Dog Walking Winchester

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Over 21
pet parents in Winchester have booked dog walking

Winchester, Find top rated dog walking

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

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Sitter Profile Image: Lawton B.
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Lawton B.
from
$17
per walk
4.8 out of 5 stars
• 23 reviews
12 repeat clients
10 years of experience
Ballwin, MO, 63011

“Very nice and friendly, and Scottie really loved her. He came back tired after his walk, which shows he had a great time. We had a very positive experience and would definitely book again”

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Daniela G.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$18
per walk
1 repeat client
20 years of experience
Chesterfield, MO, 63017

About: I have a perfect record that includes over 100 five-star reviews on another platform and am taking my skills and experience to this one. I've always had dogs and always connected with animals and friends and family have recognized that affinity and felt comfortable and trusting their fur babies to my care over the years. I've worked with shy dogs, anxious dogs, aging dogs, dogs with high medical needs, puppies, power breed dogs, tiny dogs, and pretty much any other kind you can imagine. I'm looking forward to giving your pet the same high level of care! I have a flexible schedule that I control, so I have a lot of availability to help you care for your pets. I don't even mind the early morning or late evening walks! I have many regular clients, and they tend to pick me when they need someone reliable (to care for their pets when they're away, to show up on time for a 6am walk before an important procedure, to care for a dog who needs extra patience or care for medical needs, etc.). I was a store assistant manager for 15 years, so I know how to keep calm in emergency situations and understand the responsibility of having people who are relying on me. I also have a musical background, so I'll probably end up singing to your animals like a Disney princess at some point.

Sitter Profile Image: Ashley H.
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Ashley H.
from
$17
per walk
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Ballwin, MO, 63021

“Amazing!”

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josh g.
Sitter Profile Image: Amy H.
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Amy H.
from
$18
per walk
5.0 out of 5 stars
• 2 reviews
10 years of experience
Central West End, Ballwin, MO, 63011

About: I’ve had cats my whole life and love everything about them! I’ve cared for kittens, adults, seniors, and multiple pet households. I have experience with post-op care, cat introductions, and indoor/outdoor cats. I also have experience taking care of young and senior dogs, including administering medication and interacting with cats. Housesitting - I can’t be there 24 hours a day because I have my own pets, but we can discuss how much I need to be away. I work full time from home, mostly available evenings and weekends, daytime if my schedule allows. I’m a night owl so late night visits are okay! I go at your pet’s pace and provide a safe, loving environment so they gain my trust. I go by their usual routine/ habits as not disrupt their routine.

Sitter Profile Image: Sydney B.
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Sydney B.
from
$18
per walk
6 years of experience
Manchester, MO, 63021

About: I’ve been surrounded by animals my entire life—growing up with a variety of family dogs and a cat, I’ve learned how important it is to understand and honor each pet’s unique needs. I currently have one dog of my own: a 6-year-old mini Aussie/Heeler mix who struggles with reactivity and anxiety. These experiences have truly shaped my approach to pet care, emphasizing the importance of ongoing education and compassion. I dedicate time every day to working with my mini Aussie/Heeler and also bring in a professional trainer to help him thrive. I believe that every animal deserves patient, tailored care and that understanding their individual experiences makes all the difference. Although I don’t offer boarding in my home (to ensure my own dogs’ safety and comfort), I’d love to bring this same level of knowledge and dedication to caring for your pet in their home environment! I’m available all day and night on Wednesday, Fridays, Saturdays, and Sundays. During these days, I’m fully dedicated to caring for your pet—whether that’s daily walks, playtime, or simply making sure they feel loved and secure. Because I structure my days around my own dogs’ routines—training, walks, and enrichment—I’m well-prepared to ensure your pet gets the same level of dedicated care and companionship in your home- Because I have a male dog that is highly sensitive due to reactivity, I don’t offer boarding in my home. I trust my dog, but I’d never risk another pet’s safety—so I prefer to provide care in your home, where your pet is most comfortable. In your home, I’ll follow your pet’s usual schedule and rules—whether that’s structured playtime, daily walks, or quiet companionship for a senior pup. I know how crucial it is for animals to feel safe and secure, and I bring that same level of education, patience, and understanding to every pet I care for. I’d love to be a trusted helper in your pet’s life, making sure they’re healthy, happy, and getting the kind of care they deserve.

Sitter Profile Image: Amber K.
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Amber K.
from
$30
per walk
5.0 out of 5 stars
• 34 reviews
15 repeat clients
10 years of experience
Ballwin, MO, 63021

“This is the second time I’ve hired Amber for dog walking and just like the previous time, she did a great job, She’s very skilled with my senior dog and her visits are usually the highlight of my dog’s day. She’s reliable and efficient, with great communication through the Rover app. I highly recommend Amber!”

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Emily T.
Sitter Profile Image: Brody Z.
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Brody Z.
from
$16
per walk
5.0 out of 5 stars
• 7 reviews
3 repeat clients
12 years of experience
Ballwin, MO, 63021

“Brody has been very helpful, communicative, and my dog loves him.”

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Barbara G.
Sitter Profile Image: Callie L.
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Callie L.
from
$30
per walk
5.0 out of 5 stars
• 106 reviews
32 repeat clients
10 years of experience
Chesterfield, MO, 63017

“Our first experience with Rover was pretty rough so it has been several years since I’ve used it…but our sitter graduated and is heading out of state for college so I started looking for another sitter. Callie has done a great job, and has been punctual, thorough, and most importantly she is really good to our fur babies. I’ll gladly become a repeat client, thanks very much for taking exceptional care of our doggies, Callie.”

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Darrell And Katie C.
Sitter Profile Image: Perri E.
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Perri E.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 93 reviews
27 repeat clients
10 years of experience
Ballwin, MO, 63021

About: I'm a caring person who will pay attention to your pet's needs and spend time with them. I had a dog for 6 years before she passed away. She was a German Shepard chow who loved going on walks in the park. I love being outdoors, whether for business or personal health, Disney, and cooking. I follow instructions to a T and will protect your pet at all costs! When house sitting, I always treat the house better than I would treat my home. I clean up after myself, and will provide my own food as I care for your home and pet. I am willing to stay at your house 24/7, while you're away, if you desire it. You will not be disappointed with me as your sitter! My schedule is rather open and quite flexible. I can provide care to cover all your needs; be it a short walk or days to weeks for your vacation! I double-check all doors in my client's homes throughout my stay. I've had no pet break-outs or escapes yet and I will keep it that way. I make sure to keep all human foods out of reach to pets and clean up all my trash. No one is eating trash on my watch

Sitter Profile Image: Blanca B.
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Blanca B.
from
$20
per walk
5.0 out of 5 stars
• 12 reviews
2 repeat clients
18 years of experience
Ballwin, MO, 63021

“Blanca was great! We will definitely use her again in the future.”

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Allie W.
Sitter Profile Image: Brianna I.
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Brianna I.
from
$20
per walk
5.0 out of 5 stars
• 1 review
5 years of experience
Ballwin, MO, 63021

About: Hi, I’m Brie! I’ve cared for dogs of all sizes—from volunteering as a dog walker at the APA shelter to sitting for friends, family, and neighbors. I’m also a college cross country and track athlete, so I love running with high-energy pups who need more than just a stroll. Whether it’s playtime, long walks, or snuggles, I tailor care to each dog’s personality. With two dogs of my own, I know how important it is to find someone reliable, active, and loving. Your dog will be treated like family! Weekdays: Dog walking & drop-in visits Weekends: Overnight sitting & extended care Winter & Summer Breaks: Open availability for sitting, walking, and extended care Also available in Webster Groves Your dog’s wellbeing is my top priority. I create a calm, secure environment where pups feel at ease—whether we’re out for a walk or relaxing at home. I follow your care instructions closely, keep routines consistent, and always prioritize safety on walks and during play. With years of experience and two dogs of my own, I understand how important trust is. I treat every dog like family, offering gentle guidance, positive reinforcement, and a space where they can thrive physically and emotionally

Sitter Profile Image: Elizabeth H.
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Elizabeth H.
from
$16
per walk
4.9 out of 5 stars
• 59 reviews
15 repeat clients
30 years of experience
Ballwin, MO, 63011

“Elizabeth is wonderful! She really helped me out with a quick work trip and my fur babies are always so happy when I get home. I will certainly be rebooking for my next trip!”

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Christy R.
Sitter Profile Image: Molly D.
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Molly D.
from
$18
per walk
10 years of experience
ellisville, MO, 63021

About: Just reactivated my Rover account in June, 2026. I am a dog person. I have two dogs, Clover and Nova which are 70+ pound husky/ Aussie mix dogs that will play hard and sleep harder. I will give your pup tons of attention, play time, and can work on training if needed as well. I love training my dogs as well as other dogs, so if you’re looking for a trusted dog walker with training experience I’m ready to help. Look forward to meeting you and your dogs. I work long days and most evenings and looking to walk dogs on my lunch break close to my office. I love walking as I walk my dogs multiple times a day. I will always leash your dogs on walks. I am familiar with the gentle leader leash and training no-pull harness. I can handle dogs that may be aggressive and will go to the other side of the sidewalk if your dogs aren’t friendly with other dogs.

Sitter Profile Image: Michael & Beth H.
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Michael & Beth H.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
• 270 reviews
64 repeat clients
35 years of experience
SAINT LOUIS, MO, 63122

“Michael has been so great to work with. Always communicates very well, sends photos, and has helped me a lot during my busy schedule. I’d recommend him to anyone!”

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Damion F.
Sitter Profile Image: Andrea W.
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Andrea W.
from
$20
per walk
4.6 out of 5 stars
• 11 reviews
1 repeat client
16 years of experience
Valley Park, MO, 63088

About: Charismatic and outgoing animal lover with 16 years experience owning pets, and hundreds of hours volunteering at the humane society in 3 different states. I grew up with cats, but could not own a dog until I moved out on my own, so I quickly got my first baby Alice the first chance I could. My fur babies include a 13 year old sweet beagle mix, Alice 🌈 and two gentle loving cats, Poppy and Millie. All of my animals have been around other animals their whole lives and get along with all creatures. I prefer not to board cats, but can keep your cat in a closed bedroom for their stay. I would love to open my doors to help out families in need of a more personal way to board their pets when they are away. Your animals must get along with cats and small children. I have a very flexible schedule so I have the ability to care for your pet throughout the day, depending on your pets individuals needs. My pets have free range of the house. Visitors dogs can be crated if needed or have free range of the house if ok left unsupervised.

Sitter Profile Image: ana G.
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ana G.
from
$18
per walk
15 years of experience
Chesterfield, MO, 63017

About: There’s nothing like the love you receive back in a single look. I’ve had dogs my entire life—being a pet lover is simply part of who I am. To me, they’re not just pets—they’re a special part of our lives. With 13+ years working in a pet care company and over 2 years fostering 21+ dogs, I bring both professional expertise and real-life experience. I’ve cared for dogs of all ages, personalities, and needs—both small and large breeds, from 9-week-old puppies to senior dogs. I’ve also regularly cared for dogs of neighbors and friends, building trusted relationships within my community. I understand that leaving your dog with someone else is a big decision. My goal is to give you complete peace of mind, knowing your dog is safe, understood, and genuinely cared for. I’m patient, attentive, and especially comfortable helping dogs adjust, feel at ease, and build confidence. I truly love how every dog is unique—their personality, their energy—and getting to know each one is something I genuinely love. At home, I have two well-trained dogs—Valentino (Golden Retriever) and Romeo (Australian Shepherd)—who help foster dogs learn positive behaviors and feel comfortable. I treat every dog as my own, making sure they feel safe, relaxed, and happy—so you can feel confident and at ease while you’re away. I’m available for walks Monday through Friday from 9:00 AM to 2:30 PM, and generally on weekend mornings. My schedule allows me to provide consistent attention and reliable care during these hours. I aim to follow your dog’s usual routine as closely as possible, so they feel comfortable, secure, and well cared for while you’re away. I can be flexible for additional times when needed—just feel free to reach out and we can coordinate what works best for you and your dog. Your dog’s safety and comfort are my top priorities. I provide a calm, structured, and loving environment where dogs can feel secure and at ease. I have a fenced yard for safe outdoor time, and two well-trained, friendly dogs—Valentino (Golden Retriever) and Romeo (Australian Shepherd)—who help create a balanced and positive environment, especially for dogs who benefit from socialization. With my background fostering over 21 dogs, I’m experienced in reading dog behavior, managing different temperaments, and helping dogs adjust smoothly. I can also follow specific instructions such as crate training, feeding routines, or medications if needed. I treat every dog with care, attention, and responsibility—so you can feel confident your dog is in safe and capable hands.

Sitter Profile Image: Perrin W.
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Perrin W.
from
$30
per walk
5.0 out of 5 stars
• 7 reviews
2 repeat clients
40 years of experience
Ballwin, MO, 63021

About: I had pets as child and always have had dogs and cats as an adult, and felt it important for children to be around pets I am retired, arise early and love to be outdoors. I especially like walking, might as well have a dog with me when I walk. I will follow all guidelines given to me by the pet owner, will have contact with the owner before and while caring for their pet/pets.

Sitter Profile Image: Elizabeth G.
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Elizabeth G.
from
$20
per walk
5.0 out of 5 stars
• 75 reviews
22 repeat clients
18 years of experience
Fenton, MO, 63026

“Of course humans weren’t there but but we texted, saw picture and a video and felt that Sophie was in extremely competent hands! 5 Stars for you Elizabeth!”

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Deb N.
Sitter Profile Image: Kamren A.
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Kamren A.
from
$25
per walk
5.0 out of 5 stars
• 2 reviews
8 years of experience
Ballwin, MO, 63021

About: I've taken care of dogs for several years. I am happy to stay at your home as well as just visit. I'm active and would love to exercise your pet and take them out frequently. I will keep you updated on how they are doing and send pictures. If I am caring for your pet I will work off your and their schedule. I can get up early and let them out as much as they are needing. I have a dog and I frequently watch her when my parents are out of town, take her on walks, let her out, feed her and make sure she gets the attention she needs. I am trustworthy and dependable.

Sitter Profile Image: Julianna B.
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Julianna B.
from
$15
per walk
5.0 out of 5 stars
• 7 reviews
4 repeat clients
8 years of experience
St. Louis, MO, 63146

“Julianna was so wonderful! She came for a meet and greet and followed all instructions for our dogs walk. She is so sweet, respectful, and you can tell she has a love for pets! We will definitely be using her again😊 thanks Julianna!”

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Breanne M.
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The median cost per walk for dog walking in Winchester is $20

Dog parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

Cynthia is amazing. Our dogs loved her. She stayed in contact and sent pics after every walk. I had nothing to worry about and will definitely hire again.

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Krista T.
Dog Walking
5.0 out of 5 stars

Lacy and Piper are always so excited to see Greg and Jane for walks. They are always on time and walk the dogs on the route I requested and give them lots of pets. I will definitely request Greg and Jane when I need dog sitting or the dogs walked.

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Mary Ann L.
Dog Walking
5.0 out of 5 stars

Jennifer was able to help me out on a last minute request to walk my dogs as I had to leave town. She walked both my dogs on a short notice and was great with them. Will book again!

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Nick D.
Dog Walking
5.0 out of 5 stars

Great skill in handling a large strong dog. Best thing is my dog looks forward to his walk with Sam.

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Jackie V.
Dog Walking
5.0 out of 5 stars

Very capable and very sweet. Riley loved her. We will definitely be booking with Lindsay many times. Rover has a winner with Lindsay.

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F. K.
Dog Walking
5.0 out of 5 stars

Lawton was awesome, I’m so impressed with how she cared for my pup on short notice! Will definitely be booking her again!

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Sarah S.
Dog Walking
5.0 out of 5 stars

Thomas is very responsive, thorough and provides feedback about whatever he is doing for Owen each visit. I appreciate all of his help while I am away. Thank you Thomas!

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Jane S.
Dog Walking
5.0 out of 5 stars

Charles was AWESOME! I’ll recommend him everytime.. booked walking for my dog and it was my first time ever hiring a dog walker or using Rovr. I love the updates and communication and photos of my pet. I felt at ease and comfortable. I knew my dog was in good hands. Great service!

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Mrs Nichole P.
Dog Walking
5.0 out of 5 stars

Shalini did a great job with walking our dog while I was out of town! Appreciated her communication and how thoroughly she prepared to ensure both she and our dog would be comfortable.

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Alice L.
Dog Walking
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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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How to book dog walking

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking.
  2. 2. Meet In Person

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Popular requests for dog walking - Winchester

Select a filter and find qualifying sitters offering dog walking.

Sitters in Winchester average 3
repeat dog walking clients

FAQs for Dog Walking - Winchester

Frequently asked questions about Rover

The average cost of Dog Walking in Winchester is $19 per walk as of October 2026. Most bookings cost between $13 and $28 per walk. On Rover, walkers 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 2,486 sitters on Rover offering Dog Walking across Winchester. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winchester. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Winchester after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

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 walker 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 .

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

  • 89% of walkers can help with special care needs
  • 94% can help with giving oral medications or injections
  • 97% 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 walker 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 walker 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 walker for longer stays or first-time bookings. Read our tips for your first .

walkers 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 walker.

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