Dog Walkers in Cheshire, MA

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

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Top rated Cheshire dog walkers

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
28 reviews
15 repeat clients
1 year of experience
Adams, MA, 01220

From Bella: “My most favorite visitor EVER!!! Every time Olivia come I get to run around the yard and go on walks. She makes me sit at every road crossing and as long as I’m good… which I am a good girl… I get a treat when I wait to cross! I get so excited to see my friend every day!”

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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 J.
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Caitlin J.
$23
total per walk
5.0 out of 5 stars
4 reviews
20 years of experience
Windsor, MA, 01270

About: I've loved animals forever and have cared for everything from a cockatiel to a chameleon, Great Pyrenees to Pekapoo. I currently have 1 Goldendoodle and 1 chocolate tabby cat in my home with fenced area and walking trails. I'm currently homeschooling my children at our 10+ acre home with fenced area and walking trails. We have a light schedule and are home more often than away. We currently walk our Goldendoodle daily and pet care is our love, in addition to our responsibility. I have a fenced area and multiple indoor secure areas where animals can get healthy time in a safe home without overstimulation. I have 1 Goldendoodle and 1 chocolate tabby cat who are the best of friends and are supportive to newcomers.

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

McKenna has been awesome! My dog loves her and I couldn’t be more happy with the level of care and support that she provides for my pup! A++ McKenna! Thanks so much!

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JC H.
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: 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: 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: Mariana F.
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Mariana F.
$18
total per walk
5.0 out of 5 stars
1 review
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: Leona O.
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Leona O.
$17
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: 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: 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: Skylar R.
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Skylar R.
Star Sitter
$34
total per walk
5.0 out of 5 stars
14 reviews
7 repeat clients
15 years of experience
North Adams, MA, 01247

About: Hello! My name is Skylar; I am 26 years old, my family has owned dogs my whole life, I own a dog and two cats! I currently work at a daytrain facility for dogs and am on my way to eventually becoming a dog trainer! I always provide the upmost care for animals. As an animal lover, I’m here to ensure that your family members stay happy and safe while you’re away! I currently work full time at a daytrain facility for dogs, typically in the afternoons - So I am available mostly in the mornings and evenings ( after 6 pm)! **FOR HOUSE SITTING REQUESTS BOOKED LESS THAN 7 DAYS IN ADVANCE** -> I do charge an expedited service fee of $20 a night on top of normal house sitting fee! I am able to provide walks if needed (or if there is no fenced in yard), as well as special diets and medications as needed! I do prefer using my own slip lead for safety reasons in the event there is no fenced in yard, however I am flexible with this!

Sitter Profile Image: Haley C.
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Haley C.
$23
total per walk
4 years of experience
Adams, MA, 01220

About: I’ve taken care for more than a handful of animals before! I have worked for two farms in my life so far. I have also always grown up with having dogs, cats, and even hamsters and Guinea pigs! I am a mom of 2 little ones but just recently moved so I am in between jobs and can work with you on times! I am available most days and a good portion of the day, as the kids go to daycare! I am a very good listener and fast learner. I love following a guideline and care so much about your animals! I can’t wait to meet your 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: 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.

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: 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: Nicole S.
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Nicole S.
$28
total per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
5 years of experience
North adams, MA, 01247

About: 5 years ago my family had gotten a puppy (jack Russell, beagle, terroir, Pitt bull mix). My puppy is a big baby, and is scared of everything. From flies to the wind. But he also can be a bit mean and over protective about his belongings. I was able to find ways around him being overly protective about his things. I was the main person to get up early to take him out in the mornings, throughout the day, and at night. We then a year later got his sister from a different litter from the same mom and dad. She is the complete opposite. She is a loving dog. She always wants to cuddle and loves to play and have all the attention to her. Since I was little I’ve always loved dogs. I love playing with them and walking with them. I’m a full time nanny but have a lot of free time on my hands while the kids are at school and their activities. I’m looking for some occasional work and maybe part time opportunities. I would always make sure the pet has food and water. Make sure the environment around them is safe. And make sure to attend their needs in any way that is needed.

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Over 7
pet parents in Cheshire have booked dog walking

Cheshire dog parents share their Rover experiences

1 / 1
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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The median cost per walk for dog walking in Cheshire is $25

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Sitters in Cheshire average 4
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Cheshire on Rover as of Jun 2026 was about $25 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Cheshire dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 142 dog walkers in Cheshire. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 86% of Cheshire dog walkers respond in under an hour.

Dog walkers in Cheshire have an average of 13 years of experience. Dog walkers with repeat customers have an average of 4 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Cheshire.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 142 dog walkers in Cheshire on Rover, so you’re sure to find the perfect match for your dog! In Cheshire, 100% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.