Dog Walkers in Cheshire, MA

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Top rated Cheshire dog walkers

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Sitter Profile Image: Emma K.
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Emma K.
Star Sitter
from
$15
per walk
5 out of 5.0 stars
29 reviews
15 repeat clients
8 years of experience
Pittsfield, MA, 01201

Emma is walking my dog several times a week & she is wonderful! My dog Gigi is usually timid with new people but went to Emma immediately & stood up on her for kisses & pets, so Emma is obviously a dog person. She’s also very reliable & I highly recommend!

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Jennifer L.
Sitter Profile Image: Danielle P.
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Danielle P.
from
$15
per walk
5 out of 5.0 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: Olivia S.
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Olivia S.
from
$16
per walk
5 out of 5.0 stars
13 reviews
6 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: McKenna P.
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McKenna P.
Star Sitter
from
$25
per walk
5 out of 5.0 stars
342 reviews
135 repeat clients
8 years of experience
Lenox, MA, 01240

You can tell McKenna is a big animal & dog lover. She was incredibly sweet & gentle during our meet & greet. She asked all the right questions and our pups felt instantly comfortable around her. We’re glad to establish a relationship with someone we can trust AND with someone who goes above & beyond during her visits. Thank you McKenna, we’ll be booking you again soon!

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Graham S.
Sitter Profile Image: Iris F.
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Iris F.
Star Sitter
from
$25
per walk
5 out of 4.9 stars
51 reviews
11 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: Caitlin H.
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Caitlin H.
from
$15
per walk
5 out of 5.0 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: Amanda S.
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Amanda S.
Star Sitter
from
$35
per walk
5 out of 5.0 stars
35 reviews
15 repeat clients
25 years of experience
Pittsfield, MA, 01201

Thanks for taking great care of our dogs!! Loved the pictures and great communication.

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Maria V.
Sitter Profile Image: Madison M.
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Madison M.
from
$16
per walk
17 years of experience
Pittsfield, MA, 01201

About: I have owned a dog since I was 3 years old, I grew up with her and she is the greatest blessing! I truly believe dogs have many skills and a way of communicating that no one else can while showing you the most live and affection! I am available anytime Monday-Friday and can be scheduled for availability on weekends if needed! I am very flexible and willing to work with you and your needs! I show any puppy love and compassion. I take time to allow them to get comfortable and get to know me. I do not force dogs to get along with someone they do not like

Sitter Profile Image: Christina D.
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Christina D.
from
$25
per walk
5 out of 5.0 stars
4 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: Jason R.
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Jason R.
from
$20
per walk
25 years of experience
Pittsfield, MA, 01201

About: I've had 5 dogs in 25 years. My 7yr old rescue black lab mix Luna is my current forever pup. She's up for anything & everything. I have an open schedule since retirement. I am looking forward to spending more time outdoors and taking care of other dogs and their owners. Our back yard is fenced in. We have large dog crate if needed. There is a park nearby that we bring our dog to often. I can travel in my vehicle with dogs

Sitter Profile Image: Connie R.
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Connie R.
from
$15
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: Aubrey H.
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Aubrey H.
from
$25
per walk
5 out of 5.0 stars
10 reviews
6 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: Aura G.
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Aura G.
from
$25
per walk
10 years of experience
Pittsfield, MA, 01201

About: Compassionate and experienced pet caregiver with a proven track record of providing top-notch care for dogs with special needs. Skilled in managing medical conditions such as convulsions and cancer, with a gentle and loving approach. Also well-versed in supervising curious eaters who love to snack on anything they can find! Above all, I shower my furry friends with love, attention, and affection, ensuring they feel safe, happy, and adored in my care. 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: Rita M.
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Rita M.
from
$20
per walk
18 years of experience
North Adams, MA, 01247

About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently working various part time jobs, so i will need at least two weeks notice for a majority of the services i provide. i will try my best to arrange my schedule for your convenience! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

Sitter Profile Image: Daniella S.
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Daniella S.
from
$20
per walk
5 out of 5.0 stars
7 reviews
4 repeat clients
7 years of experience
Pittsfield, MA, 01201

She was pleasant and communicated when needed. We appreciated her help and will reach out to her again in the future.

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Angie H.
Sitter Profile Image: Lori M.
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Lori M.
from
$30
per walk
5 out of 5.0 stars
7 reviews
2 repeat clients
50 years of experience
Hinsdale, MA, 01235

I had been very anxious about going away for a long weekend with my family since we booked our stay a few weeks ago. Our boy Nicholas is now a senior guy and the last couple of years I've been too apprehensive about being away from him. I knew if I were to go he would need to remain in-home for his comfort. We decided to give Rover a try and after the very first visit Lori eased our worries immediately. She is so kind, thorough and provided as much love to him as we would if we were home. After each visit she sent wonderful videos of our boy enjoying his walks and offered reports on how he was on his walks and how he was eating/drinking. This was THE most wonderful service and cannot thank Lori enough!

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Michael O.
Sitter Profile Image: Mariana F.
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Mariana F.
from
$16
per walk
5 out of 5.0 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: Skylar R.
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Skylar R.
from
$25
per walk
15 years of experience
Dalton, MA, 01226

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 am relatively flexible as I work around my jobs schedule but I always provide the upmost care for animals. As a dog lover, I’m here to ensure that your family members stay happy and safe while you’re away! I currently work part time at a daytrain facility for dogs, typically in the afternoons - So I am available mostly in the mornings and evenings ( after 6 pm)! 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!

Sitter Profile Image: Bella G.
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Bella G.
from
$30
per walk
5 out of 5.0 stars
13 reviews
2 repeat clients
10 years of experience
lanesborough, MA, 01237

About: I have my own dog walking/Pet Sitter business called “Canine in motion” On facebook and instagram. I’m super excited to have new clients reach out to me that need a dog walker/pet sitter. I’ve worked at an animal shelter, a doggy day care and I also volunteer at a nearby animal shelter to help walk dogs weekly. Through those experiences i’ve learned so much about different dog breeds and other small animals. I’ll treat your dog like my very own! I’m currently working part-time, so I’ll have plenty of time to play with your pup! I’m available for pet sitting/dog walking Monday-Friday. My weekends are also free. Why should I look after your dog while you're on vacation or unable to look after them? I give genuine love and passion to dogs. I understand their needs, both physical and emotional, and i’m dedicated to providing them with the utmost care and attention. My patience and attentiveness allow me to anticipate their needs and respond accordingly, ensuring their comfort and well-being. I have a keen eye for detail, noticing subtle cues and behaviors that may indicate their mood or health. I’m responsible, I follow instructions diligently, whether it's regarding feeding, exercise, or medication. My calm and nurturing presence creates a safe and secure environment, allowing dogs to feel at ease in my care. With me, dogs will find a trustworthy and compassionate companion, someone who will go above and beyond to ensure their happiness and safety.

Sitter Profile Image: Jacob B.
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Jacob B.
from
$35
per walk
20 years of experience
Lanesborough, MA, 01237

About: Hello, my name is Jake. I am a very outgoing guy with lots of energy which makes me the perfect candidate to play with and care for your pets. I’ve had pets my entire life and am very caring with animals. I will make sure that your pets are well maintained and cared for 100% of the time. I can follow instructions very well. I will also make sure that the experience for your pet/pets is as wonderful as I can possibly make it. If there is anything else I can do to make your experience with me as your pet care taker any better I will be right on top of that wholeheartedly. Thank you for taking the time to read my introduction. I look forward to working with you!

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Sitter Profile Image: Emma K.
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Sitter Profile Image: Emma K.
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Emma K.
Star Sitter

Unleashing Quality Pet Care
Pittsfield, MA, 01201
9.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
29 reviews
15 repeat clients
Profile image

Emma is walking my dog several times a week & she is wonderful! My dog Gigi is usually timid with new people but went to Emma immediately & stood up on her for kisses & pets, so Emma is obviously a dog person. She’s also very reliable & I highly recommend!

Availability updated 18 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Danielle P.
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Sitter Profile Image: Danielle P.
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Danielle P.
Rover 101

DOES ROVER NEED EXERCISE?
Adams, MA, 01220
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
17 reviews
6 repeat clients
Profile image

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!

Availability updated 72 days ago
Sitter Profile Image: Olivia S.
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Sitter Profile Image: Olivia S.
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Olivia S.

Former Vet Assistant!
Adams, MA, 01220
4.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
13 reviews
6 repeat clients
Profile image

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!

Availability updated today
Sitter Profile Image: McKenna P.
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Sitter Profile Image: McKenna P.
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McKenna P.
Rover 101
Star Sitter

Avid Dog Lover and Sitter
Lenox, MA, 01240
12.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per walk
5 out of 5.0 stars
342 reviews
135 repeat clients
Profile image

You can tell McKenna is a big animal & dog lover. She was incredibly sweet & gentle during our meet & greet. She asked all the right questions and our pups felt instantly comfortable around her. We’re glad to establish a relationship with someone we can trust AND with someone who goes above & beyond during her visits. Thank you McKenna, we’ll be booking you again soon!

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Iris F.
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Sitter Profile Image: Iris F.
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Iris F.
Star Sitter

Vet Tech student who loves Animals
North Adams, MA, 01247
10.2 mi. away
Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 4.9 stars
51 reviews
11 repeat clients
Profile image

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.

Availability updated 42 days ago
Sitter Profile Image: Caitlin H.
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Sitter Profile Image: Caitlin H.
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Caitlin H.

Flexiblity to meet your pet needs
Pittsfield, MA, 01201
9.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
17 reviews
3 repeat clients

Caitlin is wonderful. She has been taking care of our very shy rescue for over a year any time we go away. Caitlin has watched the pup for anywhere from a night to up to 3 weeks. She is wonderful with our dog and also extremely reliable and responsive. I trust her to take care of my fur baby and also to hold down the fort at our house. We're lucky to have Caitlin around.

Availability updated 14 days ago
Sitter Profile Image: Amanda S.
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Sitter Profile Image: Amanda S.
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Amanda S.
Star Sitter

Dogs, Cats and Chicks!
Pittsfield, MA, 01201
9.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per walk
5 out of 5.0 stars
35 reviews
15 repeat clients
Profile image

Thanks for taking great care of our dogs!! Loved the pictures and great communication.

Availability updated 4 days ago
Sitter Profile Image: Madison M.
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Sitter Profile Image: Madison M.
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Madison M.

Home is where the paws are!
Pittsfield, MA, 01201
8.2 mi. away
Drop-In Visits, Dog Walking
from
$16
per walk
17 years of experience

About: I have owned a dog since I was 3 years old, I grew up with her and she is the greatest blessing! I truly believe dogs have many skills and a way of communicating that no one else can while showing you the most live and affection! I am available anytime Monday-Friday and can be scheduled for availability on weekends if needed! I am very flexible and willing to work with you and your needs! I show any puppy love and compassion. I take time to allow them to get comfortable and get to know me. I do not force dogs to get along with someone they do not like

Availability updated 6 days ago
Sitter Profile Image: Christina D.
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Sitter Profile Image: Christina D.
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Christina D.

Zen & Zoomies Dog Walks
Pittsfield, MA, 01201
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
4 reviews

Christina is an amazing, delightful and joyful person who carries that over to the pets she takes care of. She is excellent with dogs and always makes sure they have a great, fun and attentive experience with her, as if they were her own! I highly recommend Christina, she is very dependable, safe, and incredibly caring, If you are looking for a great individual to walk your dog who has a lot of fun doing it, then Christina is the person for the job!

Availability updated 3 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jason R.
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Sitter Profile Image: Jason R.
Verified Enhanced Background Check

Jason R.

Retired Public Safety Professional
Pittsfield, MA, 01201
7.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
2 reviews

I know Jason to be a responsible & loving dog owner. He has taken the time to raise & train his own dog & spends the necessary time to play & interact with his dog. He walks his dog regularly. He is an honest & trustworthy person who would only treat others’ pets as he would his own. This would not be a chore or a job for him, it would be a privilege to assist others in pet caregiving.

Availability updated 9 days ago
Sitter Profile Image: Connie R.
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Sitter Profile Image: Connie R.
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Connie R.

Caring for a pet is a blessing! I
Pittsfield, MA, 01201
8.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per walk
1 repeat client

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

Availability updated 7 months ago
Sitter Profile Image: Aubrey H.
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Sitter Profile Image: Aubrey H.
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Aubrey H.

Ready to Love your Fur Babies♥️
North Adams, MA, 01247
9.3 mi. away
Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
10 reviews
6 repeat clients

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.

Availability updated over 1 year ago
Sitter Profile Image: Aura G.
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Sitter Profile Image: Aura G.
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Aura G.

Love, Care and Belly rubs!
Pittsfield, MA, 01201
7.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per walk
10 years of experience

About: Compassionate and experienced pet caregiver with a proven track record of providing top-notch care for dogs with special needs. Skilled in managing medical conditions such as convulsions and cancer, with a gentle and loving approach. Also well-versed in supervising curious eaters who love to snack on anything they can find! Above all, I shower my furry friends with love, attention, and affection, ensuring they feel safe, happy, and adored in my care. 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!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Rita M.
Verified Enhanced Background Check
Sitter Profile Image: Rita M.
Verified Enhanced Background Check

Rita M.

i’ve always loved animals! ❤️
North Adams, MA, 01247
10.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
18 years of experience

About: I’ve interned at my local vet clinic for two years now and have recently moved to a paid position as an assistant! through this internship i have not only learned substantial knowledge regarding pet care, such as how to most effectively administer medications, but also discovered my love for pet sitting, as i have become one of the veterinarian’s permanent pet sitter! i also plan to go to vet school after i earn my bachelors degree! i am currently working various part time jobs, so i will need at least two weeks notice for a majority of the services i provide. i will try my best to arrange my schedule for your convenience! i’ll treat your furry family like my own! i come with treats ready (with permission of course) and never leave without a game of fetch or whatever else your babies might enjoy! they’ll definitely be the highlight of my day, so i’ll try to be there’s too!

Availability updated 16 days ago
Sitter Profile Image: Daniella S.
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Sitter Profile Image: Daniella S.
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Daniella S.

Passionate animal lover!
Pittsfield, MA, 01201
9.5 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
7 reviews
4 repeat clients
Profile image

She was pleasant and communicated when needed. We appreciated her help and will reach out to her again in the future.

Availability updated 27 days ago
Sitter Profile Image: Lori M.
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Sitter Profile Image: Lori M.
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Lori M.

My pup is my best pal!
Hinsdale, MA, 01235
8.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per walk
5 out of 5.0 stars
7 reviews
2 repeat clients
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I had been very anxious about going away for a long weekend with my family since we booked our stay a few weeks ago. Our boy Nicholas is now a senior guy and the last couple of years I've been too apprehensive about being away from him. I knew if I were to go he would need to remain in-home for his comfort. We decided to give Rover a try and after the very first visit Lori eased our worries immediately. She is so kind, thorough and provided as much love to him as we would if we were home. After each visit she sent wonderful videos of our boy enjoying his walks and offered reports on how he was on his walks and how he was eating/drinking. This was THE most wonderful service and cannot thank Lori enough!

Availability updated 7 days ago
Sitter Profile Image: Mariana F.
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Sitter Profile Image: Mariana F.
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Mariana F.

love all creatures fuzzy and cute!
North adams, MA, 01247
9.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per walk
5 out of 5.0 stars
1 review

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!

Availability updated 41 days ago
Sitter Profile Image: Skylar R.
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Sitter Profile Image: Skylar R.
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Skylar R.

All around animal lover right here!
Dalton, MA, 01226
8.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
15 years of experience

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 am relatively flexible as I work around my jobs schedule but I always provide the upmost care for animals. As a dog lover, I’m here to ensure that your family members stay happy and safe while you’re away! I currently work part time at a daytrain facility for dogs, typically in the afternoons - So I am available mostly in the mornings and evenings ( after 6 pm)! 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!

Availability updated 3 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Bella G.
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Sitter Profile Image: Bella G.
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Bella G.
Rover 101

Huge animal lover
lanesborough, MA, 01237
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per walk
5 out of 5.0 stars
13 reviews
2 repeat clients

Bella is great friend, and really care for animals. I’ve seen so first hand with her dog and mine. I would say one person I would trust the most with my animals if I was every way or something would be Bella. She just a all around good person and knows how to brighten the day. I’ve also never seen anyone else take care of a animal like she does. Great person with great personality and caring.

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jacob B.
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Sitter Profile Image: Jacob B.
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Jacob B.

Excited to care for your pets!
Lanesborough, MA, 01237
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per walk
20 years of experience

About: Hello, my name is Jake. I am a very outgoing guy with lots of energy which makes me the perfect candidate to play with and care for your pets. I’ve had pets my entire life and am very caring with animals. I will make sure that your pets are well maintained and cared for 100% of the time. I can follow instructions very well. I will also make sure that the experience for your pet/pets is as wonderful as I can possibly make it. If there is anything else I can do to make your experience with me as your pet care taker any better I will be right on top of that wholeheartedly. Thank you for taking the time to read my introduction. I look forward to working with you!

Availability updated 62 days ago

Over 4 pet parents in Cheshire have booked dog walking

How Rover works

  1. 1. Search

    Read verified reviews and choose a dog walker who’s a great match for you and your dog
  2. 2. Meet & Greet

    Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your dog walker has to cancel, we’ll work with you to find a new walker.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Cheshire average 4 repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover