House Sitting in Chester

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Top rated Chester house sitters

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Sitter Profile Image: McKenna P.
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McKenna P.
Star Sitter
from
$75
per night
5 out of 5.0 stars
343 reviews
135 repeat clients
8 years of experience
Lenox, MA, 01240

McKenna was able to help with our Aussie-doodle at short notice and we are so grateful! They had a fun day together and she helped him to be active and busy instead of in his kennel for a very long day. McKenna has a lot of experience and knowledge about what dogs need. She communicates regularly and sent some photos during the day as well. Thank you McKenna!!

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Teri T.
Sitter Profile Image: Ash T.
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Ash T.
Star Sitter
from
$40
per night
5 out of 5.0 stars
46 reviews
22 repeat clients
12 years of experience
Florence, MA, 01062

Ash was a GREAT house and pup took care of Whitney for 10 days while we were away with tons of walks, meals and treats, cuddles and rubs and overnight stays, long walks and visits with her best dog friend, and even handled a contractor visit and an appliance installation! Both our home and our pup were in great shape when we got back- would recommend Ash for six stars if i could.

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Gordon A.
Sitter Profile Image: Lori L.
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Lori L.
Star Sitter
from
$120
per night
5 out of 5.0 stars
83 reviews
33 repeat clients
15 years of experience
Greenfield, MA, 01301

We had a great experience with Lori house sitting our American Bully & Pit mix. Lori asked questions ahead of time, reviewed our instructions, and sent us text and photo updates. We couldn't have asked for anything more. We really appreciated all of her communication.

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Courtney B.
Sitter Profile Image: Elizabeth B.
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Elizabeth B.
from
$36
per night
5 out of 5.0 stars
5 reviews
1 repeat client
1 year of experience
Lee, MA, 01238

Elizabeth took great care of our dog while we went away!! She sent us pictures and gave us updates making our vacation enjoyable knowing we left our 4 legged kid in great hands! Definitely would recommend her care for your family pets 🐶🐶

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Joel G.
Sitter Profile Image: Taylor W.
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Taylor W.
from
$68
per night
5 out of 5.0 stars
4 reviews
20 years of experience
Lee, MA, 01238

Taylor was responsive and attentive. Will use her again.

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Kim P.
Sitter Profile Image: Ace G.
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Ace G.
from
$60
per night
5 out of 5.0 stars
63 reviews
21 repeat clients
9 years of experience
Chicopee, MA, 01020

Ace is ABSOLUTELY THE BEST!!! Ace is so caring, compassionate, and dedicated to the happiness of her Adopted Fur Babies.... Which funnels through to the Fur Babies Momma. Ace is in constant communication and asks questions to assist with the Fur Babies happiness. We looked forward to all the pictures that Ace sent us. We could tell from these pictures that our Fur Babies were well taken care of and happy. Ace follows the plan of care so well, of course, Clyde and Bella are there to assist. lol Ace was so respectful of our home and left it in the same neatness as upon arrival. If I could, I would give ACE 10 stars!!!!! 🐾🐾💕

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Michele A.
Sitter Profile Image: Erin O.
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Erin O.
Star Sitter
from
$70
per night
5 out of 5.0 stars
24 reviews
8 repeat clients
20 years of experience
Westfield, MA, 01085

Erin did a great job taking care of our dog and house. Our dog was healthy and happy when we returned home and our house was exactly as we had left it. We hope Erin is available the next time we travel.

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Cynthia S.
Sitter Profile Image: Matt L.
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Matt L.
Star Sitter
from
$70
per night
5 out of 4.9 stars
64 reviews
17 repeat clients
32 years of experience
Hadley, MA, 01035

Matt and Ziggy had a great time together while I was out of town for the weekend. Matt was also a great housesitter; he left my place spotless.

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Greg P.
Sitter Profile Image: Skylar R.
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Skylar R.
from
$50
per night
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: Isabella M.
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Isabella M.
from
$32
per night
5 out of 5.0 stars
2 reviews
1 repeat client
18 years of experience
Easthampton, MA, 01027

Best experience! Super communicative sending pics /videos so I felt secure in my pups comfort after dedicated efforts that softened my ornery, timid chihuahua into a cuddle buddy eager for love and attention.

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Jess N.
Sitter Profile Image: Kelly H.
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Kelly H.
from
$125
per night
5 out of 5.0 stars
65 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

Kelly was organized and attentive to every detail about our three dogs with wide ranging needs. She visited in advance, took copious notes and followed up on everything to double check. We will use her again and are very appreciative of her services.

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Marianne D.
Sitter Profile Image: Saige G.
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Saige G.
from
$40
per night
5 out of 5.0 stars
16 reviews
6 repeat clients
11 years of experience
Easthampton, MA, 01027

Saige was super polite, pleasant, and caring for all of my dogs needs. She brought my boy to the dog park, for walks, and kept him entertained. She was a perfect houseguest, and I will absolutely be booking with her again.

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Nicole B.
Sitter Profile Image: Rick W.
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Rick W.
from
$32
per night
5 out of 5.0 stars
4 reviews
1 repeat client
15 years of experience
Easthampton, MA, 01027

Rick was very personable and great with our animals! He was thorough throughout the whole pet sitting experience and we would definitely book with him again!

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jim b.
Sitter Profile Image: Shawna B.
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Shawna B.
from
$68
per night
5 out of 5.0 stars
8 reviews
3 repeat clients
15 years of experience
Westhampton, MA, 01027

Shawna provided wonderful care for our two small dogs who require overnight company. We are very satisfied with Shawna's level of care and would like to rebook her services in the future!

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Ray O.
Sitter Profile Image: Rachel B.
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Rachel B.
from
$40
per night
5 out of 5.0 stars
2 reviews
1 repeat client
18 years of experience
westfield, MA, 01085

Rachel was great. She was very patient with our elderly dog. Excellent communication!

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Marjorie P.
Sitter Profile Image: Grace E.
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Grace E.
from
$75
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
10 years of experience
South Lee, MA, 01260

Grace took care of our two dogs overnight. She kept us informed and sent pictures. When we returned the house was clean and the dogs were happy. We would book her again in the future!

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Kim Z.
Sitter Profile Image: Jay W.
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Jay W.
from
$30
per night
5 out of 5.0 stars
3 reviews
1 repeat client
32 years of experience
Russell, MA, 01071

About: Hello fur parents! My name is Jay and I’m so grateful you’re letting me hang out with your baby for a bit! I like dogs for more than I like people and have trained my own dogs- house breaking, therapy dog training, tricks, even retraining one dog to like men again after a scare during one of her puppy fear periods. I can’t wait to meet your baby! I’m accustomed to all sizes and breeds- I have raised and trained black labs, Siberian huskies, golden retrievers, boarder doodles, and mix breeds (my own and then I help my extended family train their dogs as well). The more fur, the more yap, the more jumping up and down, the more kisses, the better in my opinion! I am quite flexible at this time and am willing to work with you and your babies to make sure they are well loved and taken care of! However you wish for your baby to be taken care of, that is what I will do! I have a 6 year old Shiz-Tzu mix that I would be thrilled to bring along if your baby would like company.

Sitter Profile Image: John H.
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John H.
from
$32
per night
22 years of experience
Chesterfield, MA, 01012

About: I have over twenty years of experience in pet care. I have worked at boarding facilities, in pet grooming boutiques, in retail pet stores, and have done a fair share of dog walking and pet sitting. I am freelance illustrator and graphic designer, so my schedule is very flexible at the moment. I also have weekends free to do house sitting I believe I would bring compassion as well as experience to the job. I am extremely responsible and reliable 40 year-old animal lover willing to get my hands dirty and work hard.

Sitter Profile Image: Madeline T.
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Madeline T.
from
$30
per night
10 years of experience
Otis, MA, 01029

About: I have watched over family members dogs before and have had to give dogs IV drips and injections so I understand the importance of having someone who will properly tend to your pets needs with compassion. I am a full time student at Loyola University and so I have a pretty flexible schedule to tend to cater to someone’s scheduling needs. I am currently living in the Universities dorms so I cannot have pets, but I have always lived in a home with one or more pets and love to share a space with them.

Sitter Profile Image: Olena I.
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Olena I.
from
$90
per night
5 out of 5.0 stars
48 reviews
18 repeat clients
15 years of experience
Middlefield, MA, 01235

Olena house and pet sat for us for 6 days and we could not ask for a more reliable and delightful person. Easy to communicate with and extremely responsible. Thank you Olena!

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Ash M.
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Sitter Profile Image: McKenna P.
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Sitter Profile Image: McKenna P.
Verified Background Check

McKenna P.
Rover 101
Star Sitter

Avid Dog Lover and Sitter
Lenox, MA, 01240
16.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 5.0 stars
343 reviews
135 repeat clients
Profile image

McKenna was able to help with our Aussie-doodle at short notice and we are so grateful! They had a fun day together and she helped him to be active and busy instead of in his kennel for a very long day. McKenna has a lot of experience and knowledge about what dogs need. She communicates regularly and sent some photos during the day as well. Thank you McKenna!!

Availability updated 5 days ago
Sitter Profile Image: Ash T.
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Sitter Profile Image: Ash T.
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Ash T.
Star Sitter

Experienced Dog Caregiver
Florence, MA, 01062
14.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
46 reviews
22 repeat clients
Profile image

Ash was a GREAT house and pup took care of Whitney for 10 days while we were away with tons of walks, meals and treats, cuddles and rubs and overnight stays, long walks and visits with her best dog friend, and even handled a contractor visit and an appliance installation! Both our home and our pup were in great shape when we got back- would recommend Ash for six stars if i could.

Availability updated 6 days ago
Sitter Profile Image: Lori L.
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Sitter Profile Image: Lori L.
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Lori L.
Star Sitter

Reliable & Caring for your Family
Greenfield, MA, 01301
28.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$120
per night
5 out of 5.0 stars
83 reviews
33 repeat clients
Profile image

We had a great experience with Lori house sitting our American Bully & Pit mix. Lori asked questions ahead of time, reviewed our instructions, and sent us text and photo updates. We couldn't have asked for anything more. We really appreciated all of her communication.

Availability updated 11 days ago
Sitter Profile Image: Elizabeth B.
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Sitter Profile Image: Elizabeth B.
Verified Enhanced Background Check

Elizabeth B.

Loving your pets while you’re away!
Lee, MA, 01238
14.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$36
per night
5 out of 5.0 stars
5 reviews
1 repeat client
Profile image

Elizabeth took great care of our dog while we went away!! She sent us pictures and gave us updates making our vacation enjoyable knowing we left our 4 legged kid in great hands! Definitely would recommend her care for your family pets 🐶🐶

Availability updated today
Sitter Profile Image: Taylor W.
Verified Enhanced Background Check
Sitter Profile Image: Taylor W.
Verified Enhanced Background Check

Taylor W.

Life-long dog and cat lover
Lee, MA, 01238
11.5 mi. away
House Sitting, Drop-In Visits
from
$68
per night
5 out of 5.0 stars
4 reviews
Profile image

Taylor was responsive and attentive. Will use her again.

Availability updated 4 days ago
Sitter Profile Image: Ace G.
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Sitter Profile Image: Ace G.
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Ace G.

I love animals they are healers
Chicopee, MA, 01020
20.9 mi. away
House Sitting, Drop-In Visits
from
$60
per night
5 out of 5.0 stars
63 reviews
21 repeat clients
Profile image

Ace is ABSOLUTELY THE BEST!!! Ace is so caring, compassionate, and dedicated to the happiness of her Adopted Fur Babies.... Which funnels through to the Fur Babies Momma. Ace is in constant communication and asks questions to assist with the Fur Babies happiness. We looked forward to all the pictures that Ace sent us. We could tell from these pictures that our Fur Babies were well taken care of and happy. Ace follows the plan of care so well, of course, Clyde and Bella are there to assist. lol Ace was so respectful of our home and left it in the same neatness as upon arrival. If I could, I would give ACE 10 stars!!!!! 🐾🐾💕

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Erin O.
Verified Enhanced Background Check
Sitter Profile Image: Erin O.
Verified Enhanced Background Check

Erin O.
Star Sitter

Reliable + Remote Sitter and Walker
Westfield, MA, 01085
17.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 5.0 stars
24 reviews
8 repeat clients
Profile image

Erin did a great job taking care of our dog and house. Our dog was healthy and happy when we returned home and our house was exactly as we had left it. We hope Erin is available the next time we travel.

Availability updated 9 days ago
Sitter Profile Image: Matt L.
Verified Enhanced Background Check
Sitter Profile Image: Matt L.
Verified Enhanced Background Check

Matt L.
Star Sitter

Loving Pet Sitter, Works from Home.
Hadley, MA, 01035
19.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 4.9 stars
64 reviews
17 repeat clients
Profile image

Matt and Ziggy had a great time together while I was out of town for the weekend. Matt was also a great housesitter; he left my place spotless.

Availability updated 5 days ago
Sitter Profile Image: Skylar R.
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Sitter Profile Image: Skylar R.
Verified Enhanced Background Check

Skylar R.

All around animal lover right here!
Dalton, MA, 01226
15.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
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 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Isabella M.
Verified Enhanced Background Check
Sitter Profile Image: Isabella M.
Verified Enhanced Background Check

Isabella M.

I really enjoy working with animals
Easthampton, MA, 01027
18.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$32
per night
5 out of 5.0 stars
2 reviews
1 repeat client
Profile image

Best experience! Super communicative sending pics /videos so I felt secure in my pups comfort after dedicated efforts that softened my ornery, timid chihuahua into a cuddle buddy eager for love and attention.

Availability updated 8 days ago
Sitter Profile Image: Kelly H.
Verified Background Check
Sitter Profile Image: Kelly H.
Verified Background Check

Kelly H.

At home with a kind-caring sitter
Otis, MA, 01253
8.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$125
per night
5 out of 5.0 stars
65 reviews
31 repeat clients
Profile image

Kelly was organized and attentive to every detail about our three dogs with wide ranging needs. She visited in advance, took copious notes and followed up on everything to double check. We will use her again and are very appreciative of her services.

Availability updated 5 days ago
Sitter Profile Image: Saige G.
Verified Background Check
Sitter Profile Image: Saige G.
Verified Background Check

Saige G.

Lover Of All Living Things
Easthampton, MA, 01027
15.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5 out of 5.0 stars
16 reviews
6 repeat clients
Profile image

Saige was super polite, pleasant, and caring for all of my dogs needs. She brought my boy to the dog park, for walks, and kept him entertained. She was a perfect houseguest, and I will absolutely be booking with her again.

Availability updated 3 days ago
Sitter Profile Image: Rick W.
Verified Enhanced Background Check
Sitter Profile Image: Rick W.
Verified Enhanced Background Check

Rick W.

I love all animals small and large!
Easthampton, MA, 01027
16.7 mi. away
House Sitting, Drop-In Visits
from
$32
per night
5 out of 5.0 stars
4 reviews
1 repeat client
Profile image

Rick was very personable and great with our animals! He was thorough throughout the whole pet sitting experience and we would definitely book with him again!

Availability updated 5 days ago
Sitter Profile Image: Shawna B.
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Sitter Profile Image: Shawna B.
Verified Enhanced Background Check

Shawna B.

Responsible Reliable Pet Care
Westhampton, MA, 01027
10.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$68
per night
5 out of 5.0 stars
8 reviews
3 repeat clients
Profile image

Shawna provided wonderful care for our two small dogs who require overnight company. We are very satisfied with Shawna's level of care and would like to rebook her services in the future!

Availability updated today
Sitter Profile Image: Rachel B.
Verified Enhanced Background Check
Sitter Profile Image: Rachel B.
Verified Enhanced Background Check

Rachel B.

your dog's best friend
westfield, MA, 01085
16.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
2 reviews
1 repeat client
Profile image

Rachel was great. She was very patient with our elderly dog. Excellent communication!

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

Grace E.

I make every pet my BFF!
South Lee, MA, 01260
15.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

Grace took care of our two dogs overnight. She kept us informed and sent pictures. When we returned the house was clean and the dogs were happy. We would book her again in the future!

Availability updated 10 days ago
Sitter Profile Image: Jay W.
Verified Enhanced Background Check
Sitter Profile Image: Jay W.
Verified Enhanced Background Check

Jay W.

Hi fur parents!
Russell, MA, 01071
9.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
3 reviews
1 repeat client

I've known Jay for a very long time and they have always been the biggest animal person. When we finally got a dog, he has been apprehensive of most people because of his background before we got him but Jay is one of the few people he can recognize quickly and approves of. Every dog I've ever known them to have owned or be around has been in the most caring and loving hands. Hands down would recommend them for any level of pet care!!

Availability updated 11 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: John H.
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Sitter Profile Image: John H.
Verified Enhanced Background Check

John H.

A best friend, for your best friend
Chesterfield, MA, 01012
10.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$32
per night
2 reviews

When are family is traveling away from home. It always makes me feel better, knowing that John is at are home. Watching are cats and dog, and also keeping an eye on the property. John makes sure the pets are always safe, and taken care of.

Availability updated 34 days ago
Sitter Profile Image: Madeline T.
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Sitter Profile Image: Madeline T.
Verified Enhanced Background Check

Madeline T.

Love all pets and their quirks!
Otis, MA, 01029
8.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
1 review

Maddie is a true dog lover. She is so great with our 2 dogs and any dogs she meets. She loves taking them for walks and is very careful with them. She is also great with my sisters cats. She would be a great pet sitter or walker.

Availability updated 81 days ago
Sitter Profile Image: Olena I.
Verified Enhanced Background Check
Sitter Profile Image: Olena I.
Verified Enhanced Background Check

Olena I.

24/7 Care & Cuddles
Middlefield, MA, 01235
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$90
per night
5 out of 5.0 stars
48 reviews
18 repeat clients
Profile image

Olena house and pet sat for us for 6 days and we could not ask for a more reliable and delightful person. Easy to communicate with and extremely responsible. Thank you Olena!

Availability updated 7 days ago
Confirmed availability for Labor Day Weekend

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