Pet Sitting Winchester

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Over 398
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.

1 / 1
Sitter Profile Image: Kimberly B.
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Kimberly B.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
• 367 reviews
124 repeat clients
8 years of experience
Winchester, VA, 22601

“Kim is the absolute best! It is such a good feeling to entrust your furry family members to someone who clearly loves them too! And, our dogs love her right back! Kim keeps us updated throughout the day, and our babies seem perfectly content upon our return! I HIGHLY recommend her.”

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Cyndi L.
Sitter Profile Image: Stephanie B.
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Stephanie B.
from
$18
per visit
32 years of experience
Winchester, VA, 22601

About: My family lives in downtown Winchester where there are plenty of places to walk. Since I am in a new season of life (semi retired) I wanted to so something I love like walk more and take care of your pet(s). I have been a dog owner for 16 years. I have trained a puppy and helped my first dog all the way through elderly care. Three cats have touched my heart, two cats from kittens through elderly stages. I offer a quiet and comforting hand to all animals. Your companion(s) are God's gift to your family and I would be honored to take care of them. I am currently working part-time for the city transportation division but have a flexible schedule so I can take care of your pet(s). I am an early riser so I don't mind those pets who need morning care. That does mean I go to bed early so I would stop at 8pm. I am a respectful semi retired lady who loves animals. My pets roam around freely at my home. They love their morning routines as I do. If I take care of your pet(s) I will keep whatever routine you have already established with love, safety, and kindness.

Sitter Profile Image: Lisette R.
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Lisette R.
from
$16
per visit
5.0 out of 5 stars
• 85 reviews
34 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: Kathy G.
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Kathy G.
from
$25
per visit
5.0 out of 5 stars
• 59 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: courtney b.
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courtney b.
from
$23
per visit
4.9 out of 5 stars
• 61 reviews
20 repeat clients
20 years of experience
Winchester, VA, 22602

“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: Christopher P.
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Christopher P.
from
$25
per visit
5.0 out of 5 stars
• 17 reviews
3 repeat clients
13 years of experience
Winchester, VA, 22601

About: We provide a special touch of walks, wags and worry free pet sitting! From zoomies to cuddles we can match your fur babies energy level. Apple Pay,Venmo,Cash or in app payments welcome. We’re a meticulously organized couple which permits us a flexible schedule when caring for our fur babies. We’d love to extend the care to your fur babies as well! We recognize that each pet has their distinct personality and we like to honor that. Pelusa, our oldest cat, despite her age, carries a playful kitten soul so we like to dedicate extra stimulating play for her. Our youngest he likes to exert his energy by bird watching and running and jumping around so we’ve accommodated the house for his races since playing 1 on 1 with him does not captivate his curiosity. Just like that we can confidently say we love learning about our clients and their pets personality so we can make the best transition when caring for them that day and so everyone feels seen and included, even the little ones! We also understand pets can be very oriented to habits so we like to know what habits and/or rules you have for your pets so we can respect and abide to those as well!

Sitter Profile Image: Leslie B.
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Leslie B.
from
$13
per visit
3 years of experience
Winchester, VA, 22601

About: Hi! My name is Leslie, and I’m a caring, reliable, and responsible animal lover who would love to help care for your furry family members! I have grown up with dogs my whole life and have been dog sitting for friends and family for about 3 years now. I’m a full time firefighter with a lot of free time on my days off. Whether your pup needs walks, playtime, feeding, companionship, or just some extra love while you’re away, I’m happy to help! I have a ton of flexibility and can assist wherever you need. I look forward to meeting you and your four-legged best friend! 🐾 I currently work as a full time firefighter and I work about 10 shifts a month. On my days off, I stay active with my husband going on hikes, runs, swims, and bikes. I have plenty of time to care for your pets. Note that my schedule is 24 hours on and 48 hours off, so when I’m working I will not be available. I am respectful of your home and will treat your routine with your pets as a priority. I will care for your pets as I would my own and care for their specific needs.

Sitter Profile Image: Kimverly B.
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Kimverly B.
from
$14
per visit
4 years of experience
Winchester, VA, 22601

About: I will provide the best pet care possible ! Your furry family member will be loved and cared for just as you wish! I grew up with so many pets and now am a proud owner of a pup, names oso, as he’s no longer a puppy he will always be treated like one just as our children even all grown up will be our little girls and boys always so are our furry family memebers ! I’m great at tug o war, playing fetch, or just taking a stroll around the neighborhood! I have a very flexible schedule and a great direction follower ! You just let me know what needs your pets require and they will be completely successfully! Thank you hope to hear from your soon I have a full time job but can come before and after. I provide feeding, fresh water, litter box cleaning, playtime, medication administration (if needed), and plenty of updates with photos so you can have peace of mind while you’re away I take the time to earn their trust and follow their routine.I do have a cat and dog, so my house onboarding is available on weekends only.

Sitter Profile Image: Gabrielle I.
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Gabrielle I.
from
$25
per visit
8 years of experience
Winchester, VA, 22601

About: I have eight years of experience caring for cats. I absolutely adore cats, and having had a cat of my own for almost 10 years now, I know how beloved and valued they are by the families I help. Throughout my years of cat sitting, I have cared for cats of all ages, administered medications, cleaned multiple litter boxes, and, of course, entertained with cat toys! Your need for pet care is never a burden. I take true joy in having the opportunity to meet and care for new furry friends! I currently work as a fitness specialist and personal trainer in medical fitness, so I have full availability on the weekends and my schedule with training clients largely allows me to check-in on pets throughout the day. I am unable to keep cats in my home; however, I am happy to travel to clients' homes and stay overnight to provide care. In my previous experiences cat sitting, I often check-in multiple times daily throughout my work day and stay in the home each night. I provide drop-in or house-sitting services.

Sitter Profile Image: Jose O.
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Jose O.
from
$15
per visit
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: Kristen C.
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Kristen C.
from
$15
per visit
19 years of experience
Winchester, VA, 22601

About: I have been a pet owner for most of my life. I volunteered at the SPCA while I was in college, and I thoroughly enjoy interacting with animals. I will care for yours as I cared for my own! While my daughters are in school, my day is open! I can visit, walk, and play with your pet while you’re at work, so you won’t have to worry if they’re bored or lonely. I will come to your house to walk, feed, and/or play with your pet. We can discuss your pet’s needs at any time.

Sitter Profile Image: Myahrissa R.
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Myahrissa R.
from
$20
per visit
5.0 out of 5 stars
• 128 reviews
26 repeat clients
4 years of experience
Stephenson, VA, 22656

“Mayahrissa is an excellent pet sitter. From our first meeting I could tell she really cares about animals and although I was a little nervous leaving my 3 month old puppy with a sitter for the first time, I immediately trusted Mayahrissa. During her visit, she followed all the care directions and sent me lots of pictures. My dog really likes her. She has a calm demeanor which puts pets at ease. I highly recommend her.”

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Lorena C.
Sitter Profile Image: Cameron W.
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Cameron W.
from
$18
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
7 years of experience
Winchester, VA, 22601

About: I have a love and understanding for all animals! I have trained my own and have learned so much through them. I have a lot of experience with dogs with behavioral issues. I am a college student with a lot of free time. My evenings are free and I have a lot of gaps during the day! I would love to get out on walks with dogs in my gaps. I have my own dog to keep yours company if that is something you would like. If not, he can stay with his other mama when your pup is over! Dogs will get full exercise and enrichment when staying with me. We will be in a fenced in yard running around and go on serval walks throughout the day.

Sitter Profile Image: Gabby T.
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Gabby T.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
• 199 reviews
32 repeat clients
5 years of experience
clearbrook, VA, 22624

“Gabby took excellent care of our animals while we had to go out of state. I could tell from her pictures and from how they were acting when we got home that they really enjoyed their time with her. We'd absolutely book Gabby again in the future!”

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Jeremiah S.
Sitter Profile Image: Jessica J.
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Jessica J.
from
$20
per visit
20 years of experience
Stephens City, VA, 22655

About: Animals have always been a big part of my life! With over 20 years of experience caring for my own pets and family members’ animals, I understand just how much our furry friends mean to us. ❤️ I'm currently a proud pet mama to two pit bulls, ages 13 and 1, so I'm no stranger to everything from playful puppy energy to the extra patience and gentle care our senior pets deserve! I also have experience caring for cats and other animals, and I love getting to know each pet's unique personality and needs. I know how important it is to feel confident that your pets are in good hands when you're away. My goal is to provide dependable, attentive, and loving care while treating your pets like part of my own family! 🐾 Pet care is already a natural part of my everyday routine! As a mom of five who homeschools and works primarily from home, I have a flexible schedule that allows me to incorporate pet care throughout my day. Caring for our own two dogs is already part of our family's daily rhythm, so I'm very comfortable balancing feeding, walks, playtime, and plenty of love and attention alongside our regular activities. Being home much of the week gives me the flexibility to provide dependable, attentive care while making sure each pet's individual needs and routines are respected. I love spending time outdoors and would be happy to make your furry family member part of that time, too! I provide loving, attentive care in your pet’s own home, where they feel most comfortable! I follow their regular routines, including feeding, walks, playtime, and any special care needs, while treating your home and pets with the utmost respect.

Sitter Profile Image: Marian K.
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Marian K.
from
$15
per visit
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: Mark R.
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Mark R.
from
$24
per visit
5.0 out of 5 stars
• 5 reviews
35 years of experience
Winchester, VA, 22601

“Mark took excellent care of our cat, Lola, when we were away for a week vacation! He sent us regular photos of her and we knew she was in good hands. We would definitely use him again in the future!”

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Catherine F.
Sitter Profile Image: Natasha L.
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Natasha L.
from
$22
per visit
5.0 out of 5 stars
• 11 reviews
2 repeat clients
20 years of experience
Berryville, VA, 22611

“Easy to work with and very responsible”

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Ray M.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 47 reviews
11 repeat clients
10 years of experience
Cross Junction, VA, 22625

“Meet and greet. So wonderful to meet Jennifer. She was very quick to understand things. I’m so grateful to have someone to call on for various visits for our pets. Thank you for your time today Jennifer.”

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Jody S.
Sitter Profile Image: Sherry R.
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Sherry R.
from
$15
per visit
5.0 out of 5 stars
• 28 reviews
8 repeat clients
3 years of experience
Stephens City, VA, 22655

“Sherry was amazing! We decided to go on a last minute trip and she met with us the night before we left. She was so nice and a joy to be around so we knew Charlie would love her! This was our first time leaving him but we were reassured by her personality. She did everything we wanted and more. We can't thank her enough and we highly recommend her! We will definitely use her services in the future!”

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Kristen P.
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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

Taylor was timely, pleasant, responsive and spent time playing with Annie. Would definitely reach out again!

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

Hannah did a great job taking care of our cat! 10/10 no notes. She kept us updated and informed on every visit and took some really cute photos. I’m also happy she got him to come out of his shell in the later visits. Thanks for everything! ☺️we will definitely reach out again for future visits!

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Sophie G.
Drop-In Visits
5.0 out of 5 stars

Kim watched my shy cat while I was out of town. She was a great sitter with lots of communication! I would book with her again for future trips

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Kathleen H.
Drop-In Visits
5.0 out of 5 stars

I had Christa watch my beloved cat, Kitty, while I was away on an extended trip, she was very dedicated to attending to Kitty’s needs while I was away including playing with her, giving her treats, and making sure she was well fed. Christa was also adamant about keeping the lines of communication open and informing me of important details like when she would be arriving to my home.

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

Megan was wonderful with communication and taking care of our pups. I felt completely relaxed during our trip knowing they were in her care. I would 100% recommend her to others and use her again in the future. :) thank you so much!!

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

Isabella is always so wonderful! She sends regular updates and goes above and beyond typical cat sitter duties. I use her every single time I travel 😊

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

Susan is so sweet, and Franky really likes her. I feel great knowing my big guy will be in good hands.

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Seven R.
Drop-In Visits
5.0 out of 5 stars

From our very first meeting, I could tell Alex was completely comfortable with our big, overly excited boy. Franky loves his walks and having someone to spend time with, and I really feel like Alex is going to be a wonderful friend and walking buddy for him. 🐾❤️

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Seven R.
Drop-In Visits
5.0 out of 5 stars

Charissa is the absolute best! It’s so easy to travel knowing that our pets are well-cared for when we’re gone. Super reliable and punctual. Can’t say enough good things!

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

Julianna was great! Even found my cats who are hard to find. Sent regular updates and pictures. Thanks so much. You were a lifesaver.

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Julie H.
Drop-In Visits
5.0 out of 5 stars

I think this is my third review for Alexis? But she she and I have known each other for a few months now, and she has been a delight with sitting for my dog. Would recommend very highly for your home too.

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

Lisette is fantastic! Prompt communication and my feline was quite happy to see her while we were away. Everything went smoothly, and I had complete peace of mind while on out trip. Highly recommend!

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Mercedonius
Drop-In Visits
5.0 out of 5 stars

Drew was awesome- super communicative, timely and caring. He was proactive about reaching out, and sent multiple pictures while we were away. I’ll definitely book with him again!!

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Claire M.
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

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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How to book pet sitting

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Popular requests for pet sitting - Winchester

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Sitters in Winchester average 6
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FAQs for Pet Sitting - Winchester

Frequently asked questions about Rover

The average cost of Pet Sitting in Winchester is $24 per visit as of November 2026. Most bookings cost between $13 and $29 per visit. On Rover, 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 November 2026, there are 860 sitters on Rover offering Pet Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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:

  • 91% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 98% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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