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Top rated Winchester house sitters

“JaNiya is a phenomenal housesitter, especially if you have shy animals (but *any* animal would love her!). We have two skittish greyhounds and a very shy adopted cat. Within one day, our cat was sitting in JaNiya’s lap, and our dogs were relaxed and happy. I couldn’t believe it! She has such a calm, tender presence, and you can tell she adores animals. She’s even studying to be a veterinarian! Do not pass her up! She’s the only housesitter we’ll use from now on!”


“Oh my gosh being new to the area - I was so nervous about finding someone to trust with my fur babies who are seniors with different medicines and Trey was amazing. He diligently took care of all their needs, played with them, sent photos and videos , asked all the right questions...we are so thrilled to have him!!!”


“Della is a wonderful sitter, she made sure my puppy girls had fun walks and playtime and lots of snuggles. I was concerned my doggies would be stressed out in our absence, but Della made sure they were happy and comfortable, and sent lots of cute pics. Definitely recommend Della as a sitter for your furry family!”


“Kiara did such an amazing job watching my pup! My pup is reactive and nervous around strangers and she followed all of my instruction on how to interact with him and everything went great!”


About: Hi there! My name is Isabelle though i prefer to go by Astraeus. I’ve always been a part of pet-filled households. I even have my own pet! Even at a super young age neighbors would ask me to take care of their pets and they were always well taken care of. Your animal will be cared for and loved as if it were my own. I am currently working part-time, usually three days a week all on the same days. If anything comes up I’ll do my best to communicate thoroughly. I’ll do pretty much anything needed or asked of me for any pet. Just tell me and make it clear how and when i should do things.

About: I have had pets my whole life, I love every furry pet as if it was my own! I work during the day at home and I am able to be flexible around walking times and will be able to follow any instructions. I’ve managed giving pets medication if your pet needs any type of medicine when in my care I can assist! I will enjoy helping with your furry loved one! I have one small shih tzu named Oreo she loves playing with other dogs and going on walks. She is one year old and super friendly. I look forward to meeting each new fluffy face! Thank you and please let me know how I can assist your family and your fur babies! Feel free to ask any questions prior!

About: I currently work at Mann Veterinary Hospital in Owens Cross Roads, working towards my dream to become a vet tech and one day, a veterinarian! There, I work with dogs all day long! i can also walk your babies and give baths! I can’t wait to work with your fur babies! I typically work every other weekend, sometimes every two weekends, so message me beforehand! I get off at 5 everyday, and I’m off every Monday! I will never walk your dog without a leash. I will always make sure your pet has plenty of water and food when néeded! If needed, I can easily crate your dog!

“Mike is great with my dogs and an excellent communicator. He would frequently send me pictures and my dogs looked so happy. Left my house perfect. I could not recommend him more!”


About: My name is Shelby. I’m 23 and I have 2 dogs, a cat, a Bunny, Hamster and Two Turtles as my pets. I’m a Pet Groomer. I work at a pet daycare and boarding place. I love and respect animals. I am looking to gain more experience in pet care and I want to build by client base. I listen, take notes, and follow instructions. I will give your pet 100% of my attention while I am with them. I am excited to take on these new challenges in my life and look forward to taking care of your pet’s needs. Thank you and look forward to meeting you. Premium Bath Only! Bath, Blow dry, brush out, Scented spray , Nail trim, Ear cleaning, Fresh Breath treatment Small Dogs (Up to 15 Ibs) $30 Medium Dogs (16-40 Ibs) $34 Large Dogs (41-80 Ibs) $38 X-Large Dogs (81Ibs and Up) $42 Wash And Go Spa baths Bath & Towel dry Small Dogs (Up to 15 Ibs) $15 Medium Dogs (16-40 Ibs) $20 Large Dogs (41-80 Ibs) $25 X-Large Dogs (81Ibs and Up) $35 De-shedding Treatment Bath ,Blow dry, brush out, Scented spray , Nail trim, Ear cleaning. the prices are Small Dogs (Up to 15 Ibs) $20 Medium Dogs (16-40 Ibs) $30 Large Dogs (41-80 Ibs) $40 X-Large Dogs (81Ibs and Up) $50 Others spa services Ads ons Nail trim $12 Nail file $12 Nail trim & Nail file $18 Fresh breath treatment $12 Ear Cleaning $10 Paw Balm $8 Hypoallergenic Shampoo Upgraded $15 Flea and Tick Shampoo & Flea/Tick pet spray $18 Oatmeal Shampoo & conditioner Updated $11 Tea Tree & Aloe Shampoo & conditioner Updated $11 Nature's Miracle Skunk Odor Control Shampoo & Conditioner Lavender Scent Updated $11 Nail Polish $12 Hair color $20 add Glitter power $10 Pet Grooming service •Tidy up Bath & Trim Bath, Blow Dry, Brush out, Scented Spray, Nail Trim, Ear Cleaning, Basic Feet, Face and Sanitary Trim NO Body Take off!! Small Dogs (Up to 15lbs) $35 Medium Dogs (16-40 lbs) $55 Large Dogs (41-80 Ibs) $70 X-Large Dogs (81lbs and up) $90 • Full Groom Bath, Blow dry, Brush out, Scented Spray, Nail Trim, Ear Cleaning, Bandana, Bowtie or Hair Ties. Small Dogs (up to 15 lbs) $50 Medium Dogs (16- 40lbs) $60 Large Dogs (41-80 lbs) $75 X-Large (81lbs and up) $95 I will not be available those day on my calendar.My only day off is Sunday. let me know when it is best for your dog or cat to need a drop-in visit, dog walking, playtime and grooming. I have a private fence in yard, I also have crates if needed. I love spending time with dogs and cats as well as caring for them like family.

“I knew right away that we had found a competent, caring, and responsible dog/house sitter. Kristen proved to be exactly that. It’s such a relief to find someone like that. I will absolutely ask for her again.”


About: I’ve had cats almost my entire life, and small dogs for a few years as well, so I’m familiar with their personalities and needs. I treat every animal like they’re my own. I take time to learn each pet’s personality quirks, favorite toys, and cuddle preferences. I pay close attention to details, routines, and aim to make every visit feel like a mini vacation for your pet, and peace of mind for you! I go the extra mile to make sure your pet(s) feel safe, loved, and never alone. I send plenty of cute photo updates as well!! Pet care fits seamlessly into my weekly routine because I work part-time at home with a flexible schedule. I am a photographer as well, so I spend much of my day on my computer, which makes it easy for me to stay at your home and give your pets plenty of attention. I also co-parent three cats with my sister, so when I’m away, they’re well cared for, no worries there! They all have vastly different personalities, and dietary needs. This experience helps me understand the needs and comforts of pets in a busy but caring environment. I care for furbabies in my clients homes by following routines for feeding and providing fresh water, keeping the litter box clean, and offering playtime and cuddles. I offer gentle attention based on their personality, whether they want to play or just chill nearby. I keep an eye on their health and mood to ensure they stay happy and comfortable in their familiar space. I also send daily updates with photos or videos so you can see how your pet is doing. I’m experienced with cats of all personalities from shy, high energy, anxious, senior cats, to playful kittens. I’m also experienced with medication giving and different diets. Your pet’s comfort and routine are my top priority!

About: Howdy! My name is Pierce! I’ve been caring for pets of my own and of friends / family since I was 16! I’m available anytime of the day or night! I’ve taken care of rabbits, hamsters, turtles, tortoises, Great Danes / Pyrenees, Maine Coons, birds, nonvenomous / non-constricting snakes, rats and mice, and teeny fur babies alike! I can’t wait to meet your pets!! Just give me a holler! 😁 I have a redbone coonhound and an orange tabby of my own so I still care for animals every day, but growing up I lived on a farm with tons of animals! We had snakes and rats / mice as well! I’ve given shots to animals, and my old dog had to have arthritis medicine every day. I love every animal! I’m very knowledgeable with many different animals. I always let animals sniff me before I go in for a pet, and I’ve never met a pet that didn’t love me back!

About: I have been surrounded by pets my entire life, from dogs to cats to bunnies. With experience in overnight sitting and caring for senior dogs, I provide reliable and loving care. I'm comfortable administering medications and helping pets with special needs like diapers. Your furry friend will feel safe, loved, and cared for, just like family! I'm home for the summer and trying to work as much as possible. Currently, I have open availability to assist you and your fur babies! I provide personalized care by staying in your home, ensuring your pets feel comfortable and secure. Whether it's keeping them company overnight or taking them for walks, I prioritize their well-being and stick to your pet's routine. As a trustworthy and dependable person, you can feel confident that your home and pets are in safe hands. I’m committed to providing a safe, loving environment while you're away, so your pets get the attention and care they deserve.

About: I’ve always been around dogs my whole life. No matter what I’ve always put my pets first. They are truly my babies. And I’ll treat your fur baby like it’s my own. I can do weekly walks. Pet sitting. Im a really big animal person. And ill try my hardest to work around your busy schedule also!! My own puppies are always outside enjoying the nice weather. But they truly are cuddle bugs.im a huge outside person so many many walks to be enjoyed!!

About: I have been a veterinary technician for 3 years, and have experience working with and caring for dogs, cats, birds, fish, and rodents of all ages (a few days old-senior ages) for 10+ years. I currently work full-time at a veterinary clinic, but normally have 2-3 days off and often have scheduled half days where I am able to tend to my own pets as well as other people’s pets. I have a large yard and love walking, so your baby will get plenty of exercise. I also have cats and a dog, all of which are very friendly and well socialized, to keep your babies entertained and keep them company.

About: I have experience with dogs, cats, birds, horses. I have lived on a farm with chickens and everything above since I was one years old. I have an open schedule- happy to work with everyone’s pet needs in this busy life. Hoping to make your time away as stress free as possible. I am honored to be trusted with your beloved animals. I will care for them as if they are my own, truly! You won’t regret using me.

About: i've grown up always having a dog & i couldn't imagine it any other way. my dogs scarlett is my pride & joy & i can't wait to see all of your puppies ! i currently work 3 days a week so i have plenty of time to take care of your puppies ! It's also very easy for me to get off of work if im told enough in advance! I would love to be sent a text message or left a note , with detailed descriptions on how to take care of your pet the right way!

“Amanda was awesome to my little geriatric dogs. They are spoiled rotten and have several quirks to their care. She stayed a week in my home and very attentive to everything asked of her. Highly recommend!”


About: As a Rover Dog Caregiver, I am committed to providing exceptional care for your beloved pets. With a background in veterinary technology and a passion for animals, I ensure that your furry companions receive the attention, exercise, and affection they deserve. Whether it's daily walks, playtime, or overnight stays, I tailor my services to meet the unique needs of each dog, creating a safe and comfortable environment for them to thrive in. With me, you can rest assured that your dogs are in loving and capable hands. I often volunteer at dog sanctuaries with disabled and senior dogs. And I have one puppy and one adult (both female) of my very own!! I also have a female cat I adopted 5 years ago!! I’ve cared for various small animals and reptiles also. I am an upcoming freshman in a Veterinary Technology program. I’m currently working part-time and there is never “not enough time” to care for pets!! Everyday I take time out of my day from my dogs to enjoy my company. There is no excuse for neglect! Although I do not have a fenced home I have a LOT of yard space and my neighborhood is perfect for dog walks. I also live 5 minutes away from a trusted dog park. Just tell me what I can do to best care for YOUR animal since not all dogs/cats are the same.
Loving house sitters in your neighborhood
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JaNiya P.Star Sitter

“JaNiya is a phenomenal housesitter, especially if you have shy animals (but *any* animal would love her!). We have two skittish greyhounds and a very shy adopted cat. Within one day, our cat was sitting in JaNiya’s lap, and our dogs were relaxed and happy. I couldn’t believe it! She has such a calm, tender presence, and you can tell she adores animals. She’s even studying to be a veterinarian! Do not pass her up! She’s the only housesitter we’ll use from now on!”


Hugh "Trey" L.

“Oh my gosh being new to the area - I was so nervous about finding someone to trust with my fur babies who are seniors with different medicines and Trey was amazing. He diligently took care of all their needs, played with them, sent photos and videos , asked all the right questions...we are so thrilled to have him!!!”


Della B.

“Della is a wonderful sitter, she made sure my puppy girls had fun walks and playtime and lots of snuggles. I was concerned my doggies would be stressed out in our absence, but Della made sure they were happy and comfortable, and sent lots of cute pics. Definitely recommend Della as a sitter for your furry family!”


Kiara C.

“Kiara did such an amazing job watching my pup! My pup is reactive and nervous around strangers and she followed all of my instruction on how to interact with him and everything went great!”


Isabelle V.
“Astraeus has always been there for me in the past years as a great petsitter. My dog Bruno loves them and has been taken great care of by them. Always consistently checking, never left Bruno needing, was always clean. I trust them in my own house without me being there for prolonged times as well. I definitely recommend them as your next petsitter.”


Brigid T.

“Brigid was awesome! My pets lived her! She truly has a heart for animals and did great job home sitting! I will definitely be booking her again”


Taina P.
“Taina is a wonderful young lady who house sat and took care of our 3 dogs and 3 cats. She is attentive and responsible. The animals love her and so do we. Would highly recommend her as a dog walker.”


Brianna B.
About: I currently work at Mann Veterinary Hospital in Owens Cross Roads, working towards my dream to become a vet tech and one day, a veterinarian! There, I work with dogs all day long! i can also walk your babies and give baths! I can’t wait to work with your fur babies! I typically work every other weekend, sometimes every two weekends, so message me beforehand! I get off at 5 everyday, and I’m off every Monday! I will never walk your dog without a leash. I will always make sure your pet has plenty of water and food when néeded! If needed, I can easily crate your dog!


Mike M.

“Mike is great with my dogs and an excellent communicator. He would frequently send me pictures and my dogs looked so happy. Left my house perfect. I could not recommend him more!”


Shelby Sadler
“Shelby has helps me with my two dogs and four cats every week. If you are looking for somebody to care for your pets she’s definitely the person for you! My dogs and cats love her and always get excited when she comes over. You definitely will never be disappointed!”


Kristen T.

“I knew right away that we had found a competent, caring, and responsible dog/house sitter. Kristen proved to be exactly that. It’s such a relief to find someone like that. I will absolutely ask for her again.”


Tiffany S.
“I was a little nervous leaving my three dogs, especially my senior pup who needs extra care, but Tiffany turned out to be the best decision. She was incredible: patient, attentive, and truly loved animals. She gave my older dog the gentle care and attention she needs, while also keeping up with the energy of my two younger dogs (both 3 years old). I got regular updates and photos, which made me feel totally at ease. When I came home, all three dogs were happy, relaxed, and clearly well cared for. I’m so grateful to have had Tiffany care for my pups!”


Franklin T.
““Pierce is one of my three sons. He’s always had a natural way with animals and they always always love him. We had multiple dogs and cats while he was growing up. He cared for all kinds of animals: rabbits, hamsters, mice, birds, and turtles too! Whenever my husband and I are out of town he always watches over the house for us to make sure it’s not a complete wreck when we get back, and he’d send us pictures to keep us from missing our pets too too much while we’re gone. That’s really what made us think to tell him he should try to find a job pet sitting for people. He has a real knack for it!””


Alissa P.
“Alissa is one of the sweetest caregivers I’ve had for my Loki. She makes sure to get him well exercised with walks and playing fetch. She cares for him like he was her own. 10 outta 10 recommend.”


Courtney N.
“She’s great with Dogs she owns two pets and takes well care of and when she comes over to my house I have a smaller dog she always says hi too everytime and when she leaves you know she’s gonna say bye to my little dog named cookie . Everytime we are in public and theres a dog she gets so EXICITED!!!!!! Courtney is perfect for this role”


Kaitlyn P.
“I hired Kaitlyn to care for my elderly dog for a week while I had a family emergency out of state. Kaitlyn took Excellent care of Jazzy and always sent me a daily update/picture to ease my worries about being away from him. She was very responsible, she is dedicated and has a great passion for animals. Kaitlyn is friendly and dependable and I would hire her again in the future, if needed.”


Shaianne L.
About: I have experience with dogs, cats, birds, horses. I have lived on a farm with chickens and everything above since I was one years old. I have an open schedule- happy to work with everyone’s pet needs in this busy life. Hoping to make your time away as stress free as possible. I am honored to be trusted with your beloved animals. I will care for them as if they are my own, truly! You won’t regret using me.


jasmyne j.
About: i've grown up always having a dog & i couldn't imagine it any other way. my dogs scarlett is my pride & joy & i can't wait to see all of your puppies ! i currently work 3 days a week so i have plenty of time to take care of your puppies ! It's also very easy for me to get off of work if im told enough in advance! I would love to be sent a text message or left a note , with detailed descriptions on how to take care of your pet the right way!


Amanda B.

“Amanda was awesome to my little geriatric dogs. They are spoiled rotten and have several quirks to their care. She stayed a week in my home and very attentive to everything asked of her. Highly recommend!”


Laila R.
About: As a Rover Dog Caregiver, I am committed to providing exceptional care for your beloved pets. With a background in veterinary technology and a passion for animals, I ensure that your furry companions receive the attention, exercise, and affection they deserve. Whether it's daily walks, playtime, or overnight stays, I tailor my services to meet the unique needs of each dog, creating a safe and comfortable environment for them to thrive in. With me, you can rest assured that your dogs are in loving and capable hands. I often volunteer at dog sanctuaries with disabled and senior dogs. And I have one puppy and one adult (both female) of my very own!! I also have a female cat I adopted 5 years ago!! I’ve cared for various small animals and reptiles also. I am an upcoming freshman in a Veterinary Technology program. I’m currently working part-time and there is never “not enough time” to care for pets!! Everyday I take time out of my day from my dogs to enjoy my company. There is no excuse for neglect! Although I do not have a fenced home I have a LOT of yard space and my neighborhood is perfect for dog walks. I also live 5 minutes away from a trusted dog park. Just tell me what I can do to best care for YOUR animal since not all dogs/cats are the same.
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 on Rover as of Aug 2025 was about $40 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 36 house sitters in Winchester. 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, 86% of Winchester house sitters respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Winchester.
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 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.
