House Sitting in Winchester

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

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Laura G.
1.
Professional, reliable dog lover!Belmont, MA, 02478
House Sitting

Laura is an amazing person and dog sitter/lover. It’s in her blood! She took care of my dogs in my apt for a few months while I was dealing with a sudden emerge… (more)

from
$125
per night
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Melissa T.
Dog-lover eager to help pet owners!Somerville, MA, 02143
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

dog didn’t miss me at all and complained when Melissa left. seems like my dog is a bit traitorous ?. she was super communicative and helpful throughout my trip,… (more)

from
$50
per night
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Hallye M.
3.
Every weather walker, rain or snow!Medford, MA, 02155
House Sitting, Drop-In Visits, Dog Walking

About: Growing up in a home with cats, dogs, and fish (plus the nearby countryside), I have always adored being around animals and taking care of them. S… (more)

from
$50
per night
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Dana T.
4.
Active young professional-flexibleSomerville, MA, 02143
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

She was great! Communicated well and did a great job with my dog! (more)

from
$60
per night
Confirmed availability: Memorial day
Ja'Dana E.
College grad-gap yearNeighborhood 9, Cambridge, MA, 02140
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Ja’dana stayed with our dog four nights and kept her company and took care of her amazingly. She followed all of our instructions and double checked when she wa… (more)

from
$75
per night
Confirmed availability: Memorial day
6.
Go on Vacation Worry-Free!Winchester, MA, 01890
House Sitting, Drop-In Visits, Dog Walking

Would like to thank Dexter for watching our Franky. It’s the first time we left him with a sitter and we were nervous, he made us feel calm and that Franky was … (more)

from
$50
per night
Confirmed availability: Memorial day
7.
Ed 
Verified Background Check
Pawesome adventures await!Arlington, MA, 02474
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ed was amazing! My cat Tiger was worried about our move and doesn’t like to be alone and Ed did so great with him. He got Tig to come out of his hiding spot and… (more)

from
$60
per night
8.
Must love dogsMelrose, MA, 02176
House Sitting, Drop-In Visits, Dog Walking

Mike was so great! Our pups loved him right away. He kept us posted each visit and we felt so great knowing Gunner was in such great hands while we were away. W… (more)

from
$45
per night
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Dog and animal lover extrodinaireWoburn, MA, 01801
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Rebecca is awesome with dogs (and all animals). She has watched my dog when we went on vacation and has walked him many times over the past several years. My do… (more)

from
$50
per night
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10.
Active, friendly neighbor!Belmont, MA, 02478
House Sitting, Drop-In Visits

Angela was great! I'm so glad she and Olive had a good time. I was completely at ease with Angela in my home and taking care of my most precious companion. Than… (more)

from
$40
per night
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11.
Nurse who loves animals and people!Burlington, MA, 01803
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Heidi did a wonderful job looking after my two dogs! She provided frequent updates while I was away and really cared about their well-being. Would confidently r… (more)

from
$35
per night
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12.
Caring Vet Tech AssistantMedford, MA, 02155
House Sitting, Drop-In Visits

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
$60
per night
Confirmed availability: Memorial day
Puppy love! Loving your best friendWoburn, MA, 01801
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Claudine helped us out with a last minute dog sitting request. She took great care of our dog and apartment over the weekend. We are so appreciative of her resp… (more)

from
$70
per night
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Vet Tech Assistant looking for workWoburn, MA, 01801
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Mackenzie is an awesome pet lover who has shown loving and caring services for many of our furry children from dogs to ducks ( cats, goats, horses ,bunnies , be… (more)

from
$28
per night
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The Best Care For Your Best FriendSomerville, MA, 02144
House Sitting, Drop-In Visits, Dog Walking

Courtney house sat for us and watched our puppy. She was very communicative and great with the pup. Would certainly recommend! (more)

from
$40
per night
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16.
Weekend dog lover!Malden, MA, 02148
Dog Boarding, House Sitting, Dog Walking

Kate was great, she communicated with me and my dogs were happy when we came home! (more)

from
$40
per night
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17.
Living the dream!Stoneham, MA, 02180
House Sitting, Drop-In Visits, Dog Walking

Natasha stayed at my house and watched my dogs while I was away for a few days. She came over for a meet & greet beforehand, and my pups took to her immediately… (more)

from
$40
per night
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18.
Care and fun hikes for your dog!Stoneham, MA, 02180
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I’m a musician,violin teacher, pet sitter and dog walker. I love and respect all animals. I grew up with pets my whole life, at some point I had 8 do… (more)

from
$45
per night
Confirmed availability: Memorial day
19.
Liz 
Verified Background Check
Lifelong animal lover!Winchester, MA, 01880
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Liz is an extremely conscientious, responsible and reliable dog sitter. She adapts her support for each dog differently depending on their needs and communicat… (more)

from
$50
per night
Confirmed availability: Memorial day
20.
Experienced & Energetic SitterMedford, MA, 02155
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

It is rare that you find someone so passionate about animals who is also incredibly responsible and mature! Lauren took wonderful care of my sister’s 7 year old… (more)

from
$60
per night

Rover also offers House Sitting in:

Rover.com is the simple, savvy way to find and book house sitting. It's easy to find the perfect house sitter - many sitters on Rover have a long history of house and 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. Every pet sitter on Rover has the option to complete a free background check, so look for their badge that says they've had the check done. Pet and house 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 house sitter on Rover. When you book with one of our trusted house sitters on Rover you get peace of mind that your home and pets are in loving hands.