House Sitting Winchester

Find a loving house sitter to watch over your pets and your home.

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Over 159
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.

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Sitter Profile Image: Julianna O.
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Julianna O.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 60 reviews
26 repeat clients
20 years of experience
Winchester, VA, 22601

“Julianna is the best! She did a great job taking care of our kitten. She regularly sent us updates and even a video! She took very good care of our home while we were away. We appreciate having such a wonderful caregiver for our kitten.”

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Kristyn A.
Sitter Profile Image: Kathy G.
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Kathy G.
from
$75
per night
5.0 out of 5 stars
• 59 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

“Kathy watched our dog and housesat for us for an entire week. She communicated with us the entire time and sent photos and videos. She kept the house spotless and made sure to bring in the mail every day. We were never worried about our puppy or the house. Kathy was great and we can’t wait to book her again.”

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Jessica M.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$35
per night
4.5 out of 5 stars
• 8 reviews
1 repeat client
23 years of experience
Winchester, VA, 22602

“Victoria provided frequent comms and was very responsive. Great job, we will definitely use her again!”

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Stu Y.
Sitter Profile Image: Linda S.
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Linda S.
from
$75
per night
4.9 out of 5 stars
• 104 reviews
53 repeat clients
40 years of experience
Clear Brook, VA, 22624

“Linda was a great find for us. We moved back to the area about a year ago and needed someone to stay with our “kids”. We’ve used Rover in the past so we turned to them again. After a lot of searching for someone that could take care of our elder pups needs we landed on Linda. It was short notice for her (I procrastinated) but she made it work. Linda stopped by the house for a visit with everyone and the kids approved. We were very pleased with Linda’s approach and style. She took care of our home and babies like they were her own. We highly recommend Linda. She’s a keeper. We will be booking her again.”

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Phil C.
Sitter Profile Image: Paloma A.
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Paloma A.
from
$45
per night
1 year of experience
Stephenson, VA, 22656

About: Hi! Paloma** 🐾 I’ve had dogs for year, three, in fact, over the course of my life. I recently said goodbye to my last pup, and while I’m not ready for a full time dog in my home just yet, I miss it all deeply: the walks, the game of fetch, the pure joy and love only a dog can give. I am not new to dog care, I’ve looked after many dogs over the years, but this is my first time doing it through Rover! I’d love the chance to give your pup some of that same love and attention while you enjoy a vacation, work trip or time away. I treat every dog like my own, patient, attentive, and always up for a good walk or a solid game of fetch. Looking forward to meeting you and your pup! I work 9-6 hybrid, Monday thru Friday with somedays being fully remote. I am home most weekends and spend my free time walking, doing arts and crafts or gardening. Peace of mind is definitely important when it comes to my fur babies, I know that first hand. I can send check in photos with every walk, treat and meal if that is what you wish. I like to also take them to the dog park in my neighborhood if they play well with others. 3 walks a day minimum will be provided unless more are required. I currently working on building a fence to m a backyard and should be completed but end of September!

Sitter Profile Image: Marian K.
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Marian K.
from
$35
per night
10 years of experience
Winchester, VA, 22601

About: I have been taking care of dogs and cats since high school! I am comfortable and familiar with multiple pets at once and even some more eclectic animals like reptiles (turtles and snakes). I would only be able to come to your house to pet sit or walk, I would not be able to bring pets to my apt. I would only be able to pet sit in your home as I live in an apartment where I am unable to bring animals into my space.

Sitter Profile Image: Sherry R.
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Sherry R.
from
$63
per night
5.0 out of 5 stars
• 25 reviews
8 repeat clients
3 years of experience
Stephens City, VA, 22655

“She is awesome. Did a great job, knowledgeable, very nice. Will definitely use again sometime.”

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Elliot A.
Sitter Profile Image: Jose O.
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Jose O.
from
$80
per night
6 years of experience
Winchester, VA, 22602

About: Hi my name is Jose Alfredo and I can be very laid back and socially outgoing with a fun and friendly personality! I love being around friendly pets and I was a previous cat owner for 4 years. I also used to share my place with my close friend and his dog of 3 years who I helped care for many times. I have other family members and friends who have pets as well and I have been around them long enough to love and know me. I have spent a lot of time around other people's dogs most of my life and have great experience with both dogs and cats. Being around other people's pets over time has given me the opportunity to know and understand different dog and cat personalities and each ones individually unique needs and traits. Book me and I will walk your dog, feed it, play with it and make sure it has gone to the bathroom. I will tend to your cats' need as well and make sure it's fed, hydrated and help maintain it's litterbox's cleaniliness and given lots of attention! I am also willing to help with small house chores like taking out the trash, bringing the bin to the front, watering your plants or any other simple house duties for no extra charge! At the moment I will go to you to take care of your pet in your home so you don't have to worry about putting your pet in a new environment it's not used to. I will make sure everything in your home is as tidy as before I even arrived. As long as you can provide me with the proper details and instructions about your pets' needs, where things are and how to get in and out of the house, then I promise you everything will be done as requested. As a way of building trust, we will arrange to do a proper meet and greet at your home or a public place like the park. This is so me and your pet can get familiar with each other, earn trust between owner and sitter, and have comfortability and assurance that your pet and home will be in good hands. Thank you for choosing me to care for your pets! I am currently flexible with availability for most days of the week as I do not have any other full time job at the moment. However, I currently am a student studying full-time and sometimes get involved in campus events, extracurriculars, and other student organizations. So Tuesdays and Thursdays I'm typically more busy with classes. But as long as the requested time works around my schedule and classes then we can make it work and I can be available whenever I am not spending time on campus. I do prefer to be notified at least 3 days in advance for requests but I am also willing to take up to same day bookings as long as I am completely free for that day, but it is not guaranteed. But please do try to reach out and book with me in advance at first if possible. I also prefer to schedule a meet and greet prior to accepting booking requests for new first time clients. But I will be more than happy to work with you so I can make a new furry friend if we are a great fit for each other! I used to play with my roommate's dog every day and feed him or take him outside to potty when the roommate was not around or unable to. I play ball with his dog, tug of war and give him belly rubs. His dog is also very attached to me as I am to him. I also was a cat owner for 4 years who I took care of every day from feeding him to ckesning his litterbox and playing with him. I hope to form this same kind of relationship with your pet!

Sitter Profile Image: Stefany P.
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Stefany P.
from
$60
per night
3.7 out of 5 stars
• 3 reviews
5 years of experience
Winchester, VA, 22602

About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)

Sitter Profile Image: Liza E.
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Liza E.
from
$50
per night
5.0 out of 5 stars
• 1 review
15 years of experience
Winchester, VA, 22601

“Liza was AMAZING! My prearrange Sitter canceled three hours before I had to leave for a Fourth of July party and Liza was ready to go and eager to help! I am so thankful and grateful! What absolutely be using Liza again!”

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LN C.
Sitter Profile Image: Mark R.
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Mark R.
from
$50
per night
5.0 out of 5 stars
• 5 reviews
35 years of experience
Winchester, VA, 22601

About: I've been around dogs and cats since an early age, and quickly establish rapport with them. I've always taken good care of my pets, and will take good care of yours. I specialize in hour-long visits, giving your dog time to exercise and relax. I can take them to parks and give them an emotional lift for the day. I will treat them like my own pets. I work remotely, and can fit pet care in when needed. I live near Old Town and can quickly reach properties in the surrounding area. Caring for an animal goes beyond filling a bowl or taking a walk. That's why I enjoy building rapport with animals, so they feel happy and safe.

Sitter Profile Image: Ruby K.
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Ruby K.
from
$40
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
Winchester, VA, 22602

“Ruby was excellent. She was flexible and responsible. She followed instructions and kept us updated. Thank you Ruby!”

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Angela E.
Sitter Profile Image: Hannah L.
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Hannah L.
from
$40
per night
3 years of experience
winchester, VA, 22602

About: I have been dog sitting/ walking for several years. The most dogs I have handled at 1 time was 3. I own 2 small dogs myself how ever I have experience handling big dogs as well. I have experience administering medication. I work 4 days on 3 days off so I would love to provide care for your animals on the days I have off! I'm more than happy to help! I can take your dog on daily walks, I love hiking can take a well trained dog with me! i trained my own to go with me, they're great both on and off the leash. I love any and all dogs and would love to give yours pets and attention.

Sitter Profile Image: Elizabeth R.
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Elizabeth R.
from
$160
per night
5.0 out of 5 stars
• 7 reviews
3 years of experience
Stephenson, VA, 22656

“I can’t say enough great things about Elizabeth! From start to finish, she provided exceptional care for my dog, treating them like family. She was attentive, reliable, and went above and beyond to ensure my pup was happy, safe, and well-loved. Communication was excellent—I received regular updates, photos, and videos, which gave me peace of mind while I was away. It was clear that Elizabeth truly cares about animals and understands their unique needs. My dog came back happy, relaxed, and well-exercised, which is the best sign of a fantastic sitter! If you’re looking for a responsible, trustworthy, and loving person to care for your pet, look no further. I will definitely be booking with Elizabeth again in the future!”

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leonard A.
Sitter Profile Image: Zeel L.
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Zeel L.
from
$60
per night
4.9 out of 5 stars
• 13 reviews
4 repeat clients
20 years of experience
Charles Town, WV, 25414

About: Hi, I'm restarting my animal care business. I want to ensure a stimulated experience with a swift pace and consistent disciplined walking style of what I like to refer to as "nose to toes," where the dogs stay no further than my toe, to my sides, or behind me. I also have experience with aggressive dog behavior, so if a single walk is necessary, I can do that. I have been in the animal care business for as long as I can remember, and I know Fairlington very well since I grew up here. I now live in Harper's Ferry in West Virginia. I will be able to track my walks with a phone app that will track your dog's walking pace, distance traveled, and the route we take. I usually do pack walks of 3-5 dogs depending on size, but I can do singles if needed. I'm also able to cat-sit/dog-sit and care for exotics and birds (no insects). I'm flexible because I have my own cleaning/organizing/declutter business. I wake up however early dog might need be let out or pet given meds, and give at least 3 long 30min-hour walks depending on the energy level and few let outs throught the day if needed for young pups or older if bladder is sensitive. Plenty of loves and can work on training or stimulated play time with toys and puzzles. I will be professional and not have any guests over ever, and always keep doors locked when not there and if plants need care I can help with watering. I have 4 animals myself so it's pretty automatic to just add another pet cuz I've cared for multiple animals at a time or drop in visits when needed throughout my day. Whatever the fmaily requests for schedule when to feed, medicate(if needed), amount of walks and play time needed to make sure they're healthy and stimulated. Whenever they're ready for bed, crate if needed requested by parents, and make sure they go outside(dogs) to ensure no accidents throughout the night. I give them just as much love and attention and play as my own. And feed round same schedule unless instructed otherwise. Giving exercise and play time when needed. And kept to routine of crating if owners instruct.

Sitter Profile Image: Aaron F.
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Aaron F.
from
$45
per night
5.0 out of 5 stars
• 3 reviews
15 years of experience
Middletown, VA, 22645

About: I love dogs and can't wait to take care of your furry friend! I have a large home, plenty of room for your dog to stretch out. I have a yellow lab/golden retriever mix who is very friendly. I have a fenced yard (about half an acre) and another 9 acres of unfenced area. I work from home during the week, so will have plenty of time for walks, play-time, etc. I am good with all ages/sizes. I will ensure your dog is comfortable and safe, and has plenty of attention! I work from home so am always around to care for your pets! Will have plenty of potty breaks and play time. If I have to step out I can crate your pet or not, whichever you prefer. I have a fenced in yard I work from home so am always around to care for your pets! Will have plenty of potty breaks and play time. If I have to step out I can crate your pet or not, whichever you prefer.

Sitter Profile Image: Chelsea A.
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Chelsea A.
from
$45
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
15 years of experience
Winchester, VA, 22602

About: I’ve taken care of dogs since I was a child. My family and I grew up with a family dog and then got a puppy in high school that we trained. Even would watch the neighbors pets when they went away. Most recently, I have watched/stayed with a dog when the family traveled. Love all animals, but especially dogs! I work from home and on my own schedule. I have the flexibility to take dogs on walks, bathroom breaks, and even stay with the pet when needed! Working for yourself has great perks when it comes to taking care of our lovely pets. I live in an apartment complex, but have sidewalks for walks. We also have two dog parks. I love staying active, so walks for me are enjoyable! I don’t have any pets of my own currently, so I love being able to love on others pets!

Sitter Profile Image: Katie R.
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Katie R.
from
$100
per night
5.0 out of 5 stars
• 33 reviews
8 repeat clients
24 years of experience
Wardensville, WV, 26851

“Katie was absolutely amazing. Our retriever was quite anxious about us leaving, and she quickly calmed him. He was great with her. Both of the pups were happy and behaved as though we never left. We will definitely be reaching out again!”

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Megan W.
Sitter Profile Image: Dyani C.
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Dyani C.
from
$65
per night
3.5 out of 5 stars
• 5 reviews
14 years of experience
Martinsburg, WV, 25404

About: Ive always loved animals, especially dogs. I grew up on a farm, and I have skills training, and taking care of many types of animals. Im currently working part time, and have plenty of time to check on and watch your pups. I have time on the weekends and weekdays for you. I have lots of space, love, and care for your pets. At my clients home I follow instructions and preferences to care for their pets.

Sitter Profile Image: Olga & Stepan A.
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Olga & Stepan A.
from
$40
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
10 years of experience
Sperryville, VA, 22740

“Olga and Stepan took great care of my two dogs while I was away. They sent me pictures, administered meds, took them for walks, and gave them plenty of affection. One of them was home with the dogs at all times which I am sure they enjoyed since I cannot work from home. I highly recommend them and will definitely request them again.”

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Laura P.
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The median cost per night for house sitting in Winchester is $50

Pet parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

Kristine was great with our 3 dogs! Kept in touch while we were gone. House was clean and sheets were washed and changed upon coming home! I would definitely recommend :)

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Erica C.
House Sitting
5.0 out of 5 stars

Megan did a great job with my dog! She has a relaxed and calming presence that put my dog right at ease, and I highly recommend booking with Megan.

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Hope S.
House Sitting
5.0 out of 5 stars

Cameron did a fantastic job taking care of my baby. She did a good job not only feeding and cleaning up after the dog but she kept her engaged and happy! She always kept me updated and sent me pictures when she came to visit my home. She followed all the instructions well and did a such a great job.

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Samir S.
House Sitting
5.0 out of 5 stars

She was a great fit. She took to understand everything that was needed. A very easy going, down to earth lady. You could not find anyone better. Im thankful for that I hired her hired . Sue would like to thank you.

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David B.
House Sitting
5.0 out of 5 stars

Riona took great care of our 2 dogs, a Bernese Mountain dog and Australian Shepherd. Although our Aussie can be tempermental, and initially barked when she entered the house, Riona handled it with ease and professionalism. She communicated regularly and sent photos. She is so sweet with them - I would definitely have her house sit for us again!!

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Leslie A.
House Sitting
5.0 out of 5 stars

Natalie was great. Well organized, earnest and reliable. JT is a big boy and she was able to handle him. House was well cared for too!

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Laurie P.
House Sitting
5.0 out of 5 stars

Kristina did a fabulous job in taking care of our special girl as well as looking after our home. We highly recommend her and will definitely work with her again!

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Joseph D.
House Sitting
5.0 out of 5 stars

Lovely person who understood our very suspicious kitty and took excellent care of her! Definitely recommend!

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Anne L.
House Sitting
5.0 out of 5 stars

Charlotte was so great! She sent us regular updates and pics of our dogs. She kept our house neat and even put her sheets in the wash at the end of her stay. I felt so comfortable having her here taking care of our fur babies and will use her again and again!

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Donna T.
House Sitting
5.0 out of 5 stars

Drew house sat for my reactive pity mix and I will 100% hire him again. He responded promptly after my initial request, communicated clearly his availability, showed up on time, treated my house as his own, kept me informed throughout his stay with pictures, left my house exactly as I left it. Drew understands dogs needs and the needs of pet parents.

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Suzanne C.
House Sitting
5.0 out of 5 stars

Lauren was absolutely incredible, and I truly couldn’t have asked for a better house sitter. She took amazing care of my two dogs and my cat, and I never once worried while I was away. She spent plenty of time with them each day, so I knew they weren’t being left alone for long periods, and it was obvious she genuinely cared about their well-being. She followed every instruction I left for her carefully and was incredibly attentive to all of their needs. One thing that really stood out was how thoughtful and communicative she was—not only did she keep me updated, but she also stayed in touch with my mom throughout the week so we both knew everything was going smoothly. Coming home, my pets were happy, relaxed, and clearly well cared for, and my home was just as I left it. Lauren is responsible, trustworthy, compassionate, and went above and beyond in every way. I would recommend her without hesitation to anyone looking for someone to care for their pets and home. Five stars isn’t enough!

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Jordan L.
House Sitting
5.0 out of 5 stars

Hailey was great with my fur babies. Her communication was excellent and she sent me pics everyday without me having to ask. When I unexpectedly had to come home early, she was kind and accommodating. A+

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Dorene K.
House Sitting
5.0 out of 5 stars

Susan was the best! So professional and so loving towards my dog! She sent photo and video updates throughout the weekend and we couldn’t have asked for a better pet sitter. She is well experienced and clearly loves pets and will love on yours too. I couldn’t recommend her enough, we will use her again!

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Sydney C.
House Sitting
5.0 out of 5 stars

She took exceptional care of our three older dogs. One who requires insulin twice daily, eye drops, and oral meds. We came back to the house the way we left it and she provided updates. Have already asked about rebooking!

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Kimberly R.
House Sitting
5.0 out of 5 stars

Emily was perfect!!! She came to my rescue at the last minute. She was on time and took great care of my little spoil babies. I will definitely recommend and use her again.

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Mary P.
House Sitting
5.0 out of 5 stars

Autumn did a great job taking care of my babies while I was gone. She was great at communicating and sent me pictures every day. I would recommend.

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Dorene K.
House Sitting
5.0 out of 5 stars

Liza was AMAZING! My prearrange Sitter canceled three hours before I had to leave for a Fourth of July party and Liza was ready to go and eager to help! I am so thankful and grateful! What absolutely be using Liza again!

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LN C.
House Sitting
5.0 out of 5 stars

Kathryn was great. JT can be be a challenge due to size. But it evident that both he and the house were well cared for. We will use her again.

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Laurie P.
House Sitting
5.0 out of 5 stars

ruby was super communicative and was so kind to our pup! would definitely book her to dogsit again :)

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Claire M.
House Sitting
5.0 out of 5 stars

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!

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Nicoll F.
House Sitting
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  • 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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

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Popular requests for house sitting - Winchester

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Sitters in Winchester average 3
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FAQs for House Sitting - Winchester

Frequently asked questions about Rover

The average cost of House Sitting in Winchester on Rover is $56 per night as of October 2026. Most bookings cost between $33 and $83 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 455 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 , 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 .

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 .

sitters on Rover set their own , 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:

  • 92% of sitters can help with special care needs
  • 95% 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.

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