House Sitting Winchester Village
Find a loving house sitter to watch over your pets and your home.
Over 10 pet parents in Winchester Village have booked house sitting
Winchester Village, 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.
About: ⭐️ Meet and Greets with new clients ⭐️ DETAILED updates with photos/videos ⭐️ Extra Cuddles and Playtime ⭐️Seasoned in professional pet care Hi! I’m Savannah 🤍 your pet’s new favorite sitter (and probably their future bestie 🐾) I’m new to Rover, but I’ve always had a deep love for animals and truly enjoy being around them. At home, I have a sweet cat named Athena, and have always been raised around dogs so i definitely understand each one is different. I’m also a stay-at-home mama to my daughter—so I have a very flexible schedule and lots of time to give your pets the love and attention they deserve. I don’t just “check in” on pets—I take the time to learn their personality so they feel safe, comfortable, and truly cared for. Whether they’re playful, shy, or need extra patience, I meet them where they are, giving them love, attention, and playtime so they feel happy and at ease while you’re away 🤍
“Sarah was fantastic! I was very at ease that I had to be away for 9 days and know that my Griz was well cared for with her staying in my home. 10/10 recommend Sarah for your pet sitting needs!”
About: I've grown up with multiple dogs and pets my entire life, so caring for animals has always been a part of who I am. I got my own dog while I was in college two years ago, and she is truly my pride and joy. Being a pet owner has shown me how important it is to find someone you can trust to care for your furry family member. I treat every pet as if they were my own, making sure they feel safe, loved, and well cared for while you're away. Whether it's walks, playtime, feeding, cuddles, or sticking to their normal routine, I'm committed to giving your pet the attention and care they deserve. My goal is to give you peace of mind, knowing your baby is in good hands I recently graduated from college and completed a summer internship with JPMorgan, where I'll be returning full-time next summer. In the meantime, I'll be completing my MBA online, which gives me a very flexible schedule. Because my classes are online, I'm available throughout the day for walks, drop-in visits, playtime, and overnight care. I'm happy to work with your schedule and provide reliable, consistent care for your pet Your pet's safety, comfort, and happiness are always my top priorities. I understand how important it is to trust the person caring for your furry family member, and I'll treat them with the same love and attention I give my own dog. I'll follow your pet's routine, feeding schedule, exercise needs, and any special instructions to help them feel comfortable while you're away. I'll also keep you updated with messages and photos, so you can have peace of mind knowing your pet is in caring and dependable hands.
“Kaylee was an absolute BLESSING! Our dog is a rescue and a little shy and nervous of new people, situations. She did AMAZING with him. We had several bad storms during her stay and she sat with him and snuggled him to soothe him throughout. She was in tune to his emotions and absolutely put him first in every situation without hesitation! He was a very happy boy and we could NOT have asked for a better experience! She also took very good care of the house and communicated with pics and videos every day. She is THE BEST!!”
“Christine was great with our dog. She made sure to follow all of our instructions and attended a meet n great to meet us and our dog. She was always communicative and sent updates/pictures while we were away. We loved having her stay with our dog!”
“What a delight it was to have faith watch our four year-old golden retriever! It put me at ease knowing our Doggo was being well cared for. Faith did a wonderful job with communication starting from a meet and greet all the way to letting us know when she was leaving. She went above and beyond with check-ins and photos to washing and remaking the bedbefore she left. We will definitely be using Faith again for our future trips.”
“Dylan with the help of Sophie were so great with our dogs while we were away! They were exhausted when we got home so we know they played hard. We appreciate their help and the excellent care they provided for our boys.”
About: I have watched over many of my friends and families pets. The dogs I have watched in the past have been moderately large, and could be a bit wild at times but I was able to keep hold of the situation. I have also accompanied my family and friends when they had taken care of pets for other families. I had helped train a very wild pup for a friend, as well as a basic command which was sit. I absolutely love animals and even went to a program in high school for them. I am currently free during most times of the week. I am currently attending HCC, my classes being on Monday and Wednesday and do not stretch late into the day. I am very available to watch your pups or kitties! I can come during the mornings or evenings during the week depending on the day. I am also available to house sit. I care for them by learning their needs and wants first in their home. I understand every animal is unique and needs to be cared for in a way that works for them. I listen to the owner to ensure that everything will be safe and cared for in their absence.
About: I’ve have over six years of pet and house sitting experience. As a pet owner myself, I understand and provide the attention, responsibility, and kindness need to take care of animals. I have experience with working with animals who have anxiety snd other behavioral concerns should that be a need. I have flexibility in my schedule as I am a local college student. I am currently a part time employee but have plenty of time to attain to the needs or your pets! I am available for boarding weekends and weekdays as well as any other service you may need! I care for my pets with the utmost love, comfort, and kindness, in which I will also do with your four-legged friend! No matter the service, you pets will be in the great hands!
About: I’ve have always had a dog & cats since I was a child. I love all pet cuddles! And meeting new friends. I have one dog and two cats at the moment. I've dog sat for my friends and coworkers when they need someone to be with their babies for nights away or random drop ins to check on them. I'm looking for a fun way to make extra money and i couldn't think of anything better then spending time with dogs & cats while doing that. I work four days a week but it’s flexible! I’m available everyday after 2pm and if I have a good enough heads up I’m available 24/7 I can give you references of people I have house/pet sat for in the past. I’m comfortable crating your pet if needed. I’m easily available on my cell phone when I am pet sitting. And I can send updates whenever you would like.
“Trisha was AMAZING! She stayed for a week with my 14 y/o dog and two cats. She sent me updates with photos throughout the day, was able to give my dog his medicine and was so attentive with playing with them. I highly recommend and would absolutely book her again.”
About: I have taken care of dogs, my whole life whether they were my own or somebody else’s I absolutely love animals your animal will always be safe in my care and have the best time. I’m currently a stay at home mom so if I leave the house, I only leave to go to the grocery store or to grab the little one something to eat if they want it I have a huge backyard my house backs up against the woods. We are not close to the road at all. You’re dog would never be let outside alone my kids would run around in the backyard with them 💕
“Damien is SUCH a fabulous human. The extraordinary care he gave towards my fur babies warmed my heart. He went out of his way to text me pictures and updates on how things were going. I absolutely plan on hiring him again! Thanks! Sarah”
About: I’ve spent years caring for and training dogs, including raising and training four Australian Cattle Dogs—a breed known for its intelligence and high energy. Through that experience, I’ve learned how to read canine body language, reinforce good behaviors, and confidently handle dogs with different personalities and energy levels. I’ve also walked dogs for several of my mom’s clients throughout the Hockessin and Wilmington area. My focus is on providing safe, reliable, and personalized care while treating every dog as if they were my own. I’m currently home full-time, allowing me to provide attentive, personalized care throughout the day. Dogs in my care receive plenty of potty breaks, exercise, playtime, enrichment, affection, and supervision rather than being left alone for long periods. Your dog will be welcomed into a safe, loving home and treated like one of my own. I have a fully fenced 0.5-acre yard with plenty of room to run, play, and explore under supervision, as well as three friendly, well-socialized dogs for those who enjoy canine companionship. I also do my best to maintain each dog’s normal routine, including feeding schedules, medications, exercise, and any special instructions you provide. My goal is simple: for you to have peace of mind while you’re away and for your dog to feel safe, happy, and loved while they’re with me. I’m a Registered Nurse with a background in cardiac care and high-stress open-heart surgery, where being dependable, attentive, calm under pressure, and detail-oriented was essential every single day. After years of caring for my patients’ hearts, I’ve now been able to channel that same compassion into one of my greatest passions—dogs. I like to think I’ve gone from caring for my patients’ hearts to caring for my clients’ whole hearts—their dogs. ❤️🐾 My nursing background has shaped the way I care for animals. I take safety seriously, pay close attention to changes in behavior or well-being, follow instructions carefully, and understand the importance of medications and routines. Most importantly, I want owners to know they are leaving their dog with someone who is responsible, reliable, professional, and genuinely invested in their care.
“The most amazing experience with Elisa!! She was incredibly awesome with our very shy 2 dogs. She was extremely patient to gain their trust (not easy to do BTW lol) to the point that they even slept with her after getting to know her- that is how good she is! We loved Elisa and definitely will be our -go to- from now on every time we need a doggy sitter. Our girls got a new bestie with Elisa!”
About: I've taken care of dogs of every kind since my high school days. I love caring for and building relationships with dogs because they are truly like your best friend when they get to know and love you. Currently I work from home and for the most part make my own schedule every day. I am looking to build loving relationships with every pet that I care for so every owner can confidently put their trust in me to bring their furry friends back to me anytime they need me to take care of them. Me and my husband love dogs! We have a doggy park inside of our residence as well as a lovely community of people who walk their dogs everyday I’m sure your pet will meet some friends as we go out for walks and play at the park. Please let me know if you have any special food or any other request that you need me to accommodate to ensure that your furry baby is okay so I can be prepared as much as I can to welcome them into our home. I make my own schedule every day so i am pretty much free Monday through Sunday each week. I will make sure I update the time slots that are booked as clients start scheduling their appointments. All small and medium-sized dogs will be more than welcomed to roam freely around my living room kitchen area and are allowed to sit and lay on the couches as well. The floors are hardwood so even if they have an accident of pooping or peeing on the floor it will be alot easier for me to clean up on the hard floors than the carpeted areas. They will be allowed to come into my bedroom or any other room as long as I am in the room supervising them. I will take them outside to potty every 2 hours timed from the time they arrive until their scheduled time of leaving. You can feel free to bring their favorite toys they love to play with but I will also be purchasing brand new toys that I'm sure your dogs/cats will love to play with.
“Ann was fantastic staying in my home with my dog! I have an anxious pup and she did a meet and greet ahead of time to help him warm up. I knew she took good care of him with all her picture updates and I felt very comfortable knowing Oliver was in good hands. I wouldn’t hesitate to recommend her!”
The median cost per night for house sitting in Winchester Village is $50
Pet parents share their Rover experiences - Winchester Village
Sarah was absolutely wonderful and took amazing care of our dog while we were away on vacation. We really appreciated the photos and updates—it gave us so much peace of mind. This was our first time using a dog sitter, and it was comforting knowing our dog was in such caring and capable hands.
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.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for house sitting - Winchester Village
Select a filter and find qualifying sitters offering house sitting.Sitters in Winchester Village average 4 repeat house sitting clients
FAQs for House Sitting - Winchester Village
Frequently asked questions about Rover
The average cost for House Sitting in Winchester Village on Rover is $38.85 per night (as of August 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 August 2026, there are 1,187 sitters on Rover offering House Sitting across Winchester Village. 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 Village 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 Village 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 Village 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 Village. On Rover:
- 97% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 92% 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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