Pet Sitting in Winchester Village
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 Village pet sitters

“You’re the best!! We can’t thank you enough for taking such great care of our puppy. It seems like he has so much fun with you. Love all of the photos you send. Thank you. So grateful we found you.”


“Thank you sooo much! Vinny was well cared. Eileen sent photos and specific details about what Vinny did and the time frames she was with him. I'm so excited to know that Eileen is such a great pet sitter!”


About: I have taken care of animals all my life in all stages of life. I very much enjoy playing and running around with dogs and cats Im a Stay at home mom and unemployed looking for work and a work out I love animals so I'm excited to start hanging out with all animals I have a well trained dog who is crate trained while I'm gone so ik how to use a crate properly. I love to play and cuddle with all animals can't wait to meet your fur baby

About: I’ve been around animals all my life, & I can’t wait until I’m in a situation when I can finally have my own dog again. I’m knowledgeable about pet care & animal behavior, have great attention to detail, & enjoy learning more. I love every critter I meet (although I am partial towards chihuahuas & pits) & I have yet to meet a dog that didn’t like me. My family always had dogs growing up, & I have experience caring for a variety of dogs of different ages. I’ve only had two pet dogs that went through their entire life cycle with me, & my most recent doggo was a shitzu who came to me when she was 11. I spent her last few years trying to make her as comfortable & happy as possible. That’s the goal for every animal I care for. While this is obviously a job, & I do need the money, I genuinely enjoy getting to be helpful, to make someone’s life easier, & to, of course, spend time with dogs. I figure if I have to have a side hustle, it should at least be rewarding!! Thanks for reading!! I am a waitress- I usually work full-time, but it’s the slow season & we have a server surplus at the moment. I’m currently only scheduled for 3 night shifts a week, so my schedule is pretty open. Even on the days I do work, I would be able to check-in & care for the dogs before I go in, & can check on them afterwards as well if needed. Basically, I currently have plenty of time to fit in pet care. I am comfortable staying at someone else’s place; it would be nice to have a change of scenery every once in a while. Of course, I will treat your house with respect & be sure to leave it as it was when I arrived! If they wanna chill & sleep, that’s fine with me, but if they’re really active & need to play, I will play fetch & tug-o-war for hours on end. I have a car & supplies to take care of a dog if it is needed (snacks, poop bags, leash, blankets, first aid kit). I’m familiar with dog breeds & behavior & am aware of different training techniques so I’m not worried about being able to manage any dog- like getting them in their crate at the end of the night, or establishing a relationship with them, etc. I will care for your pet the way you want, but above all I will always care for an animal with the utmost respect & love, 💕

About: I’ve had cats and dogs in my life since I can remember. I have 5 cats (one senior) and I’m currently training my 6 month old puppy. I’ve watched my family’s pets several times without any issues. I’m working part time right now from home with flexible hours, so anytime you need me, I’ll be there for you and your fur baby. I treat any animal I take care of like my own making sure I go above and beyond for their care. They aren’t humans so we need to be extra sure they get what they deserve.

About: I don't have any pets myself, but I have lots of experience with them! I used to have chickens for several years, and I've also worked with horses as well. I gained a lot of experience working in a dog kennel, and became very comfortable with all different breeds and temperaments of both dogs and cats. I also have occasionally house sat for friends and family over the years and have taken care of several senior dogs. I love caring for animals and making sure they get the love and attention they deserve, so I can't wait to take care of your pet! I am now currently available at any time during the week except for early mornings on Wednesdays and Thursdays, and on Sunday mornings until 1pm. Currently I am not able to care for any pets in my own home, but I very flexible and can care for your animals however you wish in your home. I can easily adhere to any schedule you already have set in place for your pet, so any walks, potty breaks, or specific feeding schedules will be no problem for me.

About: I have had animals all my life, so I have plenty of experience. I currently have 7 cats, 3 dogs, 2 ferrets, & a horse making me well versed in the animal world! I currently work part time which will leave me plenty of time to be your pets new personal butler and snack dealer! I can’t wait to meet them! At my house my animals are the number one priority. Their needs before mine always! My cats never miss a meal, same as my other animals! My dogs go outside multiple times and I always make sure to include some play time in there as well!

About: Experienced with young fur babies, senior dogs, zoomies, and cuddle bugs. Excellent at sticking to a routine or just going with the flow! Here to provide ease to you and your fur family when you need a helping hand :) Currently living at home while finishing school, so my schedule is, as of now, pretty open (especially during the summer before school starts back up!). Try to be adaptable dependent on each pet’s personality. May or may not become a slight helicopter parent when providing care. Cute selfies of your fur baby will be taken and sent to you, so forewarning.

“I’m grateful to have returned home to happy and healthy cats, which I truly appreciate. It’s clear they were well cared for in my absence. That said, I did notice an excessive amount of food left in their trays, which suggests my written instructions may not have been entirely clear or closely followed. Next time, I would definitely provide a step-by-step walkthrough of their feeding routine to ensure everything is as straightforward as possible. Overall, I’m thankful for the peace of mind while I was away.”


About: I have pet sitted in my past and worked at grooming shops. Growing up, I've been surrounded by all types of animals, big and small, from birds to horses! Your pets will be safe with me! I have an open schedule to play with your pets! I am available any day of the week. I am very excited to meet you. When watching your pets I can be trusted to safely feed and water your pet! Your pets will also never get bored as I can also walk and play with them.

About: I’ve grown up with all sorts of dogs (energy & size wise) my entire life. I know how to deal with all different personalities. I also work full-time as a dog bather at a pretty popular dog grooming place around my area, so I have my fair share of dog experience! I am available for the given days on my profile- but can make accommodations given the circumstances. I currently work 9-4 on my available days at the dog groomer. I am always available to stop by and check in if needed. Although I do bartend/waitress most weekends- if need be- I can accommodate, though it is usually longer days and nights where I will not be available. We have a huge fenced in back-yard and a doggy camera (that also dispenses treats!) to check in when not home. Our golden now also loves car rides- so my car is set-up for a car ride if your dogs enjoys those.
Loving pet sitters in your neighborhood
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Brodi T.Star Sitter

“Above and beyond. Thats the service level I receive every time with Brodi. My Beagle Emma just adores attention and Brodi gives her lots of attention.”


Colleen Alisa B.

“Colleen is the best. We have used her numerous times and she always gives our kitty Max lots of love and attention, will definitely use her again.”


Marian C.Star Sitter

“You’re the best!! We can’t thank you enough for taking such great care of our puppy. It seems like he has so much fun with you. Love all of the photos you send. Thank you. So grateful we found you.”


Aria F.

“Aria was excellent, went above and beyond. Highly recommend!!”


Eileen R.Star Sitter

“Thank you sooo much! Vinny was well cared. Eileen sent photos and specific details about what Vinny did and the time frames she was with him. I'm so excited to know that Eileen is such a great pet sitter!”




Ashlin D.

“Able to come visit in very short notice. Very much appreciated. Took excellent care of our beloved doggo.”


Lacey S.
About: I have taken care of animals all my life in all stages of life. I very much enjoy playing and running around with dogs and cats Im a Stay at home mom and unemployed looking for work and a work out I love animals so I'm excited to start hanging out with all animals I have a well trained dog who is crate trained while I'm gone so ik how to use a crate properly. I love to play and cuddle with all animals can't wait to meet your fur baby


Kathryn B.Star Sitter
“Took great care of our dogs.”


Mercedes T.


“Mercedes is a very caring, thorough, and thoughtful caretaker, in addition to being a phenomenal photographer! I highly recommend and would happily use Mercedes again.”


Madelyne L.
“I’ve known Madi for 3 years now and by far, I can say that she has an unconditional love for animals of all sorts! She has cared for our dogs, our cat, our snake, our flock of 13 ducks, 4 chickens and 2 guard geese! When she comes over she greets and snuggles/holds all of them (the cat is not a snuggler and the snake is too small to snuggle still), all of their different schedules and needs are cared for; she is probably more attentive to all of them individually than I am! I highly recommend Madi to care for your pets! If she’s not familiar with how to care for them, she is a fast learner (our flocks are a good example). I have complete confidence that I can call and have no worries that my homestead is handled!”


Gia T.
“Gia is a very caring and compassionate person. She has always demonstrated a love for animals. She is also very organized and dependable as she has shown in taking care of many animals including dogs, cats and small animals. She would be a great caregiver for any pet.”


Sarah F.
About: I don't have any pets myself, but I have lots of experience with them! I used to have chickens for several years, and I've also worked with horses as well. I gained a lot of experience working in a dog kennel, and became very comfortable with all different breeds and temperaments of both dogs and cats. I also have occasionally house sat for friends and family over the years and have taken care of several senior dogs. I love caring for animals and making sure they get the love and attention they deserve, so I can't wait to take care of your pet! I am now currently available at any time during the week except for early mornings on Wednesdays and Thursdays, and on Sunday mornings until 1pm. Currently I am not able to care for any pets in my own home, but I very flexible and can care for your animals however you wish in your home. I can easily adhere to any schedule you already have set in place for your pet, so any walks, potty breaks, or specific feeding schedules will be no problem for me.


Madison W.
About: I have had animals all my life, so I have plenty of experience. I currently have 7 cats, 3 dogs, 2 ferrets, & a horse making me well versed in the animal world! I currently work part time which will leave me plenty of time to be your pets new personal butler and snack dealer! I can’t wait to meet them! At my house my animals are the number one priority. Their needs before mine always! My cats never miss a meal, same as my other animals! My dogs go outside multiple times and I always make sure to include some play time in there as well!


Kayla L.
About: Experienced with young fur babies, senior dogs, zoomies, and cuddle bugs. Excellent at sticking to a routine or just going with the flow! Here to provide ease to you and your fur family when you need a helping hand :) Currently living at home while finishing school, so my schedule is, as of now, pretty open (especially during the summer before school starts back up!). Try to be adaptable dependent on each pet’s personality. May or may not become a slight helicopter parent when providing care. Cute selfies of your fur baby will be taken and sent to you, so forewarning.


Kelly F.

“Kelly did a great job taking care of my cats. She was very reliable and had great communication. Would definitely recommend her to anyone looking for pet care.”




Jennifer P.

“Jennifer was AMAZING! She is generally quick to respond and extremely reliable. We felt confident our pup was well cared for when we left town. Thank you Jennifer!”


Tracey B.

“I’m grateful to have returned home to happy and healthy cats, which I truly appreciate. It’s clear they were well cared for in my absence. That said, I did notice an excessive amount of food left in their trays, which suggests my written instructions may not have been entirely clear or closely followed. Next time, I would definitely provide a step-by-step walkthrough of their feeding routine to ensure everything is as straightforward as possible. Overall, I’m thankful for the peace of mind while I was away.”


Leia D.

“Leia was wonderful to work with! I was able to go on my business trip without any worries.”


Bria B.
“Bria is a wonderful pet sitter. Whenever I am out of town she watches all my animals. She is very trust worthy! I'm glad I found her!!”


Chloe W.
About: I’ve grown up with all sorts of dogs (energy & size wise) my entire life. I know how to deal with all different personalities. I also work full-time as a dog bather at a pretty popular dog grooming place around my area, so I have my fair share of dog experience! I am available for the given days on my profile- but can make accommodations given the circumstances. I currently work 9-4 on my available days at the dog groomer. I am always available to stop by and check in if needed. Although I do bartend/waitress most weekends- if need be- I can accommodate, though it is usually longer days and nights where I will not be available. We have a huge fenced in back-yard and a doggy camera (that also dispenses treats!) to check in when not home. Our golden now also loves car rides- so my car is set-up for a car ride if your dogs enjoys those.
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!
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.
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 Village 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 226 pet sitters in Winchester Village. 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 Village pet sitters respond in under an hour.
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 Village.
Rover makes it easy to find Winchester Village 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 226 pet sitters in Winchester Village 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.
