Dog Walking Cheshire

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

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Cheshire, Find top rated dog walking

Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Olivia S.
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Olivia S.
Star Sitter
$18
total per walk
5.0 out of 5 stars
33 reviews
15 repeat clients
1 year of experience
Adams, MA, 01220

Olivia is great with our new puppy! She is helping with training efforts and tiring her out during the day! I can trust that my puppy is in good hands while I’m not home!

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Nicole S.
Sitter Profile Image: Danielle P.
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Danielle P.
$17
total per walk
5.0 out of 5 stars
17 reviews
6 repeat clients
44 years of experience
Adams, MA, 01220

Danielle is the best dogwalker I've ever had. She's very attentive and knows each dogs special needs. They love her and go crazy when they hear her car in the driveway. I couldn't be happier!

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Mary W.
Sitter Profile Image: Caitlin H.
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Caitlin H.
$17
total per walk
5.0 out of 5 stars
17 reviews
3 repeat clients
4 years of experience
Pittsfield, MA, 01201

About: I acknowledge that routine is important with pets and therefore will mold my style to fit your pets norm. (This includes your rules for your pet, anything you are training them to do, and any medication). Before taking care of your pet I make sure I fully understand their daily routine to make sure their schedule isn’t thrown off. I have experience administrating medicine to pets. I also have experience giving baths to pets as long as their grooming supplies are supplied. Also I have taken care of pets for around 3 years and am very flexible as I want to make it as easier on you as possible. I am a teacher so I have all day to spend with your pup during summer months. Also during the school year, I get off in the late afternoon on Weekdays so I can be there to take care of your pup by early evening. I respect my clients space and I am also happy to take care of any additional things around the house (watering plants, bringing in mail, etc.) if asked.

Sitter Profile Image: Iris F.
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Iris F.
$17
total per walk
4.9 out of 5 stars
54 reviews
12 repeat clients
10 years of experience
North Adams, MA, 01247

Iris was pleasant to chat with. Georgia liked her and went into a calm mode with her soothing head pets. Iris handled Georgia well on the walk - maintaining control and kindness. I'm happy she'll be with Georgia sometimes.

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Tracy L.
Sitter Profile Image: Aura G.
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Aura G.
$28
total per walk
5.0 out of 5 stars
20 reviews
6 repeat clients
10 years of experience
Pittsfield, MA, 01201

About: Compassionate and experienced pet caregivers with a proven track record of providing top-notch care for dogs, including those with special needs. I am skilled in managing medical conditions such as convulsions and cancer, and I take a gentle, loving approach with every pet. I’m also well-versed in supervising curious eaters who love to snack on anything they can find! My husband, Nick, and I work as a team to ensure pets are cared for throughout the day. I’m home until 3 PM to handle mornings, walks, and plenty of daytime love and attention. Nick takes over in the evenings and overnight, so your pets continue to receive care, comfort, and companionship. Above all, we shower every furry friend with affection, making sure they feel safe, happy, and adored while in our home. As a dog walker, pet care is a regular part of my morning routine. I typically schedule dog walks Monday through Saturday, usually between , 8am-12pm. This allows me to provide a fun and energizing start to the day for the dogs in my care. I provide fun and safe dog walking services, giving your furry friend the exercise and attention they deserve. Here's how I care for your dog: - 30-minute to 1-hour walks tailored to your dog's individual needs and energy level - Safe and secure walks on a leash, with regular checks for comfort and happiness - Plenty of praise, affection, and treats to keep your dog happy and engaged - Regular updates and photos so you can stay connected with your dog's adventure Your dog's safety, comfort, and happiness are my top priority. I'll work with you to understand their unique needs and personality, ensuring a fun and enjoyable experience for both of us!

Sitter Profile Image: Zoey L.
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Zoey L.
$28
total per walk
10 years of experience
Adams, MA, 01220

About: I have pet/house sat multiple times over the past several years for friends and family, and have worked in animal shelters and a local doggy daycare, from small critters like guinea pigs and ferrets, cats, and even large dog breeds. I also have 2 years experience volunteering for a local shelter in socialization and vet transport, 3 years experience working for a doggy daycare and boarding facility, and I currently work part time for another local animal shelter. I am an experienced owner of dogs, cats, ferrets, chickens, guinea pigs, and more. I also have experience as a wedding dog handler, and would be happy to offer this service if requested so your furry companion can accompany you on your special day without any added stress. I currently work part time so I have lots of time to play with your pup, and hopefully can build savings towards a larger space to meet more people's needs! I am always looking to learn, grow, and provide better care for animals. Animal welfare is very important to me. At this point in time, due to the space I'm only able to accommodate smaller breeds that generally can get along with others. I do have a small fenced in yard, but I also have the bike trail and nearby hiking trails readily available, your dog will need to be on leash at all times when outside on walks/hikes, I do not provide "off-leash" trail experience as a safety precaution, thank you for your understanding! I am happy to provide pictures and updates of your pup whenever requested, please never be afraid to reach out!

Sitter Profile Image: Leona O.
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Leona O.
$20
total per walk
4.7 out of 5 stars
6 reviews
10 years of experience
North Adams, MA, 01247

About: I’ve taken care of dog of many sizes and health conditions, I have had a cat for 9ish years and have cared for friend and families dogs for years. I am a student, I am relatively free but lots of work to do! I like to go on walks already! I am able to be flexible. I know how to feed animals and care for them, can follow special instructions as I know they are important. As much as I would love to care for your fur baby at my home, I cannot.

Sitter Profile Image: Reymon B.
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Reymon B.
$23
total per walk
20 years of experience
Pittsfield, MA, 01201

About: Working in various Grooming/Training facilities. I'm currently working with Bumblebee Pet Care with 5 of my own clients. My conversations with the pets are amazing. I'm currently walking dogs 2 days out of the week looking for more to work with within the week. I have an open schedule and interested. I have separate spaces available for each animal. In my care at anytime, I will use provided equipment for transportation. Your pet safety is number one.

Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
$28
total per walk
5.0 out of 5 stars
382 reviews
149 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna came to walk my pup today and I came home to a happy and tired dog. McKenna is a very reliable, punctual, and caring dog sitter. She is extremely trustworthy and I recommend her wholeheartedly. My dog loves her!

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Diana K.
Sitter Profile Image: Maura A.
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Maura A.
$34
total per walk
5.0 out of 5 stars
3 reviews
30 years of experience
Adams, MA, 01220

About: Hi! I’m Maura, a high school English teacher who has lived and worked in the Berkshires for 19 years. I’ve spent my entire life caring for animals of all kinds, and my goal is simple: to provide safe, personalized care so you can enjoy your time away without worrying about your pets. I offer dog walking, drop-in visits, house sitting, overnight pet care, and small farm sitting throughout the Berkshires. Whether you need someone to check on a new puppy, care for a senior pet, or manage a small farm while you’re away, I’d love to help. I have experience caring for dogs, cats, rabbits, ferrets, hamsters, gerbils, rats, large aquariums, horses, cows, goats, and pigs. In addition to caring for my own animals, I have experience managing an equine boarding facility with 19 horses on the property and am comfortable handling a variety of animal personalities, energy levels, and care needs. I am experienced with: • Puppies and kittens • Senior pets • Oral medication administration • Basic trick training and potty training • High-energy dogs • Shy or anxious animals • Horses and livestock requiring daily care routines I also offer red light therapy sessions for pets, both small and large, upon request. Coming soon: private in-home boarding! I am currently creating a private pet guest house on my property that opens directly into a fully fenced backyard. My goal is to provide a low-stress alternative to traditional kennels by boarding only one pet family at a time. This allows your pets to receive individualized attention in a quiet, secure environment without the stress of sharing space with unfamiliar animals. If this is something you’d be interested in, feel free to reach out for details. I know firsthand how stressful it can be to leave beloved pets behind when traveling. That’s why I prioritize communication, reliability, and personalized care. I provide regular photo updates and am always happy to check in while you’re away so you can feel confident that your pets are safe, comfortable, and well cared for. Whether you’re visiting the Berkshires for a weekend, heading out for a day of skiing or sightseeing, or leaving town for a longer trip, I’d love the opportunity to care for your pets as if they were my own. Please feel free to reach out with any questions about services, availability, or your pet’s specific needs. I look forward to meeting you and your animals! I’m always running errands for my pets, spending time with my pets, or I’m at the barn with my horse. Taking care of the needs of my own pets is one of my top priorities, and I can easily work your furry friend into my schedule! It’s important that we discuss your specific expectations and needs as a pet owner/parent to ensure that you get the best care! Every pet owner and pet is different and I want to tailor my approach to what your pet is used to and comfortable with.

Sitter Profile Image: Connie R.
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Connie R.
$17
total per walk
1 repeat client
30 years of experience
Pittsfield, MA, 01201

About: I have been taking care of animals since I lived at home when I was younger with my parents I was very responsible I love talking to my animals I love taking time with them, making sure that they feel loved And that they felt like they were part of the family! I do work full-time, but during the day, I am able to have a flexible schedule and care to animals. I have more availability during the weekends. I care for pets in my home I make sure that my home is pet proof specially, since I have a dog of my own I make sure that everything that would be unsafe to my dog is put away if areas need to be gated off and make sure that they’re gated off and they make sure that she has all the food that she needs healthy foods and water to drink. If I was caring for a pet and someone else’s home, I would follow instructions that they leave for me and I would also make sure that their pet was comfortable and safe

Sitter Profile Image: James S.
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James S.
$34
total per walk
5.0 out of 5 stars
8 reviews
10 years of experience
Williamstown, MA, 01267

About: I bring a unique level of structure, energy, and reliability to pet care through my experience as a college coach. My daily work revolves around building routines, paying attention to small details, and making sure individuals are supported and performing at their best — and I carry that same approach into caring for dogs. I am highly dependable and organized, so you can trust that your dog’s schedule, feeding routine, and exercise needs will be handled consistently. I also bring an active lifestyle, which is great for dogs that need engaging walks, playtime, and attention. What sets me apart is the level of care and awareness I provide. I pay close attention to behavior, energy levels, and any changes, and I prioritize clear communication so you always feel confident while you are away. My goal is to make sure your dog feels comfortable, safe, and well cared for at all times My schedule is currently wide open following the end of the swim season, which gives me plenty of flexibility for walks, drop-ins, and overnight care throughout the week and weekends. I understand how important it is to trust someone with your dog. I create a safe, comfortable environment where your pet feels secure and cared for at all times. I pay close attention to their needs, keep a watchful eye during walks, and always make sure you are updated so you can relax knowing they are in good hands.

Sitter Profile Image: Christina D.
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Christina D.
$34
total per walk
5.0 out of 5 stars
5 reviews
20 years of experience
Pittsfield, MA, 01201

About: My experience in pet care began during my childhood on my grandparents’ farm, where I was surrounded by a wide variety of animals every day. From an early age, I learned the importance of responsibility, compassion, and attentive care. I gained hands-on experience feeding, grooming, and nurturing animals of all kinds—including dogs, cats, livestock, and small animals—each with their own unique needs and personalities. More than just daily routines, I developed strong, loving bonds with the animals I cared for, treating them as family. That foundation shaped my deep understanding of animal behavior and my commitment to providing patient, personalized, and reliable care for every pet I work with. I bring a deep love and understanding of dogs of all ages, sizes, and personalities. From playful pups to sweet seniors, I tailor each walk to fit their needs. I prioritize safety, communication, and fun—always engaging with your dog and even teaching basic cues like sit, stay, and wait during our adventures. I’m passionate about nature and I believe dogs thrive when they can safely explore their environment —sniffing the breeze, feeling the grass under their paws, and soaking up the world around them. I’m dependable, energetic, and treat every dog like my own. Whether it’s a gentle stroll or a playful outing, your pup will be in great hands and have a tail-wagging good time! Dog walking fits perfectly into my current routine. I’m a part-time healthcare worker with a consistent schedule, working from 8 a.m. to 1 p.m. on Monday, Tuesday, Thursday, and Friday. Outside of those hours, I have a flexible schedule and plenty of availability and plenty of time to dedicate to your pup. I truly enjoy incorporating walks into my day—they keep me active, bring me joy, and let me connect with more wonderful dogs. Your dog will receive dependable, loving care from someone who’s already made this a part of daily life. Safety, trust, and a positive environment are at the heart of every walk I take. I prioritize clean, open, and dog-friendly spaces—like the Rail-Trail, local parks, and secure walking paths—where pups can enjoy fresh air and nature safely. I always use leash control, stay highly observant of their behavior, and make sure every walk is calm, comfortable, and secure. Whether we’re exploring a quiet trail or playing at a safe dog park, your dog’s well-being is my top priority. You can trust that your pup is in caring, capable, and experienced hands every step of the way.

Sitter Profile Image: Aubrey H.
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Aubrey H.
$28
total per walk
5.0 out of 5 stars
11 reviews
8 repeat clients
21 years of experience
North Adams, MA, 01247

About: I've taken care of animals all shapes and sizes since I can remember. Growing up my only job was to make sure my fur babies were fed and loved unconditionally. I would go to a friend of the family and help her with her pit bull and (several) greyhounds. I've worked at kennels from a young age and have had my own share of birds, mice, fish, hamsters, Guinea pigs, and chinchillas as well as dogs and cats. The home has only been without pets for around 7 months now and I would love to dedicate some of my time to people who need genuine love and care for their fur babies! I do not have a job, I am around all of the time! I can be there any time day or night! You name it. I do not have a fenced in yard, however all of the neighborhood doggies are very very friendly. I have a decent sized yard and live next to multiple fields and grassy areas.

Sitter Profile Image: Dana G.
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Dana G.
$34
total per walk
5.0 out of 5 stars
40 reviews
11 repeat clients
20 years of experience
PITTSFIELD, MA, 01201

Dana- thank you so much! You came in clutch for us tonight! Thank you thank you! Tippy already can’t wait until next time!

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Brittny L.
Sitter Profile Image: Mariana F.
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Mariana F.
$18
total per walk
5.0 out of 5 stars
2 reviews
10 years of experience
North adams, MA, 01247

About: ive had a couple of dog growing up in my childhood a sweet old black lab and a super crazy dingo.. in my free time after school and during summer i used to walk them, no amount of walking could satisfy my dingo.. id have her pull my bike to get all her energy out since we didnt have any closed in areas she could run off in.. ( i dont do this anymore! i realize its not very safe! she absolutely loved it for sure though) i love pups big and small old and energetic theyre all very unique and id love some new friends to get me out of the house. id ask you beforehand of course if youd be okay with them swimming, theres a pond i can bring them to after walking to cool off at. our backyard is fenced! i have two cats, so id like to know how your dog reacts around small creatures, if they cant be in contact i can always but them into a room while the dog is over. most likely theyd be outside! lots of shade and id keep em well hydrated and happy :3 i currently have been on a job hunt since what feels like forever, my schedule is very. very open.. since i dont have a car, drop off would be ideal, if your close enough to walk to i can do that too! weekends are the only time id be able to pick up your pooch my cats get their waters filled and cleaned almost daily, lots of love of course and are very spoiled. i dont have any dogs at the moment, so of course id love to chat about what youd expect and need for your lovely pup! im good with communication and friendly, special needs id be extra attentive to. im very good at remembering small things, though id still write em down incase!

Sitter Profile Image: Ivan O.
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Ivan O.
$23
total per walk
5.0 out of 5 stars
6 reviews
20 years of experience
New Lebanon, NY, 12125

About: I have raised 3 dogs from puppy through adulthood with great love and attention. Looking forward to helping others with their beloved pets! Our home is heaven for any dog or cat. My wife and I both work from home so we're always around to provide attention, playtime, walks, feedings, grooming, etc. Our dog Moreno is super friendly and agreeable with other dogs and cats. Our son loves them too! Multiple walks a day, leashed or off depending on the dog. Gated porch for fresh air time. Dog beds, toys, lots of space for people and pets!

Sitter Profile Image: Melanie D.
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Melanie D.
$28
total per walk
20 years of experience
Dalton, MA, 01226

About: I grew up with dogs my whole life. My parents also run a dog sitting business on cape cod and I help out there when I can! I am also fully insured! I’m a current second grade teacher, so I’m completely free on the weekends and the summer months, as well as school vacations to take care of your furry friends! I will love your dog like my own! I’m a diligent, reliable and clean person that will leave your home and dog happier than I found it. I am also fully insured!

Sitter Profile Image: Emily P.
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Emily P.
$22
total per walk
5.0 out of 5 stars
4 reviews
1 repeat client
35 years of experience
Pittsfield, MA, 01201

About: Pet/animal care is part of my soul and my heart. From puppies to seniors I shower them with love, patience and dignity. I love it! I have the time and the space for your sweet fur babies on the weekends and after work. If I can help you, please let me! I will always adapt to the needs of each animal. If I can accommodate any needs, cautions or desires, It will be my pleasure! :)

Sitter Profile Image: Jessie L.
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Jessie L.
$39
total per walk
5.0 out of 5 stars
8 reviews
4 repeat clients
17 years of experience
Adams, MA, 01220

About: My name is Jess! Thank you for stopping by! ☺️ I’m 30 and work from home in Adams, MA. I have a fairly flexible schedule and am a classic Berkshire native. I have been a pet owner and lover my entire life! My boyfriend and I currently have two cats, Binx & Titan. Who are the loves of our lives. My family has always been pet lovers! We’ve recently lost our two havanese pups. We were pervious owners of a chocolate lab and a poodle mix. I’ve spent my life around different breads of dogs, big and small. As well as lots of cats! I will care for your pets just as you would and am happy to provide in home care in their own space to provide the best comfort. I am confident in handling all types of breds and needs of pets. I’ve been an experienced dog sitter for over 15 years! I started doing this when I was a teenager and never stopped. I love caring for animals. Please consider me for your pets next walk, meal, or sleepover! I currently work from home full time! I prefer to chat to see if the conditions work for both myself and the pets! Always open to questions/concerns/inquiries! My message box is always open. I prefer to care for pets just as you would! I love to understand their current routine and try to keep things as normal as possible for them to prevent anxieties.

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The median cost per walk for dog walking in Cheshire is $22

Dog parents share their Rover experiences - Cheshire

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5.0 out of 5 stars

Morgan was very patient with Maple as this was their first time meeting and Maple was a bit anxious to go for a walk with a new person.

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Caley V.
Dog Walking
5.0 out of 5 stars

Morgan is excellent with our pooch. She immediately put our rescue dog, who is usually wary of new people, at ease. Thanks Morgan!

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Liezl I.
Dog Walking
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Sitters in Cheshire average 3
repeat dog walking clients

FAQs for Dog Walking - Cheshire

Frequently asked questions about Rover

As of July 2026, there are 692 sitters on Rover offering Dog Walking across Cheshire. 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 Cheshire. 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 Cheshire.

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 Cheshire. On Rover:

  • 93% of walkers can help with special care needs
  • 98% 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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