Pet Sitting in Pittsfield

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Adrienne H.
Sitter Profile Image: Adrienne H.
Love dogs!
Pittsfield, MA, 01021
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Adrienne always goes above and beyond when caring for our full house of animals! We have a pit mix, spaniel, 2 kitties, and fish. I trust Adrienne whole-hearted… (more)

from

$20

per visit
Calendar Recently Updated
Sitter Profile Image: Sandy M.
Sitter Profile Image: Sandy M.
2.
Furry and Family Go Together
Pittsfield, MA, 01201
Boarding, Drop-In Visits

I had recently moved to The Berkshires from Boston and needed a new cat sitter so I could go on vacation. This was my first time using Rover, so I wasn't sure w… (more)

from

$20

per visit
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Jess L.
Sitter Profile Image: Jess L.
3.
I care for the care of your pets
Pittsfield, MA, 01201
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jess is great with our dogs. She has watched the two of our dogs on multiple occasions and sometimes 3 or 4. She takes the time out of her day to make sure they… (more)

from

$19

per visit
Sitter Profile Image: Jahna S.
Sitter Profile Image: Jahna S.
4.
Promise to love your dog as my own!
Pittsfield, MA, 01201
Drop-In Visits, Dog Walking

Jahna’s very friendly and my dog loves her! She showed up on time and sent me picture updates; my pup sure looks happy! I look forward to using her services aga… (more)

from

$16

per visit
Calendar Recently Updated
Sitter Profile Image: David K.
Sitter Profile Image: David K.
5.
Stay at home dog dad
Pittsfield, MA, 01201
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

David is hands-down the best pet parent I know and their dogs live a life I could only dream of. With carefully cultivated meals, enrichment toys and treats, lo… (more)

from

$15

per visit
Calendar Recently Updated
Sitter Profile Image: Rick & Autumn C.
Sitter Profile Image: Rick & Autumn C.
Loving Doggy Care
Pittsfield, MA, 01201
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sometimes when I have to work really long days I let Rick look after my dog. I always tell him he should try to make this a buisness so I think a platform like … (more)

from

$19

per visit
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Brianna W.
Sitter Profile Image: Brianna W.
Trustworthy and always punctual.
Pittsfield, MA, 01201
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Completely wonderful! On time, friendly, great with my 2 huge dogs, super nice. She will definitely be the person I contact when I need help with the dogs in th… (more)

from

$18

per visit
Calendar Recently Updated
Sitter Profile Image: Becca S.
Sitter Profile Image: Becca S.
8.
Lover of all animals big and small!
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Dog Walking

I can't say enough about Becca. She's responsible, loving and very caring. She will treat your pet like her owne. I've watched her with her owe dog and he love… (more)

from

$15

per visit
Sitter Profile Image: Logan A.
Sitter Profile Image: Logan A.
9.
Dog Groomer & Pet Sitter.
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Dog Walking

About: I've had and lived with cats and dogs. I have regularly cat and dog sat for friends and family in the past successfully and find it rewarding. I am … (more)

from

$20

per visit
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Shayla H.
Sitter Profile Image: Shayla H.
10.
PAWSOME opportunities for your dog!
Lenox, MA, 01240
Drop-In Visits, Dog Walking

Shayla is amazing! She came and picked Nala up and brought her on an amazing 3 mile hike. She made sure I was comfortable by sending me pictures and letting me … (more)

from

$15

per visit
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Mary H.
Sitter Profile Image: Mary H.
11.
Lots of snuggles and love!
Pittsfield, MA, 01201
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Mary is a fantastic cat sitter and was always on time! Her updates with photos kept my mind at ease while I was on vacation. Mary was responsible and answered e… (more)

from

$25

per visit
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Trinity L.
Sitter Profile Image: Trinity L.
12.
Flexible schedule. Cats and dogs!
Dalton, MA, 01226
House Sitting, Drop-In Visits, Dog Walking
8 years of experience

About: I’ve taken care of dogs my whole life. I am an experienced sitter who you can trust to take amazing care of your pup. I take any (and all) opportunit… (more)

from

$21

per visit
Sitter Profile Image: Kai C.
Sitter Profile Image: Kai C.
13.
Kai 
Verified Enhanced Background Check
Rover 101
I'll run with + love your dog
Pittsfield, MA, 01201
Boarding, House Sitting, Drop-In Visits, Dog Walking

My dog loves Ashley! I'm so glad that shes available to let my dog have a bathroom break, some lunch and belly scritches or play time. I highly recommend Ashley… (more)

from

$22

per visit
Sitter Profile Image: Jenna G.
Sitter Profile Image: Jenna G.
14.
vacations for animals big and small
pittsfield, MA, 01201
Drop-In Visits, Dog Walking

Jenna volunteers with a rescue I run Mountain Rottie Rescue. She has fostered many dogs for us. She does not always know the temperament of the dogs she will … (more)

from

$22

per visit
Sitter Profile Image: Maggie H.
Sitter Profile Image: Maggie H.
15.
I LOVE dogs
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Dog Walking
2 years of experience

About: Animals are a big part of my life! I used to volunteer frequently at animal shelters helping walk and train dogs. Cats can be sassy but also sweet! A… (more)

from

$15

per visit
Sitter Profile Image: Alaina S.
Sitter Profile Image: Alaina S.
16.
Must love dogs
Pittsfield, MA, 01201
Drop-In Visits, Dog Walking
15 years of experience

About: I’ve had and taken care of pets since I was a young child. I have 20 years experience dog sitting for one or multiple dogs. I am currently out of wo… (more)

from

$20

per visit
Calendar Recently Updated
Sitter Profile Image: Nelly B.
Sitter Profile Image: Nelly B.
17.
My dogs are my annoying siblings
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Dog Walking

Nelly was great with our dogs. We received photos every time she did a drop in, she went above and beyond definitely recommend. (more)

from

$35

per visit
Sitter Profile Image: Ambar G.
Sitter Profile Image: Ambar G.
18.
Energetic and Fun Caring Sitter
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Dog Walking

I've known Ambar for a while now, and her dedication to making sure the pets under her care are happy is admirable. She puts in a lot of effort to maintain the … (more)

from

$18

per visit
Sitter Profile Image: Jenna H.
Sitter Profile Image: Jenna H.
19.
Loving pet sitter
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Dog Walking

She is very good with animals, she knows how to handle them when they misbehave and she knows when to reward good behavior. She is very dependable and responsib… (more)

from

$15

per visit
Sitter Profile Image: Ava-Lena S.
Sitter Profile Image: Ava-Lena S.
Loving, reliable and attentive!
Pittsfield, MA, 01201
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Highly recommend! Ava-Lena was so accommodating to our schedule, very responsive and so nice. Absolutely will be using again! (more)

from

$20

per visit

Rover.com is the simple, savvy way to find and book drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have worked through Rover for years pet sitting, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter on Rover. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

Drop-In Visits