House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Was gone for about 3 days. Jessica was able to provide me with a morning and afternoon report on how my pets were doing and sent me plenty of pictures. I was so grateful and was able to enjoy my trip knowing that they were in good hands. My 2 cats and pup were so comfortable with her. Definitely recommend and will rebook again!”
About: I’ve had dogs my entire life, and got into dog training 2 years ago. I assisted a dog training company with the dogs they would board and care for, and assisted with multiple training outings. I also raised and trained my own service animal. I’m currently working part time, and will focus solely on providing care for your pet and home. They are my number one priority and love to do things with them. I will take them on long walks and do training with them to get their brain going. I’ll make sure their meals are extra tasty and made with love.
About: I have been a pet owner for as long as I can remember. I have had both dogs and cats and love them both equally. I have cared for pets for both family members and friends. I've watched all types of animals with many different personalities. On top of pet sitting, I have fostered multiple litters of kittens, which has taught me patience and attentiveness. In my free time, I also enjoy volunteering at a local rescue to help walk dogs. I understand the hard work, attention and love that goes into managing any kind of animal, and I am willing to do just about anything to make sure that your pet feels loved and safe. I am a grad student who only has in person classes on Tuesday typically 8am - 4pm, which makes me very flexible for the rest of the week. I am very conscious about safety when it comes to walk, and/or letting dogs out in a fenced in area. I am sure to read any instructions before hand to learn about any issues individual pet needs.
“Second time using Haley and she’s so great with my needy pup, Pax. She sent me pics every day, my house was left perfectly clean and she was extremely communicative. Will definitely book with her again!”
“Kathy G was awesome with our pups while we were gone. She sent updates, pictures and more every day which really kept us from worrying about our fur babies! She also left us a clean house and kept up on the dog items that needed washing. We will definitely call Kathy G again!”
“Linda was a life-saver and took such great care of our pets and house so we could attend to a last minute family emergency. She did a fantastic job and we will definitely use her again in the future.”
About: Animals have always been a huge part of my life. I currently have 4 cats and a 4-month-old puppy, so I understand the patience, attention, and love pets need every single day. Growing up surrounded by animals taught me how to care for pets with different personalities, energy levels, and needs. From playful puppies to independent cats, I’m comfortable handling feeding schedules, walks, playtime, cleanup, and giving pets lots of affection and attention. I treat every pet like family and always make sure they feel safe, loved, and comfortable while their owners are away. I currently work a flexible part-time job, which gives me plenty of time throughout the week to care for pets and give them the attention they deserve. Since I also have 4 cats and a 4-month-old puppy of my own, pet care is already a big part of my daily routine. Caring for animals comes naturally to me, and I enjoy spending my free time with them. I make sure every pet feels safe, comfortable, and cared for whether I’m in my home or a client’s home. I pay close attention to each pet’s personality and needs, whether they’re energetic, shy, young, or older. In a client’s home, I always follow instructions carefully to keep pets on their normal routine and help them feel as stress-free and comfortable as possible while their owner is away.
“Our 130# Newfoundland and cat were well taken care of. Communication was great, even using a different app since we were in Europe. Would not hesitate to use Charlotte again, she cared for our animals like they were hers.”
“Megan did outstanding her first time with Crosby and Luna! We were in contact daily and she made sure that everything went smoothly which is always a concern for me since Luna is a rescue still figuring things out. Communication leading up to the stay was above and beyond and my house was perfectly the way I left it and she even went the extra mile to wash and dry the towels and sheets. A girl after my own heart!!!! I would. highly recommend!!!!!”
“Shannon was great with our dog for a 2 night house sitting. She was excellent with communication and gave us updates and pictures while we were gone. She left our home in great condition, and we would definitely use her again!”
“Julia is wonderful with our cat! We always know he is in good hands. When we come home, it's like we never left. Julia always keeps us up to date with photos and videos which is really nice when we're missing him. Thanks so much!”
About: My family has had 2 dogs since I was 10 and two cats since I was 14 which I took part in caring for. Four years ago I also got a cat of my own! I have been fortunate enough to also care for pets from different friends and families while they’ve been away! So, I have a lot of experience feeding, playing, cleaning up after and caring for cats and dogs of all different breeds! I am currently taking some time off of work before starting PA school over the summer. So I have a pretty open schedule to figure out what works best for you and your furry friends! I am great at following any directions from you to ensure that your pet is safe with me! You let me know what standards and precautions you follow and prefer and I will always abide by them!
“Mary was so great with my three legged dog and my cat. She was communicating with me the entire time I was away, along with pictures and updates. I was able to enjoy my weekend because I wasn't worrying about my fur babies back home the entire time. Would recommend to a friend ✨️”
About: (Formerly Kamp Kelley) I have been fostering small dogs for a rescue group in No. VA. for the last 9 years (my aching back doesn’t allow me to work with dogs larger than 20 lbs)--prior to that I fostered cats and kittens. I has experience with many types of small dogs—especially Shih Tzu’s and Llasa Apso’s, but also Yorkshire Terriers, Basset Hounds, Pom's, Toy Poodles, etc. My expertise is in rescuing and caring for senior and special need dogs. Since I have a dog-friendly house and a large-fenced yard (1/4 acre) for them to run and play in, I decided to become a dog-sitter 5 years ago. I believe in loving and treating your fur-baby like my own! We keep her home and yard dog proof so your little angel will be in a safe, relaxed, dog-friendly, and loving environment! Because I am retired, my schedule is very flexible. I'm retired and except for occasional trips to the store, bi-weekly Bridge games. monthly book group and a occasional meeting, I'm home ALL THE TIME. At this point, I am accepting only ONE dog at a time EXCEPT if there are 2 dogs from the same household. Same for cats. I have a large, fenced yard that can be separated off. I have lots of dog equipment. For example large crates if your dog is used to being crated, bowls, beds and cushions, a big bed for them to share with me, jackets, leashes, kongs and lots of love and affection. Same for cats--EXCEPT, I let them out only on the back deck (enclosed).
“She was amazing! Came on time, follow all the instructions with my little puppy. Send me the updates and photos of Poet. Puppy was happy and safe when I came back home. Her prices are very affordable. You can feel that she loves the animals. Highly recommend Christopher!”
About: I have owned and trained dogs most of my life, grew up on a farm with all types of pets and find it second nature to treat them like family. I currently work from home and have a very flexible schedule. I can house sit, drop in or stay with your pet as long as you need someone. My dog has a fenced in yard and is at day care for socialization M-F so I can have my full attention on your dog. I currently work from home part time so I have plenty of time for your pet! I am awake early and have a flexible schedule to fit yours. I make sure you and your pet are comfortable with me and follow instruction when caring for your pet. You know your pet best and I want them to be happy and content with me.
Over 507 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
If you are looking for a pet sitter who will treat your fur baby like absolute royalty, look no further! We needed someone last-minute to watch our dog for an entire week, and she completely saved the day by stepping in with such short notice. From the moment we left, we were at total ease. She sent constant updates and a ton of amazing pictures throughout the week, which we absolutely loved. It was so reassuring to see our pup so happy, relaxed, and well-cared-for while we were away. She is professional, incredibly dependable, and clearly has a huge heart for animals. We are so incredibly grateful for her help and will absolutely be booking her again in the future. Highly, highly recommend!
Kristine is a warm and caring individual and my dogs picked up on that immediately. She was fantastic with our three German Shepherds. She took great care of our dogs and our home while we were away. She was respectful of our property, cleaned up after herself and the dogs, and went above and beyond by mopping up after a rainstorm and even throwing linens in the wash before we returned. It gave us so much peace of mind knowing everything was being handled so thoughtfully. Great communication, too. I would absolutely book Kristine again and highly recommend. Kristine, if you’re reading this, thank you so much for putting up with all the shedding, the Shepherds were dropping their coats like crazy.
Charlotte came for the day to get to know Finn, our little dog, before coming to stay over in a few weeks time. We left for the day and when we returned Finn was sitting next to her on the sofa looking content and happy:) Charlotte is a calm and friendly person who understands pups very well. :)
Could not be more pleased with the compassionate care our dogs received while we were out of the country on vacation! I am the animal worrier of the family and felt very much at ease while away. We returned to a home of happy puppies! Thank you so very much for providing top notch care!
Mary was outstanding! She pet and house sat for me while I was out of the country for 10 days. Coming home to a clean, maintained house and my happy pup made my trip a success! Mary has great communication skills, very thorough & understanding. She met and exceeded my expectations. Job well done and appreciated! Thank you, Mary!
She was amazing! Came on time, follow all the instructions with my little puppy. Send me the updates and photos of Poet. Puppy was happy and safe when I came back home. Her prices are very affordable. You can feel that she loves the animals. Highly recommend Christopher!
Kathy G was awesome with our pups while we were gone. She sent updates, pictures and more every day which really kept us from worrying about our fur babies! She also left us a clean house and kept up on the dog items that needed washing. We will definitely call Kathy G again!
What an absolute Doll Tearia is… she did a fantastic job with our babies today… she put the thunder hood and thunder shirt on one of my Goldens during the storm. She was on time and the house was perfect when we got home. She left a lovely note and we will definitely be calling her in the future! Top notch!
Kim is an incredible human, and our first choice with who we will trust with our home and our pets while we are away. She is excellent at giving updates and sending pictures, she is on time, she is kind, trustworthy, and she clearly loves her work. Thank you, Kim!
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. 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 away
3. 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 house sitting in Winchester is $50
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.
Sitters in Winchester average 3 repeat house sitting clients
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 Jun 2026 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 Jun 2026, there are 303 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.
House sitters in Winchester have an average of 14 years of experience. House sitters with repeat customers have an average of 3 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.
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.
Connect anywhere with the Rover app
