House Sitting Winchester
Find a loving house sitter to watch over your pets and your home.
Over 12 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.
“Hannah was great with our fur babies and they all loved her! She sent us pictures and videos throughout her stay which made us feel better about leaving them with someone new. She went above and beyond dealing with an accident with one of the pups on her first day and handled everything while we were gone. We recommend Hannah for pet sitting. She took wonderful care of our fur babies and treated our home with l respect. You can trust her with your furry family members.”
“Hey was amazing with our 3 dogs! Sent great pictures and even printed them out and left them for us. He comforted all our dogs during storms and even cleaned before leaving! Absolutely great!”
About: With two years at a dog shop, I've mastered boarding, grooming basics, and playtime. Growing up with dogs, now owning a Frenchton and Shih Tzu, I offer hands-on, loving care beyond the basics! I’m currently working part time at another job! So I’ll have plenty of time in the afternoons and weekends for all your fur babies needs! In my home and clients homes, I ensure pets have been feed, fresh water, and exercise. I maintain a clean environment, provide companionship, and follow specific care instructions from their owners.
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: Our home has always been filled with dogs and cats. The strays find me and know they will always have a spacial place to call their own. I own a small consulting business and have flexibility with my schedule. I am easing into early retirement and looking to share my love of animals. I am an experienced professional who is phasing into early retirement. I have spent years traveling and have an empathy for pet parents who have to leave their fur babies while away from home.
About: My name is Shelby. I’m 24 and I have 2 dogs, a cat and Two Turtles as my pets. I’m a Pet Groomer. I am full time work working with clients and taking care their pets while they are out of town dogs sitting and pet grooming/bath to make their furbabies them pretty. 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 Saturday and 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.
“Lauren was AMAZING!! One of my dogs can be a little timid with new people and she barked for maybe 10 seconds which was so insane to me. Her communication was amazing, the dogs absolutely loved her and she even made me ornaments with my pups paw prints on them!! 10/10 will be using her anytime my pups need a sitter!🤍”
About: I am friends and families go to dog sitter for when there is vacations, or someone is busy. I have been doing this for family and friends for a couple of years now im currently college student and would love to watch over your fur babies! with me being in school and work i’m normally pretty flexible with my schedule as all my classes are early in the morning! I have a huge fence around my yard and two adorable fur babies if yours are needing some company. I will be able to watch over your dog at all times if needed.
About: My name is Luke, I am a CATCH Canine Trainer Academy certified dog trainer. I use positive reinforcement to encourage and maintain behaviors. I have always had a passion for working with dogs but after losing one of my rescues to cancer only 2 months after saving her my passion grew. This had inspired me to help owners and their dogs learn and grow together. I am a Co owner of a food truck which we are only operating part time. On the opposite days I have open availability to help support you and your current fur baby. I am unable to offer boarding for animals at this time. I am certified in pet cpr and first aid through ProPetHero by Pro Trainings
“Mikki was the best! Our pets were well taken care of, our house was cleaner than we left it, and we received communication and updates daily. Absolutely would recommend and will book with again!”
About: I have many years of caring for pets and ran my own kennel in Florida for about 13 years and was a Vet technician for 8years I’m available weekends and can also be on call if needed. I can also be available on some Wednesday’s and holidays I’m open to any times I will care for your pet as if they are my own fur baby and will provide what is needed to take the best care of your pet
About: I have lifelong experience caring for pets, having grown up in a household with animals and being responsible for their daily care. I’ve also provided pet sitting services for friends, including feeding, walking, basic care, and ensuring pets stay comfortable and happy in their familiar environment. I am dependable, attentive, and committed to treating every pet as if they were my own I have a very flexible schedule and am available full-time for pet care. I currently do Walmart Spark deliveries, which allows me to create my own schedule and easily work around pet sitting, walks, drop-in visits, and other pet care needs. This flexibility helps me provide dependable care and plenty of attention for your pets I care for pets in their own home, where they feel most comfortable and secure. I follow your pet’s usual routine, including feeding schedules, walks, playtime, and any special instructions you provide. I also make sure they get plenty of love, attention, and companionship while you’re away. For dogs that enjoy getting out and about, I can take them on walks or trips to the park for exercise and fun. I treat every pet as if they were my own and strive to make their time away from you as stress-free as possible.
“Our giant doofus of a dog loved her. She took care of not only the dog and cat but also two dramatic pigs and two stubborn goats. When we had last-minute scheduling hiccups she was flexible and understanding. We're grateful we found her!”
About: I’ve taken care of pets from rabbits to dogs for several years. I understand that you know your pet best so I look forward to taking on the various tasks that your pet needs to continue to feel like you are the one taking care of them! My husband and I are run a commercial real estate company remotely. This puts us in the position to be flexible while pet and home sitting. We are active walkers and will gladly take your pet/s on a walk. I am attentive to their needs and I am able to follow special instructions. I love to take the customized approach since you know your pet best!
About: I’ve taken care of my pets for as long as I can remember. That moved onto actual sitting when I was in middle school. I have cared for elderly dogs, special needs animals, and puppies. I am reliable to take your overactive dog on the walk it needs and am comfortable with a multiple dog or mixed animal household. I am working part time in a pharmacy currently while I apply to pharmacy school. I have pretty flexible hours and am off most weekends! I have a small yard at my home and can easily crate your dog if needed. I live in a small safe neighborhood with many neighbors who also own pets.
About: I’ve had several different kinds of animals over my almost 30 years of life, and I consider myself a HUGE animal lover. I’ll take care of your babies as if they were my own… I’d own them all if I could! I work full time during the week, but I am available Friday-Sunday for boarding, or walks any time of the day! I’d love to get to know your fur babies! I have a fenced in backyard, with a doggy door to my back door- that can easily be closed off/shut. I have a spare bedroom so your baby could have its own room while visiting, or can easily spend the night in my room & share each other’s company!
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?
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
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 2 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 $55.5 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 67 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
Connect anywhere with the Rover app
