your home. I have two small dogs myself. We are always on walks, outside, food and water are always available. If we were to come to youtr home, i will always follow the routine you lay out for me. I will never guess on things i will always have you if i am unsure of something.

About: I have been around dogs my whole life, I took animal science in High school and worked in dog related jobs for about 5 years. I currently have five of my own fur babies. 3 pups and 2 cats I currently am out of work for the summer and I have open availability. Late August I will return to work as a preschool teacher and will be available evenings and weekends. I will take care of your dog as if they were my own, following all the requirements that you set up before hand. Giving your dog all my attention and love.

About: Have loved and had dogs my whole life and hike with them daily!! In the summer we also take daily swims in the river! Nighttime is snuggle time on the couch with the fur children! I work flexible hours on my flower farm and dogs have access to in and outside at all times. I always make time for a walk or a swim with the fur babies I have 2 super friendly dogs…a pug and a lab and they LOVE making new friends! We have an electric fence and extra vibration collars if needed

About: I have worked in veterinary medicine since 2017 (and still do) work at a specialty hospital! Caring for animals comes natural to me. Having the background and knowledge in this field will help you to feel confident with your loved ones in my care. I work a very flexible schedule, and I am available on the weekends as well. Plenty of play time. Lots of walks, naps & snuggles. My Rudy boy and I run together, I take him to the dog park on the weekends and if we don’t get too we absolutely MUST play ball or tug of war and we’re outside in the yard. He is crate trained and is comfortable there during my work hours and is on my bed at night. I will fit the needs of the client based on their lifestyle. Whatever is most comfortable for clients is the care I want to deliver all of which can be discussed. I hope to make the time spent away from your baby stress free knowing he/she is getting all the love and attention from Rudy and I. Photos and videos included of course!

About: Hi everyone, I’m Amanda! Currently a stay at home mom raising my 5 and 6 year old human children, and my 7year old mix and crazy kitten! We’re all avid hikers and nature lovers, being outside is our absolute favorite! I grew up having dogs, mostly mixes and rescues, so I know how to gently approach pets that may have trust issues or who may be shy. With our mix having husky in her, I know all about high energy and how to get them relaxed and sleepy! Walking, running, and hiking are what we use to personally exercise our dogs so I can make sure whatever works best for your pup is what we’ll do! If needed I can be open to at home boarding, but I would first need to be sure they’d get along with my dogs :) Thank you for reading! I'm currently home full time with my kids in school, so I'm available from 9A - 2P (depending on distance) and after 5 during the week, as needed on the weekends. We have a large yard, and lead available for dogs who may need it. Currently our dog does well to stay on our property, she loves walking down to the brook for a dip!
Loving pet sitters in your neighborhood
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Justin P.Star Sitter

“Justin helped us out on super short notice. He was very attentive, caring, and provided lots of updates and pictures. It’s clear he cares about pets and we’re super glad we found him! Highly recommend!!”


Loren V.

“Super happy with how communicative Loren was. She was patient with my little princess and spent a lot of time playing with her. I will definitely recommend Loren as well as book her again!”


Hunter F.Star Sitter

“Hunter went above and beyond while caring for our three cats for this past week. When the storm was approaching, she texted me to see if I wanted her to put our water bowls in case the power went out. It did, and she did put water out. From the pics, I could tell that Emma warmed up to Hunter right away. Iris got her pills even though she was skittish. Thank you, Hunter, for taking care of the kids.”


Kristen N.

“Kristen was great..my dog Gabe loves her..I would highly recommend her..”


Theresa C.Star Sitter

“Theresa was great! We felt supported so we could enjoy a huge family event and not worry about our pups. She came on time and took them for a walk and tucked them back in. We highly recommend her.”




Kristy & Chris B.


“We're so glad we were able to book Kristy and Chris to do drop-ins for our cat while we were on vacation over the weekend. Kristy and Chris were extremely professional and took detailed notes on the instructions to care for Pemi. We really appreciate their courtesy and timeliness. Would highly recommend them to anyone else in the area!”


Paige R.
“Paige has a wealth of experience with reactive dogs and is patient and understanding with all types of animals. She is reliable, consistent and communicates as much or as little as requested. I have no hesitations in recommending Paige to pet and/or house sit.”


Tara N.Star Sitter

“My husband and I knew upon meeting Tara for the first time that she was the perfect fit with our cat, Charlie. Charlie is very shy and usually hides when people come to visit. However, this was not the case when Tara entered our home. Tara did a top-notch job taking care of Charlie during her drop in visits over a period of one month. We were so happy when she sent up pictures and updates. Tara is reliable, kind, professional, and a true animal lover. Cats can be messy with the litter, etc. But with Tara on the job, we came home to a very neat home and well-fed, content cat. We will definitely seek Tara services again. Furthermore, we highly recommend her. Thanks a million, Tara.”


Karina S.
Star Sitter

“Karina has been a wonderful caregiver to Dex! She goes above and beyond for him. She thinks of everything and makes sure he is always well taken care of. I have found her to be very reliable and professional and would recommend her to anyone! She is very thoughtful and thorough in all that she does, 5 stars!”


Jesse R.
“I can't say enough good things about Jesse! He took amazing care of my dog and cat, while I was away. My puppy can be energetic, and my cat has specific needs, but Jesse handles everything with patience, care, professionalism, and he is trustworthy. He shares regular updates, photos, and could I could tell my pets were in loving hands. He will treat your animals like family. No matter what kind of pet you have, you can feel confident that they will be well cared for. Highly recommend!”


Rhys M.

“Rhys is the best!!! Our little high energy spoiled baby was happy as could be when we got home, it’s obvious he was very comfortable and relaxed and loved Rhys. They had great playtime, but also calm down time, which is perfect because he can be easily overwhelmed. Rhys obviously loves animals and has the perfect temperament and patience to really “read” them. We felt very comfortable while we were out and we HIGHLY recommend Rhys; a confident, smart and very sweet new friend for our crazy little dude.”


August "Rusty" N.
“I enthusiastically recommend August, AKA Rusty, for any and all pet care needs. Rusty loves and cares for every four-legged friend he meets. Rusty is a kind and compassionate person. He is a dog advocate. One of my puppers is selective when it comes to liking humans, especially men, but he loves Rusty. I feel at ease when Rusty is interacting with my dogs as I know they are in good company. I would not hesitate in trusting Rusty with my four-legged family members. Dogs live their best lives when Rusty is around!!!”




Lynsey M.

“Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.”


Stacey G.

“Stacey was great. She even managed to get my very shy cat to come out from her hiding spot. I would definitely have Stacey take care of my Cat again”


Danielle L.
About: I have a very loving home, Calm, never any yelling. I take pride on our home. I am always willing to make things work and as stressless as possible. I know it can be very hard to leave your fur baby. I am available all hours of the day to chat to make you and your fur baby feel comfortable I work from home full time, I own a septic business. My office is right in my home. If you Choose for me to come to your house, I have open availability as well. I will take very good care of your pet if it’s in my home or your home. I have two small dogs myself. We are always on walks, outside, food and water are always available. If we were to come to youtr home, i will always follow the routine you lay out for me. I will never guess on things i will always have you if i am unsure of something.


Katie O.
About: I have been around dogs my whole life, I took animal science in High school and worked in dog related jobs for about 5 years. I currently have five of my own fur babies. 3 pups and 2 cats I currently am out of work for the summer and I have open availability. Late August I will return to work as a preschool teacher and will be available evenings and weekends. I will take care of your dog as if they were my own, following all the requirements that you set up before hand. Giving your dog all my attention and love.


Erinn H.
“I’ve known Erinn for over 20 years, and she is truly one of the most loving and responsible pet owners I know. She has cared for my dogs (and even my snake!) many times. Erinn takes my dogs and her dogs on hikes and swims and makes sure they’re happy, healthy, and well-loved. Erinn has experience with small breeds, big high-energy dogs, and even animals with special needs. She goes above and beyond, even making her own dogs’ food from scratch. Most of all, she’s compassionate and trustworthy. Seeing how she loves my animals like she loves her own is what makes Erinn truly exceptional. I would recommend her to anyone without hesitation.”


Danyelle G.

“Dany was the best - kind and accommodating and cared for my kitty like it was her pet!”


Amanda I.
“Amanda was very in depth when it came to getting to know my pup Rocco, she’s been walking him for years now when we are out of town and would highly recommend her to anyone in the area. Always on time and gives our pup the attention he needs when we are not home. 10/10 !!!”


Amanda B.
“Amanda has gone above and beyond with the care that she has given to my dog. Our puppy can't wait for Amanda to arrive and will whine and cry until she reaches the door! She enjoys the long walks she goes on with Amanda and comes back tired and content. I highly recommend Amanda's services.”
Winchester pet parents share their Rover experiences
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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
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The median cost per night for pet sitting in Winchester is €25
Why Choose Rover?
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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 4 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 €25 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 152 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, 90% of Winchester pet sitters respond in under an hour.
Pet sitters in Winchester have an average of 14 years of experience. Pet sitters with repeat customers have an average of 4 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 152 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, 100% offer medication administration, and 100% 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.
