House Sitting Winchester
Find a loving house sitter to watch over your pets and your home.
Over 188 pet parents in Winchester have booked house sitting
Winchester, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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!”
“Kristine was very responsible taking care of our dog and home while we were gone for 4 days. In fact, more than we expected. We will definitely want her to take of Boots again when we need a dog sitter.”
“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.”
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.
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).
“Maya is amazing!!!! My dogs have never been left with anyone, so I was very nervous. She had so much patience with my babies! She sent me pictures and kept me updated. I highly recommend her, especially if you have never left your babies with anyone. She is such a wonderful!”
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: Hi, I’m Nina! My passion for animals started when I began volunteering at animal shelters when I was 13. By the time I was 19, I was working full-time at a doggy daycare where I learned puppy / senior care, light training experience, medication administration, exotic pet care, behavioral management, navigating social interactions / introductions, and much more in my 8 years there. I am currently working full time, Monday - Friday 8:30am-4:30pm but am hoping to change that soon to focus on my passion for animal care and socialization. I love hanging out and chilling with the dogs I meet and getting to know them. I will take your pets on walks, sit with them in the shade or outside, play with any toys they love, or just hang out on the couch if that’s their speed. My care is custom to your pet and their needs.
About: I’ve had both dogs and cats my entire life and genuinely love caring for animals of all ages and personalities. I’m experienced with feeding, walking, bathing, cleaning up after pets, administering lots of love and attention, and making sure they feel safe and comfortable while you’re away. I understand that every pet has their own routine, and I’m happy to follow any instructions to keep them happy and healthy. Whether your pet loves playtime, long walks, or just wants someone to cuddle with, I’ll care for them as if they were my own. I work Monday-Friday 8-5. I can take care of your pet(s) before and after work. On weekends I can spend even more time with your furry family!! I feel comfortable going to client’s houses to pet sit! I have pet sit for my aunt multiple times for her two pups— including a dog with a strict diet and medication for his seizures.
About: I have been around dogs majority of my life from puppy to senior. I have two dogs medium to larger dogs at home and have watched smaller dogs overtime. I am currently a college student athlete with free time during the day and night. I am very flexible with my schedule and pretty open on the weekends. I tend to be home from classes around 2-3:30pm. At home, my dogs are on shock collars because we have an open backyard that backs up to the woods. But I have also took care of several dogs that had fenced in backyards where they can freely roam.
“Julia is wonderful with our cat and taking care of our home while we are out of town. She kept us up-to-date throughout each day with photos and even a video of our little guy. She was very prompt and great at communication. Thank you so much, Julia!”
“Brenna was a wonderful pet sitter to our dog, Rocky over the weekend! She kept me up to date on how he was doing and sent me plenty of pictures and videos of him having a wonderful time! I knew Rocky was safe and being taken care of while in Brenna's care and I truly I appreciate that. Thanks again!!!”
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!
About: I love both cats and dogs and have had them my whole life! Today, I have a 4-year-old Shiba Inu that I rescued. I was given a Tuxedo cat for my fourth birthday and we got a Husky mix when I was around 10. I fed them and walked and played with them my whole childhood. When I was in college, I started fostering animals— both cats and dogs— for years on end. Some of the animals needed eye drops and oral medication which I helped administer. I even helped my mom adopt one of the cats I fostered! I promise to love and care for your pets as if they are my own! I work remotely from 2-10pm on Tuesdays-Saturdays! I’m best fit for mid-day, morning or late night walks and I am free for all-day/ overnight care on Sundays and Mondays. If I am able to work remotely from your house, I could also potentially work weekdays and weekday night. I can play with your pet and take your dog on long walks! I also have treats and toys at my disposal that I can share (per permission from the owner of course!)
“Kathy was an amazing dog sitter! We have 3 very large dogs - 2 Great Pyrenees and a Saint Bernard. She sent photos twice a day of each of the and gave us updates on how they were doing! She left the house cleaner than when we left & she was present in our home almost the entire time she was sitting for us. We will definitely be booking with Kathy again!! :)”
“Victoria stayed in our home to take care of our dog Mika. She was very conscientious and respectful of place and took great care of Mika. Victoria spent most of the day with Mika so she wasn’t alone. We returned to a very calm and relaxed pup. Victoria is a good communicator, anytime she had a question or concern she was quick to let me know. We won’t hesitate to use Victoria again.”
The median cost per night for house sitting in Winchester is $50
Pet parents share their Rover experiences - Winchester
Wow, where do I begin? Natalie took such good care of my Bailey and my home. I can’t say enough about how wonderful she was and how great the little “Bailey cheat sheet” she made that summarized all the care instructions I provided at our meet and greet, and the beautiful picture she took of Bailey while I was away. She’s thorough and attentive and sent great pictures and messages to reassure me Bailey was fine. And she was! Thank you, Natalie! You’re wonderful and I can’t wait to book you again!
Hailey did such a great job house sitting for us and watching our pups. She paid great attention to detail during the walkthrough and when meeting our pups and took notes to make sure she had everything for the weekend. We got lots of pictures and Hailey even took the time to bring our packages in. We definitely recommend Hailey and hope to work with her again in the future!
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!
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!
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!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
How Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 3 repeat house sitting clients
FAQs for House Sitting - Winchester
Frequently asked questions about Rover
The average cost for House Sitting in Winchester on Rover is $66.6 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of July 2026, there are 513 sitters on Rover offering House Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winchester walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winchester maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winchester choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winchester. On Rover:
- 97% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 95% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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