House Sitting in Winchester

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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Halley W.
1.
Animal-loving College Student!Newton, MA, 02465
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Halley is the sweetest person, especially when caring for your pups! She’s helped me with my senior dogs when they were having medical issues and she was so att… (more)

from
$65
per night
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Grace S.
2.
ISO furry friends 🐶Allston-Brighton, Brighton, MA, 02135
House Sitting, Drop-In Visits, Dog Walking

Grace is a good family friend of ours, and when she was in high school, she would dog sit for us often. She was able to accommodate for both our puppy shih tzu … (more)

from
$45
per night
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Jordan C.
3.
Aspiring vet and labrador ownerWakefield, MA, 01880
House Sitting, Drop-In Visits, Dog Walking

I hired Jordan to watch my corgi Polly during my wedding reception. The reception was taking place at a family members house. Polly was very eager to be outside… (more)

from
$70
per night
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Eva K.
4.
Eva 
Verified Enhanced Background Check
I just really love dogsSomerville, MA, 02144
House Sitting, Drop-In Visits, Dog Walking

Eva was truly fantastic - she was great with Dakota and respectful of the house. When we got home, the bedsheets and the house were clean and Dakota was content… (more)

from
$45
per night
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Steven G.
5.
Patient, Fun, training and love!Everett, MA, 02149
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Steven was the most professional dog-sitters we have ever encountered. He went above and beyond, asked great questions, took good care of our senior pups, and d… (more)

from
$55
per night
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Your pets, I and cuddles!Malden, MA, 02148
House Sitting, Drop-In Visits, Dog Walking

Tamirez has been caring for my pets for over 2 years now. Wether it’s for one night or a whole week I always know I can count on her for a worry free time knowi… (more)

from
$50
per night
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travel nurse needing her dog fix 🙃Woburn, MA, 01801
House Sitting, Drop-In Visits, Dog Walking

This was my first time having someone watch my dogs in my home and Priscilla was an absolute angel and joy! She has a calm and positive energy, was very caring … (more)

from
$75
per night
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Animal lover and avid walker!Somerville, MA, 02143
House Sitting, Drop-In Visits, Dog Walking

I can't say enough good things about Kathryn, who took care of our mini Golden doodle for a week in our home. Our dog, who is typically anxious and takes a whil… (more)

from
$65
per night
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Can’t wait to meet your pet!!Somerville, MA, 02144
House Sitting, Drop-In Visits, Dog Walking

Julia was an amazing pet sitter, Moby loved her right away. I love that Julia was very responsible she arrived on time, was attentive to Moby's care routine and… (more)

from
$60
per night
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10.
Animal loving educator!Somerville, MA, 02144
House Sitting, Drop-In Visits, Dog Walking

Conner kept us informed about our cats and sent pictures. The communication was good and we knew that our cats were safe and well taken care of. (more)

from
$40
per night
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Keep the vet away by a walk a day!Medford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

I have known Elizabeth for almost 4 years now. She connected with our two dogs instantly! Elizabeth has such a loving nature so Ellie and Koda fell in love with… (more)

from
$65
per night
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12.
The Crate Escape: Cats & DogsMedford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

We had Ruby stay at our house in Southie and watch our two dogs for a long weekend. She was incredibly professional and responsive. We would absolutely recommen… (more)

from
$45
per night
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13.
Liz 
Verified Background Check
Lifelong animal lover!Winchester, MA, 01890
House Sitting, Drop-In Visits, Dog Walking

Liz was great! She took great care of Dasher and the apartment as well. Everything was spotless when I returned and I had a very happy dog!! Will definitely be … (more)

from
$70
per night
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14.
Never met a dog I didn’t love!SOMERVILLE, MA, 02143
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Highly recommend! Tara watched our two dogs for one night and we could not have asked for a better experience. She was communicative, on time, and trustworthy. … (more)

from
$60
per night
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15.
Giving pets love and care.Arlington, MA, 02474
House Sitting, Drop-In Visits, Dog Walking

Bob has been an absolutely incredible dog sitter for my dog, Charlotte. I often joke that he’s more of an uncle to her than a dog sitter! He cares and loves for… (more)

from
$150
per night
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16.
A girl who will love your fur baby!Stoneham, MA, 02180
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Julia has always loved dogs for her whole life. Everywhere she goes, if she ever runs into a dog she immediately gives the dog as much love and affection as she… (more)

from
$55
per night
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17.
Our pets deserve the bestMalden, MA, 02145
House Sitting

Lyndsay watched our pup for a weekend and did an awesome job! His communication was great and he took great care of our pup while being mindful of the notes we … (more)

from
$50
per night
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18.
Fitness goals! Pet More dogs!Malden, MA, 02148
House Sitting, Drop-In Visits, Dog Walking

Erin did a fantastic job watching our dog. She sent us constant photos and Olive was well taken care of. We’d have Erin watch her anytime!!! (more)

from
$32
per night
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Fully Remote Workers Who Love PETS!Woburn, MA, 01801
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Wow! Could not have been happier! Jason and Dina were excellent sitters that far exceeded my expectations. I got regular updates and my very active Golden R… (more)

from
$150
per night
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20.
Drop in visits by a pet lover!Medford, MA, 02155
House Sitting, Drop-In Visits

Jessica was great! My dog liked her immediately, she came when she said she would, and sent great updates. I'll definitely use her again next time I'm out of to… (more)

from
$38
per night

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