Pet Sitting Winchester

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Over 443
pet parents in Winchester have booked pet sitting

Winchester, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Hannah D.
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Hannah D.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
91 reviews
22 repeat clients
10 years of experience
Winchester, VA, 22602

About a week before we left on vacation our orange kitty was diagnosed with a urinary issue and Hannah rose to the occasion to give him his medicine even though that’s not something that we were able to go over during our meet and greet. Thank you so much for taking care of our kitties while we were away, Hannah!

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Lindsay M.
Sitter Profile Image: Susan B.
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Susan B.
from
$13
per visit
5.0 out of 5 stars
4 reviews
15 years of experience
Winchester, VA, 22601

About: I’ve loved animals my whole life, and I’ve had the pleasure of living with, and pet sitting for multiple cats and dogs. I’ve done both kitty and dog meds, so if you have a high maintenance fur child like me, I’ve got you covered!! If you trust me with your fur baby, I promise I will love them as much as I love my own!! I work from home, so I have a lot of flexibility. Mornings are more difficult for me, but I can definitely work with you to find what’s best for the pets! My own pets are high maintenance, so I am definitely able to work with your pets needs. I crate my own dog, and give both my dog and cat meds and supplements. I don’t have any human children so my pets are my children. I will give your pet the love, attention, and care I give my own!!

Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
15 years of experience
Stephenson, VA, 22656

Allison was fantastic with my two cats this weekend! Timely, communicative, and trustworthy :) She was also great about my last-minute booking, since I’d just moved to the area and had to unexpectedly be out of town. Would book her again!

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Jessica K.
Sitter Profile Image: Kimberly B.
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Kimberly B.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
341 reviews
116 repeat clients
8 years of experience
Winchester, VA, 22601

Was able to get Kimberly to come out at the last minute while we were unexpectedly away. She made the difficult journey to find our house and was able to help make sure our pets and property were ok. We are very appreciative of her being able to come out and help us!

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Heather W.
Sitter Profile Image: Alexsys T.
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Alexsys T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
325 reviews
129 repeat clients
7 years of experience
Clear Brook, VA, 22624

As always, Alexsys is great! She's communicative, on time, and takes great care of my cats! I always know my fur babies are in good hands with her.

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Lillian R.
Sitter Profile Image: Lisette R.
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Lisette R.
from
$16
per visit
5.0 out of 5 stars
80 reviews
32 repeat clients
6 years of experience
Winchester, VA, 22601

She did an excellent job with my two cats! I can tell they were well taken care of and were just as happy as I left them! No messes either, which was a first!

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Cooper B.
Sitter Profile Image: Kate-Lynn T.
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Kate-Lynn T.
from
$25
per visit
10 years of experience
Winchester, VA, 22601

About: I have extensive experience caring for pets, having watched my aunt’s cats regularly and cared for many animals of my own over the years. Although I lost access to my old Rover account, I’ve been providing reliable and loving pet care for quite some time. I understand the importance of attention, safety, and affection, and I’m committed to ensuring every pet feels comfortable and happy while in my care. I have 3 to 4 days off each week, which gives me plenty of time to dedicate to pet care. Whether it’s daily walks, feeding, playtime, or simply providing companionship, I’m able to give pets the attention and care they need without feeling rushed. This flexibility means I can accommodate various schedules and be fully present to ensure each pet’s comfort and happiness. I care for cats in my home, providing a calm and cozy environment where they feel safe and loved. For dogs, I offer care at your home and take them out for walks with a wonderful local walking community. There’s also a dog park nearby where dogs can socialize and play. I’m dedicated to making sure every pet gets the attention, exercise, and comfort they need.

Sitter Profile Image: Alex M.
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Alex M.
from
$14
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
15 years of experience
Winchester, VA, 22601

Alex was great while dropping in on my dogs. She went above and beyond what was asked and the pups loved her.

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Cassidy F.
Sitter Profile Image: Christa K.
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Christa K.
from
$15
per visit
5.0 out of 5 stars
19 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22601

I am very happy with Christa! She did an amazing job with my pups. Bo and Sheena are very happy too. This was my first time using this service and I’m so happy that I found Christa. It’s not easy for me to leave my pups with anyone. Thank you Christa for being so kind and friendly to my pups. I will definitely be using these services again and request for Christa.

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Patricia V.
Sitter Profile Image: courtney b.
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courtney b.
from
$17
per visit
5.0 out of 5 stars
52 reviews
15 repeat clients
20 years of experience
Winchester, VA, 22601

Courtney was absolutely wonderful with our two dogs! She spent extra time; she fed and gave treats,and she was affectionate and gentle with them. She went way beyond providing a great experience, and we will definitely book her again. One dogs love her, and we trust her with their care. It's clear from talking to her that she truly loves animals!

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Veronica G.
Sitter Profile Image: Alexandra L.
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Alexandra L.
from
$16
per visit
4 years of experience
Winchester, VA, 22601

About: I’ve been volunteering at my local animal shelter for the past two years, where I’ve had the opportunity to work with dogs and cats of all ages, sizes, and personalities. This experience has taught me how to recognize different temperaments, build trust with shy or anxious animals, and confidently care for energetic pets as well. I genuinely enjoy getting to know each pet’s unique personality and always strive to make them feel safe, comfortable, and loved while they’re in my care. I’m a PA (Physician Assistant) student who absolutely loves animals and enjoys spending my free time caring for pets. My class schedule keeps me busy during the day on weekdays, but I’m available for early morning (before 7am) and evening visits (after 5pm) on weekdays, open on weekends, and many overnight stays. Your pet’s safety, comfort, and routine are my top priorities. I know that every pet is different, so I take the time to learn about their personality, preferences, and any special needs before each booking. I carefully follow all feeding schedules, medication instructions, exercise routines, and house rules to help them feel comfortable and maintain their normal routine.

Sitter Profile Image: charlotte g.
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charlotte g.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
6 reviews
4 repeat clients
8 years of experience
Winchester, VA, 22601

Charlotte is very knowledgeable and reliable. She took good care of my cats while we were out of town. I will book her again and highly recommend Charlotte for pet sitting services.

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Susan T.
Sitter Profile Image: Charissa L.
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Charissa L.
from
$17
per visit
5.0 out of 5 stars
17 reviews
5 repeat clients
15 years of experience
Winchester, VA, 22601

Charissa is amazing! Our plans changed more than once and she stayed flexible working with us. We received beautiful pictures of all our dogs and updates for every visit. Her rates were very fair and she even cleaned up without being asked! We will be recommending her services to family and friends while also asking her back to our home. We love her and our pups do too!

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Drew B.
Sitter Profile Image: Taylor R.
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Taylor R.
from
$13
per visit
15 years of experience
Winchester, VA, 22601

About: I’ve taken care of dogs and cats of all sorts. I grew up with small, medium, and large dogs as well as indoor and outdoor cats. I’ve also grown up caring for animals from a variety of backgrounds- fosters, rescues, you name it. I genuinely love spending time with animals and since I can’t have one of my own this seems like a great way to connect with pets and offer my services. I’m happy to come meet any animals in advance to make you more comfortable. I currently work remotely 90% of the time so this gives me a lot of flexibility to walk and take care of animals during work day hours if needed. I’m very good with following whatever directions will make you and your pets feel the most comfortable in your homes and out on walks.

Sitter Profile Image: Shaghayegh H.
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Shaghayegh H.
Star Sitter
from
$29
per visit
5.0 out of 5 stars
189 reviews
50 repeat clients
15 years of experience
Winchester, VA, 22602

We had a family emergency and had to leave our Dog Piff at home and Shaghayegh was amazing! She really went above and beyond for my family and made sure our dog was taken care off. She let us know before and after she left and always sent pictures everyday! I would 100% use her again!

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Victoria o.
Sitter Profile Image: Drew B.
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Drew B.
from
$12
per visit
5.0 out of 5 stars
1 review
8 years of experience
Winchester, VA, 22603

About: Everyone calls me when they need a reliable and dedicated pair of hands to watch over their children. Yes, I treat every dog like a furry child. I've helped raise dogs from 6 weeks to 16 years old. The young and the old need a little more attention and I'm happy to help. Those terrible 2's just need extra attention, and I'm happy to provide that too! I love all animals and will probably treat the kids like royalty. I prefer the company of dogs than my friends, they could vouch for that! I'm both loving and also stern because I've raised both labs and pitties. They require different types of parenting techniques, and I am equipped to handle anything. I work full time, Monday through Friday, 9 to 5. I'm happy to use my work breaks to check on animals for those who need the extra attention. My availability will be based around my work and my 2 kiddos at home. I can adjust weekly routines to incorporate pickup/drop offs, stop in visits, after work walks, or overnight stays. I treat dogs like they are our kids. I talk to them, I cuddle with them, and I use positive reinforcement to train good habits. I've helped raise a dozen dogs and each dog likes to show you how they like to be treated. I learned this lesson the hard way when I was raising dogs and had to learn different techniques to train each of them individually. Labs learn and function much different than bulldogs and pitbulls. I treat each dog the same regardless of size or attitude. Though I may give them some attitude when mouth off, like I do with my pitty at home (lol). I'm a safety first kind of person when it comes to our kids. So I tend to lean on the side of caution and extra equipment when interacting with most dogs. I always keep extra dogs supplies in my truck at all times as I have been known to that guy who stops traffic to try to rescue a dog. I've done this probably 6 or 7 times.

Sitter Profile Image: Kathy G.
Verified Background Check
Kathy G.
from
$20
per visit
5.0 out of 5 stars
58 reviews
18 repeat clients
30 years of experience
Winchester, VA, 22601

Kathy was so responsive and reliable! She took great care of our dog and gave detailed info as well as pictures after all of her visits! we will definitely use her again ☺️

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Meredith C.
Sitter Profile Image: Allison B.
Verified Enhanced Background Check
Allison B.
from
$25
per visit
5.0 out of 5 stars
19 reviews
5 repeat clients
10 years of experience
Winchester, VA, 22602

About: Hey there my name is Allison and I am a huge animal lover! I will love on your fur babies while you are gone and make sure they have what they need! As someone that has every pet but a dog of her own and has always wanted one, I will completely take advantage of the time I get with yours! I am comfortable with whatever is in need feeding, walks, backyard play, even just hanging out at the house and keeping your animal company! I have experience with a wide range of animals and I will make sure your needs are met! I am so excited and looking forward to meeting you and your sweet fur baby! Whatever animal comes my way I will make sure they are taken care of!

Sitter Profile Image: Alex H.
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Alex H.
from
$18
per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
10 years of experience
Winchester, VA, 22601

We rehired Alex to look after our big dog Rocky again for a week while we celebrated our anniversary. He did an amazing job and kept us updated with pictures of Rocky and rocky looked like he was having a blast in all the pictures. Alex played fetch with him in our yard daily and made sure Rocky had enough toys to play with. We came home to a happy dog and we are very grateful we could celebrate our anniversary without worrying about how Rocky was faring back home thanks to Alex!

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Destiny W.
Sitter Profile Image: Emily F.
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Emily F.
from
$13
per visit
6 years of experience
Winchester, VA, 22601

About: Available in evenings and weekends. I am reliable, responsible and always on time. I love all dogs and I appreciate all the quirks that come with their individual personalities. I have loved animals since I was young, and I volunteered for a pet shelter in the summer when I was younger. Although I am currently a cat owner, I love all furry animals and I have to greet every dog I meet on the road. I am looking for part time work and this would be a great opportunity to utilize my free time and my love for canines and kitties. I have three cats that are basically like my children, but I adore dogs and would love the opportunity to interact with them daily or weekly. I have free time on my work from home days as well as weekends to assist other dog/cat owners. I do not have a fenced yard, but I live in a community that has a lot of pathways and green space. Within my apartment, I can keep my cats separate if needed but happy to let the dogs explore and get comfy in my space. I am very courteous of other people's space and preferences.

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The median cost per visit for pet sitting in Winchester is $20

Pet parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

Hannah followed our feeding/care directions and showed our Olive lots of love and pets. Olive seemed relaxed when we got back home, which was relieving having seen her very stressed when we’ve not been able to take her with us previously. Thanks Hannah!

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Nicola W.
Drop-In Visits
5.0 out of 5 stars

Such a trustworthy and caring cat sitter. So grateful for her attention to detail and genuine care for my senior cats.

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Kelly N.
Drop-In Visits
5.0 out of 5 stars

she did such a great job with my cat penelope. great at her job and also very nice person! will definitely book with her again next time i’m out of town :)

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Amelia W.
Drop-In Visits
5.0 out of 5 stars

Charissa is the best! She is super reliable. We are so thankful we have found someone to regularly take such great care of our furry family members!

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Ashley M.
Drop-In Visits
5.0 out of 5 stars

Alexsys has been with my dog and I since Jan 2025- she’s responsive to messages, concerns and flexible with me like when I had to take a 6 week hiatus due to house renovations forced me to temporarily move out. I really appreciate her communication style and all of the pictures she takes when she visits 🌻

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Denise L.
Drop-In Visits
5.0 out of 5 stars

Always super sweet and helpful! She is super responsive and someone we can always rely on to take good care of our pups- even for our last minute requests 😊

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Bridget K.
Drop-In Visits
5.0 out of 5 stars

Charlotte is very knowledgeable and reliable. She took good care of my cats while we were out of town. I will book her again and highly recommend Charlotte for pet sitting services.

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Susan T.
Drop-In Visits
5.0 out of 5 stars

Alyssa went above and beyond to give my cat love and attention. She followed instructions well and left the house in good shape.

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Kate S.
Drop-In Visits
5.0 out of 5 stars

Lisette did a great job of taking care of our cats while we were away. Fantastic at communication ( both responding to and asking questions). We would highly recommend her and plan on using her again the next time we are out of town

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Denis D.
Drop-In Visits
5.0 out of 5 stars

Karen was great! We had a trip planned and Whiskey had been sick since November. Thought he would get better but still had a lingeri g cough. We had another sitter lined up who had their own dog and we didn't want that dog to get sick too. I found Karen last minute to come to our home and take care of Whiskey with dropins. She did such a great job and kept us informed on his coughing. Thank you so much!

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Michelle R.
Drop-In Visits
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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
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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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Meet local sitters who will treat your pets like family

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Popular requests for pet sitting - Winchester

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Sitters in Winchester average 5
repeat pet sitting clients

FAQs for Drop-In Visits - Winchester

Frequently asked questions about Rover

The average cost for Pet Sitting in Winchester on Rover is $22.2 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 902 sitters on Rover offering Pet Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winchester stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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.

Yes, you can find sitters who have experience with handling special pet needs in Winchester. On Rover:

  • 93% of sitters can help with special care needs
  • 99% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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.

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