House Sitting Winchester
Find a loving dog sitter to watch your dog overnight in your home.

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.
“Carson did a wonderful job house sitting with our German Shepherd for 1 week. She sent pictures and updates. We were quite comfortable leaving our boy, Jax, in her care. I would not hesitate using Carson again in the future.”

“Adam and Chelsea provided excellent care to my three dogs! They kept my house clean! I can’t give them any more than five stars, but I would give them 10 if I could. Hopefully I can be a repeat customer if the dogs didn’t scare them off too bad. Adam and Chelsea, thank you for making me feel comfortable that my dogs were in wonderful hands! You guys are the best!!!”

About: Nice to meet you, I'm Kat! I have been working in the pet industry since early 2019 - beginning as a kennel attendant, evolving into a professional dog trainer in two prominent KC training facilities, and now running my own small business. I am thoroughly versed in canine care and communication, and use my expertise to help every dog I care for have a comfortable and positive experience. Not only that, but I am also very knowledgeable in canine enrichment and stimulation. Have a high-energy, high-needs breed? They'll end their days with me happy and tired. A senior dog that has special needs and benefits from therapeutic stretches? Say no more. Puppies are absolutely welcome as well, and I would love to provide them with opportunities to practice socialization, confidence building, and manners. My experience also means that I am able to care for dogs with behavioural issues and special health needs. I know it can be difficult to find care for dogs with "quirks," and I hope to make that search a little easier. Send me a message and we can chat about your dog and if I would be a good fit. I'm looking forward to meeting your pup! ** I do have a part-time job that takes up much of my time on Fridays, Saturdays, and Sundays. This doesn't mean that I'm totally unavailable those days, but we'll need to chat to make sure that my schedule works for your pet. 🙂 The pets I work with are my priority! I want to make sure that my schedule allows me to look after your furry family members' needs. I do work long hours on weekends - but sometimes this can be flexible. We'll have a thorough chat before you book to make sure that your pets will get all of the attention they need and the love they deserve. 🐾IN MY HOME (boarding):🐾 (See "IN YOUR HOME" section below for housesitting. Boarding is dogs only. If you have other kinds of pets, please choose housesitting. Thank you!) My house is pretty well "dog-proofed" and oriented in a way that I am able to keep a close eye on pets from just about anywhere! So your pup gets to be the king of the castle, with lots of room inside & outside to run and play. Not to mention the mountain of toys.... When I cannot monitor them, they'll get to chill in a cozy crate or pen, with fresh water always available and a chew toy, puzzle, or snack to keep them entertained. For walks and other adventures, I will always keep your dog leashed and close to me. I love to take dogs out on excursions to parks, trails, and other such places! Of course, I will always check with you first to make sure that we don't go somewhere your dog doesn't enjoy. I have three adult dogs (all ~45lbs) and a cat in my home. The cat is dog-friendly, but also is able to be kept entirely separate from your dog if needed. My dogs are all 100% dog-friendly, have good play manners, and are also able to be neutral around/ignore other dogs when told. They are very patient with young puppies as well! And if your pup isn't one for new friends, don't worry - they can be kept totally separate on request, and your dog will still get plenty of one-on-one playtime & snuggles with me. It is 100% up to you if your pup has any interaction with other dogs (or the cat). Full separation is possible, but if you'd like your dog to make some furry friends, I am happy to safely facilitate that! All interactions between your dog and other pets will be of limited time and monitored - the dogs will never be alone together. For safety and management reasons, I cannot accept boarding bookings for dogs that are not able to be comfortable in a crate (or pen, for small dogs only). Have other questions or concerns? Send me a message and let's chat about it! Updates will be sent daily, as well as pictures and videos. I look forward to meeting your furry friends. 🐾IN YOUR HOME (housesitting):🐾 Dogs, cats, and exotic pets 👍 (See "IN MY HOME section above for boarding.) Your house, your rules! Before the booking, you & I will have a detailed conversation about your pets' schedule, rules, needs, and preferences. I am happy to follow all of that to a T! My job is to keep your pets happy and safe while you are away. With 7 years of pet care experience, I am confident in caring for all of their needs. This includes pets with behavioral concerns and special needs! For walks and other adventures, I will always keep your dog leashed and close to me. I love to take dogs out on excursions to parks, trails, and other such places, but I will always check with you first to make sure that we don't go somewhere your dog doesn't enjoy. Updates will be sent daily, as well as pictures and videos. I look forward to meeting your furry friends. (Scaled or feathered friends welcome, too!)
About: I've had a dog since I was 10 years old and caring for him has been a big part of my life. I started dog sitting last summer and quickly realized how much I loved it! I genuinely enjoy spending time with dogs, whether we're going on walks, playing, or just relaxing. I treat every dog like my own and I make it a priority of mine to do my best to keep them in their same routine so they can be as comfortable as possible while you're away. I'll make sure your pup gets plenty of exercise and love! I'll also be sure to send plenty of photo and message updates so you know your pups are in good hands! I'm going to be attending University of Kansas this fall and my schedule is very flexible. I will only have one class Monday, Wednesday, and Friday which gives plenty of time to provide attentive care throughout the day. My weekends will also be open, making it easy to accommodate weekend bookings. I will care for your pets in their home by keeping their routine as close to normal as possible. I'll stick to your instructions about feeding, walks, potty breaks, medication, or any other special care they may need. I want your pups to feel safe and comfortable while you are away. I will send regular photos and updates so you can be at ease knowing your fur baby is in good hands.
About: I’ve had a dog for most of my life, starting as a kid when I begged my family to have one. I’m looking forward to having the opportunity to care for your dog. I work full time at an elementary school. I’m not able to let your pets out on my lunch break but am available outside of the times I’m at work, which is usually Monday-Friday 8am-4pm. I consider dogs to be members of the family. When I have had my own dog in the past, they were generally rarely alone, always going to work with me and on errands.
“Leo took great care of our dog and our house. He sent photos to us everyday, and our dog so looked so happy I thought the pup wouldn't want us to return home. Leo was good with communication. It is obvious Leo loves dogs. I would highly recommend him!”

About: I was always around a dog as a child and grew up knowing what they wanted, when to go outside, when to feed them and make sure they were played with. They can be unbelievable friends and I think they keep our lives actively expanding. I like to work part time and do the dog sitting when ever it's needed. It can be a random cases and I'm more welcoming to act on immediate services needed. I male sure the pet doesn't get into anything. For example: The trash can, anything chemical on the floor and make sure before they come over...if dog is being watched from my home. I make sure to clean up vacuum and make sure it's an very clean environment. Only feed them what pet owners advise me to give their dogs.
About: My sister runs kennels of all types of animals, i’ve gained so many experiences from her to bring proper care to your (fur) children ! i currently work part time as a barista, and i love animals so much so why not fit them into all of my free time! i have a big fenced yard that we keep clean, i have big pet beds and 3 different watering stations at my house. I am very good at reading animal language and have a certain knack for taking care of animals!

About: I have extensive experience caring for animals, as I’ve had pets in my home since I was a baby. Growing up around pets taught me responsibility at a young age, including feeding, grooming, cleaning, and making sure animals feel safe and comfortable. Over the years, I’ve cared for a variety of pets and have become very attentive to their needs, behaviors, and routines. I understand how important it is to provide not just basic care, but also companionship, patience, and love. My lifelong experience has made me confident in handling different personalities and ensuring pets are well cared for while their owners are away. I am a full time college student and work a part time job as a server. Most of my availability is in the mornings on weekdays and weekends as needed. I am a reliable and caring pet sitter with extensive experience providing private pet care for families. Over time, I’ve built trust with pet owners by consistently showing up on time, following specific care instructions, and treating every pet as if they were my own. I’ve cared for pets with different routines, temperaments, and needs, which has made me adaptable and attentive in any situation. Whether it’s feeding, walking, administering basic care, or simply spending quality time with pets, I always prioritize their comfort, safety, and happiness while their owners are away.
“Lilia was amazing with our rescue pup, Berkley! She is super calm and kind - we could tell our Berkley already felt comfortable around her the first time she met her! She sent us many photos throughout the weekend. She was very communicative and professional. We would recommend her to any friend or family member!”

About: I understand that your pets are family. My goal is to provide dependable, compassionate care so you can have peace of mind while you’re away. I offer pet sitting, house sitting, dog walking, drop-in visits, feeding, fresh water, litter box cleaning, waste cleanup, playtime, companionship, medication administration (if needed), and lots of love and attention tailored to your pet’s routine. Whether you have energetic dogs, independent cats, or multiple pets, I’m committed to making them feel safe, comfortable, and cared for in their own home. I’m reliable, trustworthy, and treat every home with the same respect I would my own. I believe in clear communication and will gladly provide updates and photos so you can see how your pets are doing while you’re away. Because I am a full-time online student, my schedule is incredibly flexible, allowing me to make pet sitting my top priority. Unlike a traditional 9-to-5 job where I would be away from the house all day, my school structure allows me to work entirely from home on my own terms. This means I have ample open blocks of time throughout the day dedicated solely to pet care. I can easily accommodate structured feeding times, frequent potty breaks, and mid-day play sessions without interruption. Your pets will receive consistent companionship, and because I'm studying from my laptop, I am available to provide the constant supervision, love, and attention they deserve." When caring for pets in your home, my primary goal is to maintain their regular routine so they feel safe and secure while you are away. Seamless Routine Adherence: I strictly follow your established feeding schedules, medication timelines, and specific instructions to keep their environment predictable and stress-free. Meticulous Cat Care: As a multi-cat owner myself, I know the importance of a clean environment. I scoop litter boxes thoroughly during every visit and sweep up any tracked litter. Quality Companionship: Because my full-time student schedule is so flexible, I don't just rush in and out. I dedicate genuine time to interactive playtime with their favorite toys, gentle grooming, or just quiet companionship on the couch while I study. Home Respect & Communication: I respect your space, leave it exactly as I found it, and provide you with detailed daily updates and plenty of photos so you never have to wonder how they are doing.

About: I’ve always taken care of my family dogs growing up and walked neighbor dogs when needed. Have enjoyed cats in my life as an adult I’m retired and look forward to caring for animals as my second act. I love seeing happy parents and pets when they come together again. I would love to get to know you so I can learn your pet needs and loves, if cuddles or being independent. Give me a call!
“Emily watched our babies for a week and I think they were sad to see her go! She did an amazing job - even our kitty who likes no one but us loved her! She went above and beyond in my opinion!!”
About: I always insure that pets are comfortable! I’ve taken care of old cats and dogs, and I when they are old like that it’s important to meet their needs first, as most of the time they need a lot of guidance and help. I am currently going into online college, so most of my day is free! I often sit down and watch TV or play video games, but I mostly enjoy writing and drawing in my free time I personally like to ask owners how there pets are in the company of others, as well as if any weather bugs them! The comfort of my pets, and owners is always my number 1 priority! I want to make sure that they are comfortable around me, and I never approach any animal until I’ve let them sniff me, it’s important that they trust me to be around them.
About: I’ve been around animals my entire life and currently share my home with two dogs and two cats who are truly part of the family. I have years of experience caring for friends’ and family members’ pets and homes, and I love making every animal feel safe, loved, and comfortable while their humans are away. Whether they’re snuggling on the couch or playing outside, I’m happiest when animals feel like their owners never left! I’m available at all times, and caring for your pets and home is my top priority. I never rush time with them — I make sure they get the attention, routine, and gentle care they need to feel safe and relaxed. Your animals will be treated with patience, love, and the same dedication I give my own. I treat every home with the same care and respect as my own. You can trust that your space will be kept clean, safe, and exactly as you left it. My priority is making sure your pets feel secure, loved, and completely at home while you’re away. Their safety, routine, and comfort always come first.
About: I have a lot of hands on experience with a variety of breeds and temperaments from my family and various jobs. Every dog is different and deserves to be treated as so with a great amount of patience and care. I have had hands of experience with ptsd/reactivity even though every situation is different and learning more every day. I’ve had a lot of time spent with senior animals who require more patience and attention in their day to day care. I do work a full time job but have a flexible schedule for mornings, evenings, and nights. I can have a very structured schedule so fitting any form of pet care will be a quick and easy adjustment. I follow any instructions or tips regarding your pet. Not only does it keep your fur baby safe, but gives safety for me as well. Leaving your pet is not easy, so it is extremely important for me to do to my absolute best to adjust to your already set routine you have in place.
The median cost per night for house sitting in Winchester is $40
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?
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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.
Meet local sitters who will treat your pets like family

1. Search
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Popular requests for house sitting - Winchester
Select a filter and find qualifying sitters offering house sitting.Sitters in Winchester average 3 repeat house sitting clients
FAQs for House Sitting - Winchester
Frequently asked questions about Rover
As of October 2026, there are 330 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.
<b>Tip:</b> 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
sitters on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winchester. On Rover:
- 96% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 96% 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.





