House Sitting in Winchester Estates
Find a loving house sitter to watch over your pets and your home.

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Top rated Winchester Estates house sitters

“Louise was amazing! She updated me along the way and took care of my dog while I was out of town! She responded quickly and made sure to send pics of my dog so I didn’t worry about her!! Highly highly recommend!!!!!”


About: I’ve had different types of dogs since I was young. I’ve trained dogs for all types of reasons. I’m a lover of all pups and can handle your dogs needs. I own a large property specifically for the environment, which is perfect for dogs. I look forward to meeting your doggie and returning a happy pup back to you. Please message for any details. I’m available on weekends and weeknights. I work full time M-F, so weekends are primarily open. While I can do many activities during the work week, I am gone about 8 hours for my primary job. Weeknights and weekends are available. I have a large property with plenty of room to roam. Chickens in the yard (in coop). I have a 6 year old pup of my own that is very docile, loves other animals and gets along with them easily, and is my number two. I don’t have a fence because my dog is perimeter trained. However, I can perimeter train your dog too or walk them on a leash if that is preferred. I plan to add a fence soon and will update this once I do.

“Michael was great with our dog and two cats while we were out of town. It was very clear to us that everyone was happy and well cared for. We also loved all the pics and updates. We highly recommend Michael and plan to continue using him to help take care of our crew in the future.”


“She was a wonderful animal sitter. She followed instructions and cuddled with the animals. There was daily updated and pictures send. She really did a great job or making the pets happy.”


About: I've had a cat and a dog for two years in Colombia. They're adorable, and I love spending time with them. I also take care of my neighbors' and friends' pets in my free time. On weekends I can take care of them all day or all night. On weekdays I can walk them in the afternoon from 6 pm to 9 pm I will take care of your pets, feed them and take them for walks. Any additional requirement, please let me know and we will do it.

“Kat took great care of our two dogs over a long weekend. One is an older Labrador, and Kat seemed to manage all the medications, frequent walks, assists up and down the stairs, etc. with composure and caring! The house looked great, and the dogs had obviously been well taken care of. I recommend Kat highly and without reservation!”


About: I have experience taking care of cats and dogs going back to my early teens. I’m just as much a cat lover as I am a dog lover and would love to take care of your fur babies. Whether you have a sweet big dog or a little shy cat, I love them all the same. Most of my family has at-least 2 or more cats or dogs and they often rely on me to take care of them when they go on vacation, have a long work week, or just need a helping hand. I currently work full time, 9-5 Monday through Friday. Most of my availability is on the weekends or late afternoons. But depending on the request I may be able to make an exception. I have experience caring for small dogs, big dogs, shy cats, energetic cats, senior dogs and cats. I’ve cared for almost every type of pet there is. I’ve even cared for reptiles and guinea pigs. Whether your pet would like space and quiet or someone to help them get their energy out I can provide that. I can meet the needs of your pet. Every dog/cat is different and I’m here for it all 😊

“Kacy was great with taking care of my dog, Luna! Luna is a very high energy, bully mix who can be a little crazy! Kacy handled her very well and Luna warmed up quickly to her, which was great because sometimes Luna can be wary of people. Definitely recommend Kacy!”


“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”


“Taylor is fantastic - patient with my grouchy old pup and kept up with my hyper young Aussie. An overnight trip was a stress-free experience for me and the dogs thanks to Taylor!”


“This was our first time with house sitting with Bo & she took excellent care of our pup & house. Daily updates with pictures is so much fun to have seeing how happy our pup was by staying in her own home. Thanks so much Bo! You will definitely be used again & again!”


“Always a pleasure to have Jason and Tracey sit with Little Buddy. They always treat him like one of their own! They go above and beyond and I never have to worry if things are going okay!”


About: I have taken care of many dogs from different families! As well as cats and other animals. I am able to give medication to them and meet all your needs. I will stay at your house and love to meet the animals before hand if you would like. I currently work a full time job at an elementary school, and part time at my church. When I Dogsit I normally stay the night or come over before work to take care of the animals . Then after work I am able to go and take care of them again. I’m very flexible for whatever your dog may need. I’m able to give medicine, walk the dog, create the dog, etc. whatever you need I can do!

“Anna was an amazing sitter to our two pups. My one pup is 14, has a lot of meds, and gets anxious when alone, so trusting someone to care for him is hard, but Anna surpassed our expectations. It’s such a relief to know I have a sitter I can trust to watch my dogs. She treats the pups like they are her own- I highly recommend!”


About: I've always been great with animals, able to read them and good at figuring out what they need. I volunteered at Animal Welfare League of Queen Anne's County for several years starting in High School. I've worked closely with large animals with behavioral problems, so I'm down the handle whatever quirks your pet has. My schedule is pretty open until the end of August when, I am starting my next semester at grad school. After that I have classes twoce a week but can still provide services with prior notice. I'm very adept at reading animals behavior and figuring out when they need attention, when they need space, and good at gaining an animals' trust.

About: I am very affectionate and will show attention to any animal. I have had 4 dogs and 3 cats, but now only have one dog and 2 cats, and love being surrounded by animals, they bring such happiness during my day! My mom has been a dog and animal all of her life and I take after her and show much concern and awareness for all animals. I love laying with animals, taking them outside and throwing them bones or toys, and of course a treat involved after! I am also very responsible at making sure ones anaimal is always stocked up on food and water and treats! I am looking forward into maybe working with animals as my career and this is one step closer!

About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.
Loving house sitters in your neighborhood
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Louise D.

“Louise was amazing! She updated me along the way and took care of my dog while I was out of town! She responded quickly and made sure to send pics of my dog so I didn’t worry about her!! Highly highly recommend!!!!!”


Seth G.
“I have known Seth for nearly 6 years and in that time I have seen what an incredible pet caregiver he is. He adores and takes such good care of his own dog, Ziggy (the sweetest boxer in the world), as well as a flock of lovely chickens who also adore him to the point of wanting to come into his house! I’ve seen him interact with and take amazing care of other animals too, including cats and ducks. Seth has such a warm personality and you can tell he truly cares for and loves animals. I would absolutely trust him to care for my own pets. He’ll go above and beyond to make sure your pet is cared for, not only covering the basics (feeding, watering, bathroom time, etc.), but also providing love, affection, and play. I highly recommend Seth to anyone looking for a pet sitter.”


Michael P.


“Michael was great with our dog and two cats while we were out of town. It was very clear to us that everyone was happy and well cared for. We also loved all the pics and updates. We highly recommend Michael and plan to continue using him to help take care of our crew in the future.”




Stacey B.

“Stacey is Amazing! Will definitely be using her in the future, she made our trip much more relaxing knowing our dogs were being taken great care of.”


Jordan D.

“She was a wonderful animal sitter. She followed instructions and cuddled with the animals. There was daily updated and pictures send. She really did a great job or making the pets happy.”


Laura C.
“Recommended! She is very careful with my pets and offers excellent service. We are happy with her work. Is Very responsive, friendly, and active person!”


Kat S.

“Kat took great care of our two dogs over a long weekend. One is an older Labrador, and Kat seemed to manage all the medications, frequent walks, assists up and down the stairs, etc. with composure and caring! The house looked great, and the dogs had obviously been well taken care of. I recommend Kat highly and without reservation!”


Alyssa B.

“Alyssa was great with our two beagles!”


Payton W.
“Payton is the best! If you are looking for someone who will go out of their way to make sure your pets needs are met and give you the comfort of great communication, she is your girl! She goes above and beyond putting herself in your shoes. She is easy to work with and very detail oriented, not to mention her great personality. She has taken care of all of my babies (3 cats and my new puppy).”


Kacy W.

“Kacy was great with taking care of my dog, Luna! Luna is a very high energy, bully mix who can be a little crazy! Kacy handled her very well and Luna warmed up quickly to her, which was great because sometimes Luna can be wary of people. Definitely recommend Kacy!”


Ashley C.

“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”


Cristina M.

“Kind, loving, responsible, and responsive care for our two pups (one who is a senior and needs extra TLC + daily meds). Highly recommend Cristina!”


Taylor M.Star Sitter

“Taylor is fantastic - patient with my grouchy old pup and kept up with my hyper young Aussie. An overnight trip was a stress-free experience for me and the dogs thanks to Taylor!”


Bohdanna G.


“This was our first time with house sitting with Bo & she took excellent care of our pup & house. Daily updates with pictures is so much fun to have seeing how happy our pup was by staying in her own home. Thanks so much Bo! You will definitely be used again & again!”


Jason & Tracy Y.


“Always a pleasure to have Jason and Tracey sit with Little Buddy. They always treat him like one of their own! They go above and beyond and I never have to worry if things are going okay!”


Julie K.
“Julie does an Amazing job caring for my pets during the day and sometimes overnights. She is so caring for them. Takes them for walks even at the beach. She is on time when it comes to meals. I have used her multiple tiles and will continue to use here.”


Anna H.

“Anna was an amazing sitter to our two pups. My one pup is 14, has a lot of meds, and gets anxious when alone, so trusting someone to care for him is hard, but Anna surpassed our expectations. It’s such a relief to know I have a sitter I can trust to watch my dogs. She treats the pups like they are her own- I highly recommend!”


Sean K.
About: I've always been great with animals, able to read them and good at figuring out what they need. I volunteered at Animal Welfare League of Queen Anne's County for several years starting in High School. I've worked closely with large animals with behavioral problems, so I'm down the handle whatever quirks your pet has. My schedule is pretty open until the end of August when, I am starting my next semester at grad school. After that I have classes twoce a week but can still provide services with prior notice. I'm very adept at reading animals behavior and figuring out when they need attention, when they need space, and good at gaining an animals' trust.


Sarah N.
“Sarah is a dependable, caring & trustworthy pet sitter. You can tell how much she loves all animals, esp cats and dogs. I would recommend her to anyone looking for a great pet sitter or dog walker.”


Aliciya M.
About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.
How Rover works
1. Search
Read verified reviews and choose a house 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 house and 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 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 Estates on Rover as of Aug 2025 was about $50 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 Aug 2025, there are 522 house sitters in Winchester Estates. 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, 89% of Winchester Estates house sitters respond in under an hour.
House sitters in Winchester Estates 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 Estates.
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 Estates 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.
