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

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Top rated Winchester pet sitters

“They were absolutely amazing! Savanna’s husband was a huge help. Our doggos are our babies and our big boy got a pretty nasty ear infection and they sent a lot of photos to us, to reassure us he was fine. Our cat even came out to visit. He’s super skittish around anyone including us and he was coming out to visit each time. We loved them definitely will use them again for our next adventure!”


“Emily took amazing care of our darling, and needy ;) cat Nikka. She went above and beyond to make sure Nikka had the necessities each day and that included serious and extended cuddles. This was our first time using Rover and I’m so glad that Emily took such great care of our girl. We highly recommend.”


About: I’ve taken care of dogs ever since I can remember, owned them from a young age, and helped my grandma take care of her many pets. I’ve been lucky enough to help take care of family members, neighbors, and friends animals, and I would be so excited to get the chance to meet yours! I have a very flexible schedule, I do work another job at fortune wok but it is very flexible if scheduled even a day or two in advance. I try to be as respectful as possible to the space and keep the dog entertained in a confined area wether that be in the backyard or living room. And other then that I do the best I can to have fun with the dog and have it enjoy it’s time.

About: Animals have always had an extremely special place in my heart. Ever since I was a kid I’ve helped care for my family’s own pets: feeding them, caring for their health, giving baths, taking them outside and on walks, and pretty much anything else having a pet entails. I also am in the process of beginning volunteering with the cats and dogs at Lawrence Humane Society! I am a full-time student, but I am available whenever I am not busy with classes. I also have a few volunteering shifts throughout each week that I need to work around, and a job (that I will be done with next month). I provide them with food and water, clean up their litter, play with them, take the dogs on walks, and show all the animals lots of love! I am also flexible and open to doing whatever I am able to.


About: I love dogs. I have always rented and never had an opportunity to own my own pets. Rover will give me a chance to get my pet fix in. Here in a few months I will be able to work from home 2 days a week. In the meantime, I am available mornings, during my hour lunch break, and after work during the week. I have flexible availability on the weekends. I treat clients homes how I would want my own home to be treated. I will always leave a home better than I found it. I pay close attention to detail and will go above and beyond for your pet.

“We’ve used Skylar twice now and both times have been so awesome. She communicates clearly with the visits and takes great care of our dog and cats, two of who are very senior and require special medication and treatment. They love her and were comfortable with her even the super shy one! Highly recommend.”


About: My name is Chelsea. I am married and have two daughters and a son. They are 10, 6, and 3. I have a wonderful German Shepherd and a 20 pound cat named Karen. We love caring for other animals. We also live on three acres so there is plenty of room to run and play! I can come to your home or board in ours. We are very active individuals. Both my husband and I are runners. Just let me know if you have anymore questions and I would be more than willing to answer them! We are very flexible with our schedules. My husband works full-time, but I drive for Uber so I can make my own schedule when needed. We try to stay as active as possible and play with pets in the home. We have a German shepherd that loves the extra play time!

About: Hello! I’m Jordan and I’ve been surrounded by animals my whole life, thanks to my mom being a dog groomer and breeder. From attending flyball competitions and dog shows to pet sitting during high school, I’ve developed a deep love and understanding for animals of all kinds. I currently have a cat of my own, so I’m well-versed in caring for different types of pets. Originally from South Florida, I’m using the income from this app to support my graduate school journey. Your pet will be in loving, experienced hands, and I’m excited to offer my care and attention to your furry friend! My schedule is usually pretty flexible. Message me and I'm sure we can set something up. Looking forward to care for and play with your doggies. I tend to follow the owners instructions since they are the experts of their fur babies comfort. I treat every animal as if they were my own.

“Natalie was great! She took our last minute holiday booking request and our cat and dog seemed very happy with her visits. It was nice to get daily updates and photos of the critters. We squeezed in a meet and greet so everyone could get acquainted and go over routines. Thanks!”

About: I am a nanny 3 days a week. Other than that, I am home all day everyday, I have tons of open availability to give your pets the love they deserve! I have been watching dogs from a very young age ! My sisters dad owns a dog training company so I was raised around dogs! I work Mondays from 7-4, Thursdays 11-7 but won’t be working Thursdays started in August. Fridays I work 7-4. I am home around those hours and have fully open availability! I have a giant fenced in backyard! Friendly neighbors with friendly pets and a safe and friendly neighborhood to walk the dogs in! I have 4 roomates as well so there is always someone home!

About: I am a canine enrichment coordinator at a boarding facility and I teach basic and intermediate manners training classes. I have a degree in behavior science and I'm hoping to complete my KPA training certification in the near future. Ask about enrichment and basic training add-ons! I work as a full-time enrichment coordinator and dog trainer. As such, I have restricted availability. In general I am free Monday, Tuesday, and Friday evenings and all day on Saturdays. I am available for dog walking, check-in visits, and house sitting. I can also offer enrichment and basic training services as add-ons. Let's talk about some enrichment strategies to help your dog live a happy and full life!

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.

“Tara was great! She completed all tasks very well. She left my house neat and clean w dishes done and garbage and recycling taken out. I’ve only used 3 other pet sitters and she was by far the best! We had a little difficulty communicating and operating around the bitter cold, snow and ice conditions, but she rallied. Tara is personable and conscientious - I would definitely book her again.”


About: Hello pet parents my name is Octavia (i prefer to go by my middle name)! I HAVE EXPERIENCE WITH MORE THAN JUST DOGS AND CATS SUCH AS CHICKENS AND DUCKS !! I am military and I am able to access base when needed. I am 20 years old and I LOVE animals!! Due to my Army career I live in a lot with my wife, my dog, and my kitten. Taking care of animals is my calling! I have now been in the Army for two years. I joined to further pursue my college education and become a veterinarian in the future. Iam extremely passionate about the care that animals receive. I have volunteered for lots of shelters since i was young to learn all about animals and their needs, so it is my duty to ensure that your fur baby is well taken care of. Being that i worked with a lot of trained animal handlers, I have experience with animals who have many special needs such as diabetes, aids, cancer, seniors, etc. I also have experience with many different ages and breeds of dogs/cats. I previously worked at a groomers and volunteered at a pet shelter. At both establishments I fed the animals, bathed them, played with them, and took them out for restroom breaks. | love to stay active so I go on a daily walk/run and I would love for your pet to accompany me. I have plenty of room in my schedule to spend quality time with your pet. This would include going to the park, play time, and even cuddle time! While you are gone from your sweet fur baby, I will be available for communication 80% of the time. I am more than happy to send updates on how your pet is doing upon request. Anything that makes you and your pets comfortable I am more than happy to do. The less stress there is for you and your fur baby the better! I am here for your needs!! I am extremely excited to be pet sitting again as l did this before I joined the military. I work from 9-5 for the time being until my shift changes but am truly excited to be able to rush home and care for your pets. I will always keep you updated on my schedule being that my hours change every 3 months. I have a dog and a kitten right now and I constantly do research on their diet and behavior and their well being to make sure I am giving them the best possible life that they deserve.

About: I’ve been loving and taking care of animals all my life. I’ve loved them since I was a baby. I try to save every stray! I’m retired and looking for something to do that brings me joy and this is it. I’m available anytime during the day and the evening I will be caring for pets in other peoples homes but I have a fenced yard for my babies but monitor their time in the heat and cold.

About: I have an immense love for animals and treat my own as if they were my children, giving them endless care, respect, and affection. Their happiness and well-being are my top priorities, and I go above and beyond to ensure they feel safe, loved, and understood. This deep connection extends to every pet I care for, making me an exceptional pet sitter. I am patient, responsible, and attuned to each animal’s unique needs, whether it’s playtime, special diets, or just providing comfort. My dedication and genuine passion for animals make me someone pet owners can trust completely. I am always at home. I do work from home. But that is a few hours per day and my schedule can be adjusted to the needs of any animal. I have a lead setup but all dogs will be taken on multiple walks a day. During bed time they would be with me unless requested by owner to be crated.

About: I come from a farm happy family and managed a doggy daycare, with extensive work in animal rescue. I have dealt with just about any animal you can imagine. Dogs, cats, horses, goats, guinea pigs, fish, snakes, birds, etc. Not only that but I also have two fur baby's of my own, a black lab and a golden retriever. I have had my lab since he was about 2, and my golden retriever I got when she was about 12 weeks old. I love animals and am just looking to fill some of my free time and earn a little extra cash. My lab has since passed due to old age in 2019 but my golden loves the occasional company! I do work M-F and would be out of the home from 715am-5pm. I work full time for a nonprofit in Ottawa, so I am out of the house from 715am-5pm. I love going on walks and being outside before and after work! On the weekends aside from some errands I would be around. I take animal safety very seriously, especially after managing a doggy daycare, things can be unpredictable. I take extreme caution, and pay attention to all the signs your pet is giving me along with your requests to ensure they have a fun, safe time while in my care.

About: I'm grew up life at farm which with many animals. I love pets. There many story to telling. It can't explain.:) just ask me any.:) I work at home and I am always free and take my dog for a walk! I love to walk too which is known we me busy and I make a dogs happy and dogs make me happier! My parent has a big fence back yard. So the dog can play, enjoy, and be free! I always walk through the forest too and I can take the dog with me to hike on leash too in back forest tho!

About: I personally have had a lot of pets that have been properly loved and taken care of by me all of my life, this will be a great opportunity! I am a stay at home mom so this works perfectly to keep my busy! My little loves all kinds of animals! she will be a big help! I am very good when it comes to learning the animals language and will give and get what they need! I am very active when it comes to pets!
Loving pet sitters in your neighborhood
Search Results


Savannah A.

“They were absolutely amazing! Savanna’s husband was a huge help. Our doggos are our babies and our big boy got a pretty nasty ear infection and they sent a lot of photos to us, to reassure us he was fine. Our cat even came out to visit. He’s super skittish around anyone including us and he was coming out to visit each time. We loved them definitely will use them again for our next adventure!”


Ryan D.

“Ryan was very communicative and I can tell Asic enjoyed his time! Thanks, Ryan!”


Emily F.

“Emily took amazing care of our darling, and needy ;) cat Nikka. She went above and beyond to make sure Nikka had the necessities each day and that included serious and extended cuddles. This was our first time using Rover and I’m so glad that Emily took such great care of our girl. We highly recommend.”


Broderick S.
About: I’ve taken care of dogs ever since I can remember, owned them from a young age, and helped my grandma take care of her many pets. I’ve been lucky enough to help take care of family members, neighbors, and friends animals, and I would be so excited to get the chance to meet yours! I have a very flexible schedule, I do work another job at fortune wok but it is very flexible if scheduled even a day or two in advance. I try to be as respectful as possible to the space and keep the dog entertained in a confined area wether that be in the backyard or living room. And other then that I do the best I can to have fun with the dog and have it enjoy it’s time.


Gwyneth H.
“Gwyneth has been around all kinds of animals her entire life including dogs, cats, fish, and even a turtle. She is a a loving individual that believes in the care of all sentient beings. She has managed a busy work and class schedule successfully demonstrating her commitment and accountability.”




Kaley T.
“Kaley is a godsend! She is the best pet sitter that we have ever used. She really put us at ease while on vacation so many states away. I know that in Kaley’s hands, my fur babies will be safe and cared for. 12/10 would recommend. We’re lifelong customers!!!”


Skylar C.

“We’ve used Skylar twice now and both times have been so awesome. She communicates clearly with the visits and takes great care of our dog and cats, two of who are very senior and require special medication and treatment. They love her and were comfortable with her even the super shy one! Highly recommend.”


Chelsea L.
About: My name is Chelsea. I am married and have two daughters and a son. They are 10, 6, and 3. I have a wonderful German Shepherd and a 20 pound cat named Karen. We love caring for other animals. We also live on three acres so there is plenty of room to run and play! I can come to your home or board in ours. We are very active individuals. Both my husband and I are runners. Just let me know if you have anymore questions and I would be more than willing to answer them! We are very flexible with our schedules. My husband works full-time, but I drive for Uber so I can make my own schedule when needed. We try to stay as active as possible and play with pets in the home. We have a German shepherd that loves the extra play time!


Jordan P.
About: Hello! I’m Jordan and I’ve been surrounded by animals my whole life, thanks to my mom being a dog groomer and breeder. From attending flyball competitions and dog shows to pet sitting during high school, I’ve developed a deep love and understanding for animals of all kinds. I currently have a cat of my own, so I’m well-versed in caring for different types of pets. Originally from South Florida, I’m using the income from this app to support my graduate school journey. Your pet will be in loving, experienced hands, and I’m excited to offer my care and attention to your furry friend! My schedule is usually pretty flexible. Message me and I'm sure we can set something up. Looking forward to care for and play with your doggies. I tend to follow the owners instructions since they are the experts of their fur babies comfort. I treat every animal as if they were my own.


Natalie S.
“Natalie was great! She took our last minute holiday booking request and our cat and dog seemed very happy with her visits. It was nice to get daily updates and photos of the critters. We squeezed in a meet and greet so everyone could get acquainted and go over routines. Thanks!”


Lauren S.
About: I am a nanny 3 days a week. Other than that, I am home all day everyday, I have tons of open availability to give your pets the love they deserve! I have been watching dogs from a very young age ! My sisters dad owns a dog training company so I was raised around dogs! I work Mondays from 7-4, Thursdays 11-7 but won’t be working Thursdays started in August. Fridays I work 7-4. I am home around those hours and have fully open availability! I have a giant fenced in backyard! Friendly neighbors with friendly pets and a safe and friendly neighborhood to walk the dogs in! I have 4 roomates as well so there is always someone home!


Matthew P.
“Matt is amazing with dogs! His professional experience with canine behavior and training really shows when he is interacting with your pet. He is attentive to your dog’s needs and will go above and beyond to make sure they are happy and well cared for!”


Marilyn O.Star Sitter
“Your pets could not be in better hands! Marilyn is one of the most loving and caring pet sitters I have ever known. She has had pets her entire life and her love for them and all animals is extremely evident. I have left my animals with her more times than I can count and I always feel so comforted knowing how well cared for and loved they are when they're in her home. Our two dogs are always so excited when they hear that they get to go spend some time with Marilyn and her family. I highly recommend Marilyn and her home as a safe and loving place for your furbabies.”


Tara N H.

“Tara was great! She completed all tasks very well. She left my house neat and clean w dishes done and garbage and recycling taken out. I’ve only used 3 other pet sitters and she was by far the best! We had a little difficulty communicating and operating around the bitter cold, snow and ice conditions, but she rallied. Tara is personable and conscientious - I would definitely book her again.”


Tori T.
About: Hello pet parents my name is Octavia (i prefer to go by my middle name)! I HAVE EXPERIENCE WITH MORE THAN JUST DOGS AND CATS SUCH AS CHICKENS AND DUCKS !! I am military and I am able to access base when needed. I am 20 years old and I LOVE animals!! Due to my Army career I live in a lot with my wife, my dog, and my kitten. Taking care of animals is my calling! I have now been in the Army for two years. I joined to further pursue my college education and become a veterinarian in the future. Iam extremely passionate about the care that animals receive. I have volunteered for lots of shelters since i was young to learn all about animals and their needs, so it is my duty to ensure that your fur baby is well taken care of. Being that i worked with a lot of trained animal handlers, I have experience with animals who have many special needs such as diabetes, aids, cancer, seniors, etc. I also have experience with many different ages and breeds of dogs/cats. I previously worked at a groomers and volunteered at a pet shelter. At both establishments I fed the animals, bathed them, played with them, and took them out for restroom breaks. | love to stay active so I go on a daily walk/run and I would love for your pet to accompany me. I have plenty of room in my schedule to spend quality time with your pet. This would include going to the park, play time, and even cuddle time! While you are gone from your sweet fur baby, I will be available for communication 80% of the time. I am more than happy to send updates on how your pet is doing upon request. Anything that makes you and your pets comfortable I am more than happy to do. The less stress there is for you and your fur baby the better! I am here for your needs!! I am extremely excited to be pet sitting again as l did this before I joined the military. I work from 9-5 for the time being until my shift changes but am truly excited to be able to rush home and care for your pets. I will always keep you updated on my schedule being that my hours change every 3 months. I have a dog and a kitten right now and I constantly do research on their diet and behavior and their well being to make sure I am giving them the best possible life that they deserve.


Karla C.
“Karla is one of the most thoughtful, caring, and considerate people I've ever met, rather it be our grandkids or our fur babies! Awesome lady!”


Kasey L.
About: I have an immense love for animals and treat my own as if they were my children, giving them endless care, respect, and affection. Their happiness and well-being are my top priorities, and I go above and beyond to ensure they feel safe, loved, and understood. This deep connection extends to every pet I care for, making me an exceptional pet sitter. I am patient, responsible, and attuned to each animal’s unique needs, whether it’s playtime, special diets, or just providing comfort. My dedication and genuine passion for animals make me someone pet owners can trust completely. I am always at home. I do work from home. But that is a few hours per day and my schedule can be adjusted to the needs of any animal. I have a lead setup but all dogs will be taken on multiple walks a day. During bed time they would be with me unless requested by owner to be crated.


Nicole M.
“Nicole was amazing with my 3 dogs. I had a last minute business trip to Michigan and she was able to come and do over night stays. She send me pictures of them going on walks, playing in the backyard, at the dog park, and just hanging out in the house. They seemed very happy to have her there, and even sad to see her go! Definitely someone I will use in the future, she was awesome.”


Tiffany M.
About: I'm grew up life at farm which with many animals. I love pets. There many story to telling. It can't explain.:) just ask me any.:) I work at home and I am always free and take my dog for a walk! I love to walk too which is known we me busy and I make a dogs happy and dogs make me happier! My parent has a big fence back yard. So the dog can play, enjoy, and be free! I always walk through the forest too and I can take the dog with me to hike on leash too in back forest tho!


Kaylee C.
About: I personally have had a lot of pets that have been properly loved and taken care of by me all of my life, this will be a great opportunity! I am a stay at home mom so this works perfectly to keep my busy! My little loves all kinds of animals! she will be a big help! I am very good when it comes to learning the animals language and will give and get what they need! I am very active when it comes to pets!
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 $16
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 5 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 $16 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 60 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, 81% of Winchester pet sitters respond in under an hour.
Pet sitters with repeat customers have an average of 5 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 60 pet sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened 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.
