Dog Walking Wingdale

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Over 13
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Wingdale, 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: Kevin H.
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Kevin H.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
19 reviews
6 repeat clients
20 years of experience
Pawling, NY, 12564

Kevin is the best. The boys love him. Oliver wasnt feeling great, and Kevin took extra care of him by dropping him off at home, and taking Kiba back out.

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Anne T.
Sitter Profile Image: Casey S.
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Casey S.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
89 reviews
26 repeat clients
16 years of experience
Wingdale, NY, 12594

Casey did a great job showing up right on time and keeping me totally informed! She went above and beyond to make sure my dog was comfortable and taken care of.

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Eliot A.
Sitter Profile Image: Bianca W.
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Bianca W.
from
$25
per walk
1 repeat client
5 years of experience
Wappingers Falls, NY, 12590

About: Hi! I'm so glad you're here! I know how important it is to find someone you can completely trust with your pet and that's exactly the kind of care I strive to provide. Whether your pup needs a fun walk to burn off energy or they just want a friendly face while you're away, I'll make sure they feel safe, loved, and cared for every step of the way. I treat every pet as if they were my own, following their routine closely so they stay comfortable and stress-free. I have five years of experience with both my own and family members' dogs, giving me hands-on experience with daily walks, feeding, playtime, and providing lots of love and attention. You can expect dependable communication, plenty of photo updates, and personalized care based on your pet's unique personality and needs. I know every animal is different, and I take the time to earn their trust while making sure you have complete peace of mind. I currently work part-time, giving me flexibility for dog walks and drop-in visits throughout the week. I'd love the opportunity to meet you and your furry family member! Your pet's safety and well-being are always my top priorities. I understand that every pet has their own routine, personality, and needs, so I'll take the time to follow your care instructions carefully and make sure they feel comfortable during every visit. Whether we're out for a walk or spending time together at home, I'll provide a calm, caring, and dependable environment while treating your pet and your home with the utmost respect. My goal is to give you peace of mind, knowing your pet is in safe and caring hands. Here are the Services I offer and What to Expect: 30 Minute Dog Walks include a fun stroll around your neighborhood or a nearby trail to give your pup the exercise, fresh air, and mental stimulation they need during the day. 30 Minute Drop-Ins include potty breaks, feeding, playtime, and of course plenty of snuggles to keep your pet happy and comfortable while you’re away.

Sitter Profile Image: Becci S.
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Becci S.
from
$22
per walk
5.0 out of 5 stars
2 reviews
10 years of experience
Patterson, NY, 12563

Becci was wonderful would love to have her take care of our dogs again. She made sure she knew about all their needs and was so sweet to them

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Natalie F.
Sitter Profile Image: Stephen N.
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Stephen N.
Star Sitter
from
$50
per walk
5.0 out of 5 stars
36 reviews
13 repeat clients
25 years of experience
Beekman, NY, 12533

Steve does a great job with my dog Gus. He came and walked him while I was out of town for a few days. He has very great communication and I felt confident leaving Gus in his care. Highly recommend to others!

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Sean H.
Sitter Profile Image: Laudymarie S.
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Laudymarie S.
from
$25
per walk
28 years of experience
New Milford, CT, 06776

About: I’ve been surrounded by animals throughout my life and have cared for pets of all shapes, sizes, ages, and personalities, from small and shy to big, energetic, and outgoing. Because of that experience, I’m comfortable adapting my approach to each pet rather than expecting every animal to respond the same way. I’m confident caring for both small and large breeds, energetic puppies, adult pets, and seniors who may need a little extra patience and attention. I’m also comfortable administering medications and following specific feeding, exercise, or care instructions. I understand that shy or anxious pets may need time and space to build trust, while more outgoing pets might be ready for playtime the second I walk through the door! Most importantly, I treat every pet as if they were my own. I’ll pay attention to the little things, keep their routine as familiar as possible, and provide plenty of love, patience, and reassurance. I also know how important peace of mind is for pet parents, so you can expect reliable communication and updates while your furry family member is in my care. 🐾❤️ Pet care fits naturally into my daily routine, and I have the flexibility to dedicate plenty of time and attention to the pets in my care. I’m happy to work around each pet’s established schedule, whether that means morning or evening walks, regular potty breaks, feeding times, medication, playtime, or simply keeping them company. I understand how important consistency is for pets, especially when their favorite humans are away, so I make maintaining their normal routine a priority. Whether your pet needs lots of activity and attention or prefers a quieter day filled with naps and cuddles, I’m happy to adjust my schedule to what makes them happiest and most comfortable. 🐾❤️ When I’m caring for your pet in your home, I want them to feel like their routine hasn’t skipped a beat. I’ll follow your instructions closely, from meals, walks, potty breaks, and medications to favorite toys, sleeping spots, and all those little quirks that make your pet uniquely yours. 🐾 Having owned and cared for animals of all sizes, ages, and personalities throughout my life, I’m comfortable with the shy ones who need time to trust, the big personalities who want to play nonstop, and the seniors who just want some extra patience and love. I also know you’re trusting me with two things that mean a lot to you: your pet and your home. I’ll treat both with the same care and respect I’d want for my own. Expect plenty of love, attention, photos, and updates, because being away from your pet is much easier when you can actually see that happy face! ❤️🐶🐱

Sitter Profile Image: Jillian P.
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Jillian P.
from
$18
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
New Milford, CT, 06776

About: Growing up, I had a Lab and then a Boxer and two cats. I've also helped my aunt at the doggie daycare she runs out of her home where she often has more than 10 dogs at a time. Everything from a Great Pyrenees to German Shepherds to Doodles to Yorkies. And it's always so much fun! The care I'll give your pets will really depend on them and their needs. There's a very large unfenced grass area behind my apartment building that would be perfect for walks or play. And there are multiple parks in the area too we could explore. At yours, I'd keep whatever their normal routine is. Whether that's taking walks, throwing the ball or just sitting and chilling and scratching butts. Their butts of course! There's a very large unfenced grass area behind my apartment building that would be perfect for walks or for play. And there are multiple parks in the area too. At yours, it depends what you need. We could take walks, throw the ball or just sit and chill and scratch butts. Their butts of course!

Sitter Profile Image: Timothy D.
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Timothy D.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
5 reviews
3 repeat clients
20 years of experience
Arlington, NY, 12603

About: I have spent many years caring for dogs and I pride myself on building trust, providing excellent care, and treating every pet like they’re family. I have a very flexible schedule, allowing me to provide dependable care throughout the week. Animal care is a true passion of mine and I am committed to giving every pet the attention, exercise, and affection they deserve. I understand the importance of trusting someone with your pet and home. I am reliable, responsible, and committed to providing safe, professional care while keeping your pet comfortable and happy in their own home.

Sitter Profile Image: Manuel J.
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Manuel J.
from
$18
per walk
4.8 out of 5 stars
13 reviews
5 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

About: If you have an athletic or active dog, we are the hosts for you!!! Trips to parks (on and off leash), running the trails, and swimming in a Lake will happen every day. If your dog is less active, we can bring our activity level to where your dog is most happy and comfortable. I have a very open schedule. Usually I go to the park go with my family who enjoy the day doing things outside the house. If you have a last minute appointment or you need anything on the same day I do take them I have a very open schedule one works in the morning and the other one works in the afternoon so your pet will never be alone. I had pets before they pass away. We used to love our pets so much. We took CPR classes and emergency classes for pets just in case.

Sitter Profile Image: Don H.
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Don H.
from
$20
per walk
5.0 out of 5 stars
7 reviews
30 years of experience
Pawling, NY, 12564

About: My name is Don H. I am a professional pet sitter, dog walker and licensed dog trainer for 30+ years. I have been in the pet industry for many years, this is what I do full-time and love every minute of it. I care for all breeds of dogs and cats and also reptiles, fish, rodents, goats, horses I will e-mail/text or phone you updates and photos of your pet while you are away. I would love to help you out whether you need a pet/house sitter, dog training, dog walking, trail walks or your dog to be transported to Vet or Groomer. Your pet will be well cared for whether in your home or ours. I am a call way. Sincerely, Don My clients will give reference to how trustworthy and experienced I am when caring for pets in your home. I have respect for your property and even go the extra mile making sure your home is maintained and your pets are safe. I will take in your mail, water plants, take out your garbage/recyclables at no charge. Overnights include picking up after your pet inside and out. Why I love dog sitting I have been around all animals my whole life, I started my journey when I became a certified dog trainer. I also worked as a Kennel Manager for a medium-size kennel in Greenwich, CT. People tell me that I have great patience and calmness when working with difficult dogs. my goal is to help owners and their pet's to become one. I have over 25 years experience as a dog trainer and pet care provider. About my yard Yes i do have a backyard. Although it is not fenced in but I have tree barriers that keeps them safe. I also am close to a dog friendly park where all dogs are on leashes. I will not take a dog off leash when he/she is in my care. My experience administering medication Yes with my kennel experience, I am very comfortable administering medication. I am also comfortable administering shots for dogs and cats. I am a full time pet care provider and a dog walker and i have been training dogs of all breeds for the last 30 years. I give all my furry guest lots of play time and walks and all of our guest hang out with us we are cage free unless your owner wants your dog to sleep in one

Sitter Profile Image: Liliana N.
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Liliana N.
from
$16
per walk
7 years of experience
New Milford, CT, 06776

About: I take care of animals feeding them,cleaning after them cleaning litter boxes,socializing with them making sure they taking care of with extra love like they deserve I am working part time at shop rite two days a week so I am available anytime on my days off or after work I have open available I get my work scheduled every thursday two days advance before I planned anything for next week I would ask their owners how much food they should eat or if they are on restricted diet same for medications I would always ask them that before I do anything make sure I get the important details in first so I know what to do and what to expect ,I feed my cats Iam’s,play with them,hold them in my arms give them their morning pets and give their bedtime treats at 9:00 they already it and they are all lined up before I get in the kitchen .

Sitter Profile Image: Natalie B.
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Natalie B.
from
$30
per walk
5.0 out of 5 stars
9 reviews
2 repeat clients
30 years of experience
Brewster, NY, 10509

About: I am a lover of all animals big and small. I was blessed to own many species of pets while growing up. They taught me about responsibility, and gave me respect and appreciation for all living creatures. I have experience with many species: popular pets like dogs, cats, rabbits, and exotic pets such as ferrets, reptiles and fish. I am proud to say I am a NY state licensed Veterinary Technician with an animal medical background. I’m currently working full time but I like to make time to keep busy during the week with walks, boardings and sittings. I am very flexible. I have the ability to work from home and my husband is home during the day for additional care, when needed. I live in an apartment with a beautiful grassy yard for walking and a nice dog park onsite. I have a spare room for the dog to stay, if needed. I can also accommodate a crate trained dog. I can accommodate almost anything. Please let me know your requests and I will try my best to make it happen.

Sitter Profile Image: Jeffrey V.
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Jeffrey V.
from
$45
per walk
5.0 out of 5 stars
26 reviews
10 repeat clients
4 years of experience
New Fairfield, CT, 06812

Jeffrey was awesome. My pups loved him and he was totally able to deal with their less than perfect leash manners. He was reliable and friendly. I highly recommend him.

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Kristin R.
Sitter Profile Image: Kristen B.
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Kristen B.
from
$30
per walk
5.0 out of 5 stars
4 reviews
3 repeat clients
29 years of experience
Poughquag, NY, 12570

Great service. Wonderful with Aero and Diana.

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Godfrey M.
Sitter Profile Image: Samantha M.
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Samantha M.
from
$75
per walk
5.0 out of 5 stars
26 reviews
5 repeat clients
15 years of experience
Dover Plains, NY, 12522

About: Choosing a sitter is about more than just a check-in; it’s about finding a calm, capable environment where your pet feels truly understood. My background in healthcare naturally informs how I care for animals—I tend to be an observant caregiver, keeping a watchful eye on comfort levels and the small details that matter for a pet’s well-being. As a working-from-home mom, my days are rooted in a reliable routine. This allows me to provide the consistent, low-stress supervision that is so helpful for all animals who need a little extra help and those who require a patient, intuitive touch to feel at home. I have experience caring for a wide range of needs and species—from the high energy of puppies to the quiet companionship of seniors, the unique needs of rescues, and even farm friends like chickens. Whether it's keeping a medication schedule on track, assisting with mobility challenges, or simply providing a quiet space for a nervous soul to decompress, I focus on creating a safe, gentle environment where every animal in my care can truly relax. If for some reason (vacations/getaways) we are unavailable it will be marked on the calendar. I do my best to confirm my calendar and availability daily. Our front and back yard is fenced in and we are set back from the road. There is plenty of room to run and play. As for feeding; All dogs and/or cats will be fed separately. This includes treats.

Sitter Profile Image: Jamie B.
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Jamie B.
from
$25
per walk
25 years of experience
Pleasant valley, NY, 12569

About: I’ve loved animals for as long as I can remember. I rescued my first dog from the local humane society when I was 11, and that experience started a lifelong passion for caring for animals. Before becoming a nurse, I worked as a veterinary assistant for two local animal hospitals where I gained valuable hands-on experience with animal care and handling. I developed skills in basic training, puppy socialization, reading animal body language, medication administration, subcutaneous fluids, nail trimming, grooming, and bathing. I also volunteered for several years with a local dog rescue as a foster, helping provide temporary homes, structure, and love for dogs before their adoptions. Many needed socialization, basic training, and a calm environment to help them thrive. I later served as the rescue’s foster and event coordinator until 2020. Today I share my home with three of my own beloved dogs. One of our previous dogs had epilepsy and required frequent monitoring and medication, which gave me additional experience caring for pets with medical needs. In my free time I enjoy traveling, camping, hiking with my dogs, training with our Belgian Malinois, and watching my daughter ride her horse. Caring for animals has always been a true passion of mine, and I treat every pet as if they were my own. My goal is for you to have complete peace of mind knowing your pets are safe, loved, and well cared for while you’re away. I’m a nurse who works three 12-hour shifts each week, which gives me several days off to dedicate to caring for animals. I truly enjoy spending time with pets and making sure they feel comfortable, safe, and well cared for while their owners are away. My schedule is fairly flexible on my days off, and I’m happy to work with you to meet your pet’s individual needs and routine. Please check my calendar for availability and feel free to reach out with any specific requests. I will always do my best to accommodate and treat your animals with the same care and attention I would give my own. At this time, I’m unable to host dogs in my home, but I’m happy to care for them in the place they feel most comfortable—your home. I offer drop-in visits, dog walking, and extended daytime care depending on your pet’s needs. I understand how important it is to know your pets are safe, happy, and well cared for while you’re away. My goal is to provide dependable, personalized care in a calm and compassionate environment, treating your pets with the same attention and kindness I would give my own.

Sitter Profile Image: Denise S.
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Denise S.
from
$32
per walk
40 years of experience
Brewster, NY, 10509

About: I’ve been dog and cat sitting all my life. I also fostered a mid-size mixed terrier. I have two cats of my own. I love how all animals have amazing personalities! I can do dog walking, cat check ins with waste clean-up or over nights which ever you may need. I know how to administer meds to both cats and dogs. It is so important to have your furry loved ones pampered while you are away! I am retired so my availability is flexible. I also enjoy sending photos of your four legged loved one while you are away! I have also watched chickens, turtles, guinea pigs, snakes and iguanas. Looking forward to hearing from you! I am retired so I have a flexible schedule! I can go during the day or stay overnight at your home. Whichever you feel most comfortable with would work! When I come to your house, besides walking/feeding, I do waste cleanup as well. Of course, playing is a must! I will definitely send photos and videos so you know how your furry family member is feeling!

Sitter Profile Image: Harley Mae J.
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Harley Mae J.
from
$35
per walk
5.0 out of 5 stars
4 reviews
3 repeat clients
2 years of experience
Poughquag, NY, 12570

About: I took care of dogs around my neighborhood as a teen. For the past year I’ve been training a psychiatric service dog through my school. He lives with me full time! I am currently a student, so around my classes I have a lot of time to care for pets, especially on weekends. I love making the time to meet new animals and be outdoors. I have experience caring for dogs in my neighborhood and am always sure to leave a house as good or better than I found it.

Sitter Profile Image: Courtney C.
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Courtney C.
from
$30
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Brewster, NY, 10509

About: I've been surrounded by pets my whole life. Growing up, I cared for many cats and dogs. I don’t have any animals at the moment. However, I did care for my cat, Susan, and Siberian Husky, Luke, for 15+ years before they both crossed the rainbow bridge in 2019. I know the tender, loving care that’s required to take in an animal and I’m sensitive to the fact that these kittens & pups are your babies! Each dog/cat/pet has a different personality and set of needs based on their breed or lifestyle and I’m prepared to take on any challenge. I’ve had prior experience home/dog/cat sitting and my schedule is pretty flexible. My phone is on hand at all times and I’m more than willing to send you pics throughout our time together! Currently, I have a flexible schedule and am looking to care for cats and pups to fill my days with more furry friends. 🐱 🐶 When I had pets at home, I would care for them by taking them on walks and playing their favorite games. I installed an electric fence for my dog so he could run around and enjoy the outdoors when I couldn’t walk him.

Sitter Profile Image: Nikki C.
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Nikki C.
from
$32
per walk
5.0 out of 5 stars
7 reviews
13 years of experience
Brewster, NY, 10509

About: I have worked for a company where a strict protocol was needed to be followed regarding watching any animal. Between walks,feeding, medicine etc I would follow when caring for your pet along with having my own at home. My husband is also a trainer as well so we have experience with almost every breed and temperament ! I am home 24/7 so I would have all day home with your furry friend. I can do long term or short term and I am also very flexible and respond quick ! Not only Will I be giving your furry friend love and attention but I have two pups that love to run and play who will also be able too! They get along with everyone and are super playful!

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The median cost per walk for dog walking in Wingdale is $25

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Sitters in Wingdale average 3
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FAQs for Dog Walking - Wingdale

Frequently asked questions about Rover

The average cost for Dog Walking in Wingdale on Rover is $22.2 per walk (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

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

As of September 2026, there are 1,763 sitters on Rover offering Dog Walking across Wingdale. 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 Wingdale. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Wingdale.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Rover Guarantee , 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 Rover's Trust & Safety page .

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

  • 93% of walkers can help with special care needs
  • 97% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers 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 walker.

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