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Find Trusted Dog Sitters Near Me in Cheshire, MA

Explore background-checked dog sitters in Cheshire, MA and find loving care for your furry friend. Compare rates and reviews to find the best fit.

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Kelly D.'s Photo

Kelly D.

Cheshire, MA

from
$25/hr
Pet transportation
pet walking
pet sitting
I am a 48-year-old mother, wife, and grandma to my sweet granddaughter. I have had pets my whole life. Growing up, my dad had all kinds of small pets, including birds, fish, rodents, cats, dogs, and even reptiles, which we would help care for. I have 4 years of experience working with horses and donkeys as a handler, as well as...
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Ava-lena S.'s Photo

Dog Sitter/Walker

Pittsfield, MA

5.0(0)
from
$15/hr
8 years experience·
Hired by 1 families in your area
Pet sitting
pet walking
daily feeding
boarding
administration of medicine
I have been pet-sitting for about 7 years. I have cared for puppies, full-grown dogs of all sizes, and cats. I love dogs; I had one of my own!
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Samantha W.'s Photo

Pet Care

Lanesborough, MA

5.0(1)
from
$30/hr
10 years experience·
Hired by 7 families in your area
Pet walking
dog training
pet sitting
boarding
administration of medicine
+ 1 more
Hey Everyone! I have been working with animals (pet sitting and house sitting) for 10 years. I started my animal care journey volunteering at the Animal Shelter after graduating high school in 2007; during the 3 years of work there I realized my extreme passion for animals. I then started fostering for a New York rescue group,...

Pat B. says "I was in a hotel Pittsfield for a few nights, and asked Samantha to stay with my dog while I went out to dinner with friends. (I was concerned that my dog...

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Eileen Z.'s Photo

Adams, MA

from
$18/hr
5 years experience
Pet walking
pet sitting
I have worked with families for years. From babysitting, house sitting, pet sitting. I love every minute that I get to spend with dogs and all other pets.
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Whitney S.'s Photo

Pet Sitter And Visitor

Adams, MA

from
$15/hr
I am an animal lover and grew up in a house filled with dogs, cats, birds and bunnies. After college, I lived and worked on my aunt's goat farm and got to know horses, cows and goats (of course). I would be happy to walk your dog while you're at work or pet sit for you while out of town.
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Alyssa R.'s Photo

Pittsfield, MA

from
$15/hr
5 years experience
Pet transportation
pet walking
pet sitting
Hello! I'm Alyssa an experienced and compassionate pet sitter dedicated to providing your pets with the love and care they deserve when you're away. Whether it's daily walks, overnight stays, or playtime, I offer personalized care tailored to your pet's needs. From dogs and cats to smaller pets, I treat every furry (or scaly!)...
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Jannai B.'s Photo

Pittsfield, MA

from
$15/hr
4 years experience
Pet walking
pet sitting
Hi! I'm Jannai, and I'm a caring and dependable dog sitter who truly loves working with animals. I treat every dog like family--whether it's playtime, walks, feeding, or just keeping them company so they feel safe and loved while you're away. I'm patient, gentle, and attentive to each dog's personality and routine. I make sure...
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Grace G.'s Photo

Part-time Caregiver Available

Pittsfield, MA

from
$15/hr
4 years experience
Pet transportation
pet walking
pet sitting
daily feeding
I provide dog sitting, dog walking, at your own home. I have attended camps and trainings and love dogs of all breeds and sizes.
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Wendi H.'s Photo

Pet Care Provider

Pittsfield, MA

from
$20/hr
10 years experience
Pet sitting
Hello! I am currently seeking a part time pet or house sitting position. I have been sitting two wonderful cats (and their house) for the last two years in Stockbridge, Ma. Their owner has recently relocated out of state and now I'm looking for my next fur babies to watch! I am comfortable with cats or dogs, small or large, and...
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Karlee C.'s Photo

Pittsfield, MA

from
$15/hr
2 years experience
Pet walking
pet sitting
As a lifelong animal lover--especially cats, I'm excited to offer my pet-sitting services through Care. com. I have experience caring for dogs, cats, and small animals, providing everything from feeding and walking to playtime and cuddles. Your pet's safety and happiness are my top priorities, and I'll treat them like my own...
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Crystal M.'s Photo

Pittsfield, MA

from
$12/hr
10 years experience
I have been dog sitting for over 10 years. I love all animals . I am reliable and have my own vehicle for transporting. I am a non smoker.
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Dominic C.'s Photo

Adams, MA

from
$20/hr
10 years experience
Pet walking
pet sitting
Hello. I am Dominic (Pronounced Dominique), and I have been residing in the Berkshires since 2019. Previously I was born and raised in Miami, FL. I have over a decade worth of pet sitting with animals of all kinds. Dogs, cats, fish, birds (verbal and non verbal), lizards and amphibians. I look forward to meeting you and your...
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Pet walking
pet sitting
I've been pet and farm sitting for over 10 years, looking after everything from cats and dogs to horses, alpacas, goats, and chickens. Every animal is different, and I enjoy getting to know their personalities and making sure they feel safe and loved while their people are away. I stick closely to your routines, feeding...
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Kristen U.'s Photo

Dog Walker, Sitter

Petersburg, NY

from
$16/hr
Pet walking
pet sitting
daily feeding
I absolutely love all animals!!!! If I could spend everyday all day with them I would!!! I have 3 dogs of my own.. they are my world!! Iam trust worthy, reliable, and honest!!
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Krista S.'s Photo

Averill Park, NY

from
$16/hr
8 years experience
Hello, my name is Krista. I love animals and have been a pet sitter for years. I am always happy to help out and am very flexible. I will do my best to learn the routines and requirements for each job and apply them so I don't disrupt what they are used to. I have worked with animals of all ages and with all kinds of needs. This...
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Melanie W.'s Photo

Overnight/vacation Pet Sitting And House Sitting

Lee, MA

from
$20/hr
6 years experience
Dog training
pet walking
pet sitting
administration of medicine
I have worked with many family pets over the years, mainly dogs but also enjoy cats! I love how they have such good hearted energy (for the most part). I myself used to have a dog with behavioral challenges and have a lot of experience with that. I have done dog walking and stayed with dogs overnight over the past 6 or so...
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Korey T.'s Photo

Charlemont, MA

from
$15/hr
5 years experience
Pet walking
pet sitting
I've always been a huge animal lover & enjoy meeting every animal I encounter! For over 5 years I have worked as a dog walker/pet sitter for the same client, doing daily weekday visits for walks /feeds, as well as extended sitting/administering meds/ clean up for a dog & senior cat. My availability has opened up so I'm hoping...
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Amanda D.'s Photo

Lenox Dale, MA

from
$21/hr
6 years experience
Grooming
dog training
pet walking
pet sitting
boarding
+ 1 more
Hi! I'm Amanda, and I'm a huge dog lover. I spent three years working as a receptionist at a vet clinic, where I gained a lot of valuable knowledge. For over seven years, I've been dog sitting, providing plenty of love, walks, and affection--I treat every dog like they're my own! I can offer boarding, but I prefer to care for...
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Brooke J.'s Photo

Part-time Pet Sitting

North Adams, MA

from
$15/hr
5 years experience
Pet transportation
pet walking
pet sitting
HI! I provide dog/pet sitting in your own home, as I am a college student living on campus. I've been pet sitting for about 6 years, between friends, family, and babysitting, I've had tons of experience with all breads, sizes, and ages! I have great references and I love all dogs!
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Showing 1 - 19 of 19

  • 19 dog sitters are listed on Care.com

  • The average post rate is $25.00/hr as of March 2026

Common dog sitting questions in Cheshire, MA

Finding a trusted dog sitter in Cheshire, MA starts with understanding your dog’s needs, whether that includes daily visits, overnight care, or extended stays while you’re away. Many pet owners compare sitter profiles based on experience, availability, reviews, and services offered before making a decision. Some families also explore related services like doggy day care or hiring local dog walkers depending on their schedule and care needs.

Dog sitters in Cheshire, MA provide a range of services to keep pets safe, comfortable, and cared for while their owners are away. Common services include feeding, walking, playtime, administering medication, and overnight stays. Some sitters also provide grooming support or coordinate care with services like dog groomers to keep pets clean and healthy during longer stays.

The average rate for dog sitters in Cheshire, MA on Care.com as of March, 2026 is $25.00 per hour. Rates can vary depending on the type of care needed, such as drop-in visits, overnight stays, or extended care, as well as the sitter’s experience and number of pets. Many families compare rates alongside other pet care options in Cheshire when deciding what works best for their dog.

Choosing between a dog sitter and a kennel in Cheshire, MA depends on your dog’s personality, routine, and comfort level. Dog sitters allow pets to stay in a familiar home environment with one-on-one attention, while kennels may offer more structured social settings with other dogs. Many pet owners compare kennels vs pet sitters to determine which option best fits their dog’s needs.

Yes, many dog sitters in Cheshire, MA offer overnight care, which can be helpful for dogs that need consistent attention, companionship, or supervision during the night. Overnight dog sitting is a popular option for travel, work trips, or extended time away from home, allowing pets to maintain their routine in a comfortable environment.

Introducing your dog to a new sitter in Cheshire, MA should be done gradually to help build trust and reduce anxiety. Many pet owners schedule a meet-and-greet so the dog can become familiar with the sitter before the first booking. Following tips for introducing dogs to new people can help create a smooth transition and a positive experience for both the sitter and your pet.

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Additional Dog Sitter Services

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  • Dog Sitters in Adams, MA
  • Dog Sitters in Pittsfield, MA
  • Dog Sitters in North Adams, MA
  • Dog Sitters in Charlemont, MA
  • Dog Sitters in Petersburg, NY
  • Dog Sitters in Lenox Dale, MA
  • Dog Sitters in Lee, MA
  • Dog Sitters in Averill Park, NY
  • Dog Sitters in Whitingham, VT
  • Dog Sitters in Shelburne Falls, MA
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