House Sitting in Winchester

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Calendar Recently Updated
Sitter Profile Image: Angelic S.
Sitter Profile Image: Angelic S.
Puppy Love
Arlington, MA, 02474
Boarding, House Sitting, Drop-In Visits, Dog Walking

Angy did a wonderful job sitting at our house with Igloo for about a week. She took him on nice long walks, kept him company and gave us updates. She also kep… (more)

from

$120

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Frances & Julia H.
Sitter Profile Image: Frances & Julia H.
Kind, caring & trustworthy tag team
Reading, MA, 01867
House Sitting, Drop-In Visits, Dog Walking

Fran has cared for our animals many times, and always treats them as her own. She is both a dog person, and a cat person. I always know our pets will be in good… (more)

from

$80

per night
Sitter Profile Image: Salina B.
Sitter Profile Image: Salina B.
3.
I'll love your pet like my own
Medford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

Salina did a great job with my dog. My dog was particularly anxious this weekend because we have very recently moved but Salina handled it well and kept me upda… (more)

from

$50

per night
Calendar Recently Updated
Sitter Profile Image: Jasmina C.
Sitter Profile Image: Jasmina C.
Ready to take care of your pet!
Arlington, MA, 02474
House Sitting, Drop-In Visits, Dog Walking

Jasmina is a fabulous caretaker and a real animal lover! She watched our two dogs and cats and seemed totally in her element navigating their dynamics and follo… (more)

from

$32

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: McKinley M.
Sitter Profile Image: McKinley M.
Experienced, Loving Pet Sitter
Woburn, MA, 01801
House Sitting, Drop-In Visits, Dog Walking

McKinley is incredible with all 3 of my fur babies. I feel at complete peace going away knowing that they’re in her care. She is extremely reliable and responsi… (more)

from

$50

per night
Calendar Recently Updated
Sitter Profile Image: Andrew T.
Sitter Profile Image: Andrew T.
6.
Friendly, convenient sitter/walker
Medford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

We are so lucky to have Andrew as a sitter. He is very professional and easy to communicate with. He is also great with our puppy who has a lot of energy. We we… (more)

from

$75

per night
Sitter Profile Image: Zel M.
Sitter Profile Image: Zel M.
7.
Zel 
Verified Enhanced Background Check
Pro Pet Sitter
Arlington, MA, 02476
House Sitting

Zel was fantastic with our older great Pyr mix who has become used to being with us all the time through pandemic days. She soothed our dog's anxiety and took … (more)

from

$75

per night
Calendar Recently Updated
Sitter Profile Image: Courtney J.
Sitter Profile Image: Courtney J.
Energetic animal lover
Malden, MA, 02148
House Sitting, Drop-In Visits, Dog Walking

Courtney was fantastic, she is very responsive, timely and just overall wonderful. One of our dogs is nervous and very needy and he has a great time! (more)

from

$75

per night
Calendar Recently Updated
Sitter Profile Image: Lexi K.
Sitter Profile Image: Lexi K.
9.
Be at ease while you’re away!
Wilmington, MA, 01887
House Sitting

Lexi took an amazing care of my daughter of 4 paws while we were traveling. She sent me a lot of videos and photos, I was at ease while traveling, came back to … (more)

from

$97

per night
Calendar Recently Updated
Sitter Profile Image: Katherine C.
Sitter Profile Image: Katherine C.
Active & will take care of your pup
Malden, MA, 02148
House Sitting, Drop-In Visits, Dog Walking

Katherine was super communicative and extremely professional. I was running around crazy and I set her up with a not-so-ideal situation, but she handled it so w… (more)

from

$45

per night
Calendar Recently Updated
Sitter Profile Image: Ana R.
Sitter Profile Image: Ana R.
11.
Ana 
Verified Enhanced Background Check
Rover 101
Your Dog's New Best Friend
Somerville, MA, 02144
House Sitting, Drop-In Visits, Dog Walking

Ana did a fantastic job with Rue. I came home to a happy dog. That’s all you can ask for. She also left the house in wonderful shape - it was as if she’d never … (more)

from

$75

per night
Calendar Recently Updated
Sitter Profile Image: Illeanna G.
Sitter Profile Image: Illeanna G.
Crazy Dog Lady
MEDFORD, MA, 02155
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Anna did a great job with our puppy when we went out of town for a long weekend. She sent lots of photos and updates. We have already booked her for another tri… (more)

from

$85

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: James P.
Sitter Profile Image: James P.
13.
Love of all paws, claws, and flaws
Woburn, MA, 01801
House Sitting, Drop-In Visits, Dog Walking

My dogs loved James! I can definitely recommend him for everyone! I have an adult and a puppy and he took good care of them! (more)

from

$90

per night
Calendar Recently Updated
Sitter Profile Image: Megan M.
Sitter Profile Image: Megan M.
14.
Caring Vet Tech Assistant
Medford, MA, 02155
House Sitting

Megan did a great job caring for our cats while we were away. She checked in with us and sent pictures. If I had questions she was very responsive. The cats wer… (more)

from

$85

per night
Calendar Recently Updated
Sitter Profile Image: Julia G.
Sitter Profile Image: Julia G.
15.
Animal lover and nature educator!
Medford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

My dogs love Julia! I have one big dog and one little dog and she is so sweet around them and gives them so much love. Julia is also great at sensing their mood… (more)

from

$50

per night
Calendar Recently Updated
Sitter Profile Image: Monyka K.
Sitter Profile Image: Monyka K.
16.
Your dog’s partner in crime
Cambridge, MA, 02140
House Sitting, Drop-In Visits, Dog Walking

About: I have a 6 year old Chiweenie of my own. I Rescue her when she was a puppy. I am a very loving, patient flexible and energetic sitter. Had dog sit for dog fri… (more)

from

$70

per night
Calendar Recently Updated
Sitter Profile Image: Bekk C.
Sitter Profile Image: Bekk C.
17.
Professional pet care of all kinds!
Medford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

I wouldn’t trust anyone with my pets more than Bekk! They have years of experience with all kinds of animals. They’ve worked with dogs for years and have helped… (more)

from

$70

per night
Sitter Profile Image: Kathryn F.
Sitter Profile Image: Kathryn F.
18.
Full-time animal lover!
Burlington, MA, 01803
House Sitting, Drop-In Visits, Dog Walking

My cat is normally extremely unhappy when I’m away, even when it’s with my partner she used to live with. I’ve never come back to her so contented, and constant… (more)

from

$85

per night
Calendar Recently Updated
Sitter Profile Image: Tammy B.
Sitter Profile Image: Tammy B.
19.
Fun person with 5 years experience!
Medford, MA, 02155
Boarding, House Sitting, Drop-In Visits, Dog Walking

Tammy was professional, attentive to Carlow’s needs and peculiarities, and easy to deal with. She sent photos, and it eased my mind to see Carlow looking relaxe… (more)

from

$90

per night
Calendar Recently Updated
Sitter Profile Image: Lauren F.
Sitter Profile Image: Lauren F.
20.
Thoughtful and loving pet sitter 🐶
Melrose, MA, 02176
House Sitting, Drop-In Visits, Dog Walking

Lauren is a former co-worker turned friend of mine who I trust to stay in my home and care for my beloved dog when I go on long trips. She is trustworthy, punct… (more)

from

$60

per night

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House Sitting