House Sitting in Winthrop

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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Sitter Profile Image: Deanna S.
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Sitter Profile Image: Deanna S.
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1. Deanna S.

Animal lover, remote worker
Malden, MA, 02148
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
3 repeat clients
from
$55
per night

Deanna took great care of our puppy, Walnut! She sent adorable updates so we knew our girl was safe and happy. Would definitely have Deanna look after Wally again!

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Sitter Profile Image: Andrew T.
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Sitter Profile Image: Andrew T.
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2. Andrew T.

Friendly, convenient sitter/walker
Medford, MA, 02155
6.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
57 reviews
21 repeat clients
from
$75
per night

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 were nervous about leaving our puppy with someone but Andrew put us at ease and he was great at sending updates. Can’t say enough good things about him!

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Sitter Profile Image: Iain M.
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Sitter Profile Image: Iain M.
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3. Iain M.

Radiate Peace Pet Care
CHELSEA, MA, 02150
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
7 repeat clients
from
$62
per night

Iain is the most thoughtful, perceptive, caring petsitter I have ever had. Iain watched my two cats for a week while I was away, and made me feel immediately at ease with photo and text updates. I am blown away by the care, attention, and love Iain gave to my cats while I was away. My older cat needs a lot of attention and tends to get stressed while I am away, but I can tell by the photos and updates that he was perfectly content. My younger cat is very shy, and I can tell Iain respected her boundaries and gained her trust. Iain also left my apartment absolutely spotless and followed every single instruction given! I’ve already re-booked Iain for my next trip out of town and highly recommend!

Confirmed availability: Easter Weekend
Sitter Profile Image: Kelly R.
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Sitter Profile Image: Kelly R.
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4. Kelly R.

I’ll walk your pup! Rain or shine!
Boston, MA, 02128
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 reviews
16 repeat clients
from
$65
per night

Kelly was amazing! She took great care of my dog and he had no anxiety when I got home, which is amazing. She stayed in my house which was so helpful and she even vacuumed which was so not necessary but extremely kind. Will definitely be booking with Kelly again in the future and I recommended her to a few friends locally!

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Sitter Profile Image: David M.
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Sitter Profile Image: David M.
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5. David M.

Dave's Doggy Day Care
North Dorchester, Dorchester, MA, 02125
5.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
62 reviews
31 repeat clients
from
$90
per night

I cannot recommend David enough. We book him for walks and dog sitting. He’s on time, professional, caring, kind and communicative. And our dogs love him!

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Sitter Profile Image: Kayla C.
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Sitter Profile Image: Kayla C.
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6. Kayla C.

Stay at Home Dog Mom
Boston, MA, 02128
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
45 reviews
21 repeat clients
from
$65
per night

Kayla was amazing with Olive for a full week in our home. It was great to have her there taking care of our high energy dog! We would have her back in a heartbeat!

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Sitter Profile Image: tatiana w.
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Sitter Profile Image: tatiana w.
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7. tatiana w.

pet lover
everett, MA, 02149
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$55
per night

Tatiana was great! Our puppy loved her! She sent so many fun photos and provided great updates throughout the whole stay! We would absolutely book her again!

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Sitter Profile Image: Paul R.
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Sitter Profile Image: Paul R.
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8. Paul R.

Flexible Availability, Former Owner
Boston, MA
4.0 mi. away
House Sitting
5.0 out of 5 stars
10 reviews
1 repeat client
from
$80
per night

Paul has been super professional every step of the way. He was prompt in setting up a meet and greet, on time, and communicated well. He also caught my mistake when I initially booked for the wrong days. We received some updates while we were gone, which was appreciated, but most importantly, our girl was clearly well taken care of. She's old and thrives on routine, and she looked like she barely noticed we were gone when we returned. It's really nice to know that she was in great hands. Bonus: I think our apartment was actually cleaner when we returned. 5+ stars.

Sitter Profile Image: Natalie H.
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Sitter Profile Image: Natalie H.
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9. Natalie H.

Pets are my Everything.
Revere, MA, 02151
1.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$50
per night

Natalie was wonderful. She gave us tons of updates and pictures, and was patient and caring with both of our dogs. One of our dogs is super shy around people he doesn't know, and she took the time to make him comfortable and even was able to get him to play with her, which is super rare for him! Our other dog needed medicine administered, and she was great about managing that and giving us appropriate updates. We can home to two happy pups. I would definitely recommend Natalie!

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Sitter Profile Image: Adam F.
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Sitter Profile Image: Adam F.
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10. Adam F.

Animal lover saving for wedding
Boston, MA, 02128
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$70
per night

Adam watched our Saint Bernard while we were away and he did such a great job leaving us updates. We were not worried about our dog at all while we were gone

Confirmed availability: Easter Weekend
Sitter Profile Image: river t.
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Sitter Profile Image: river t.
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11. river t.

dog walker, dog sitter, dog lover!!
East Boston, east boston, MA, 02128
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
37 reviews
16 repeat clients
from
$85
per night

River took care of my pup in our home for two nights. She organized a meet and greet before the booking and was quick to respond to messages. Throughout her stay, she provided lots of updates which I greatly appreciated and was able to accommodate a longer stay when our flight was cancelled. I worry about new sitters walking my three year old dog because she is reactive and very strong, but River was confident in handling her and that put me at ease. We returned to a happy and healthy dog and clean home! I would recommend River and would hire her again.

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Sitter Profile Image: Leslie O.
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Sitter Profile Image: Leslie O.
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12. Leslie O.

It’s about your pets happiness!
East Boston, Boston, MA, 02128
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$80
per night

Leslie was a great sitter for our dog Trudy. She sent lots of updates and took great care of her. We really appreciate that she could help us out on fairly late notice over a holiday weekend!

Confirmed availability: Easter Weekend
Sitter Profile Image: Alexandra L.
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Sitter Profile Image: Alexandra L.
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13. Alexandra L.

Happy to help your fur family🐾
Winthrop, MA, 02152
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
11 repeat clients
from
$115
per night

It's our second time having Alexandra house sit for us, and she took excellent care of our dog and cat! This time we even asked her to do some extra things, like apply a topical spray to our dog's stomach, and give him pills to treat an infection. Alexandra was amazing, sent updates and photos and took great care of the boys!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Avonlea B.
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Sitter Profile Image: Avonlea B.
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14. Avonlea B.

Bully Breed Buddy
Winthrop, MA, 02152
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$111
per night

It was such a pleasure leaving our pets in such good hands. Really great to not have to worry. Avonlea was so kind and attentive! Thank you a million!!!!

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Sitter Profile Image: Gabriel L.
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Sitter Profile Image: Gabriel L.
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15. Gabriel L.

Rover 101
Your pets next best friend!
Boston, MA, 02128
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
35 reviews
9 repeat clients
from
$70
per night

Gabriel did an awesome job with Frex. He sent plenty of pictures and updates, and he left my apartment in excellent condition at the end. I would definitely use Gabriel again!

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Sitter Profile Image: Theresa R.
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Sitter Profile Image: Theresa R.
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16. Theresa R.

Your dog is like our dog
East Boston, East Boston, MA, 02128
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
15 reviews
4 repeat clients
from
$65
per night

Theresa and Henry are wonderful caretakers! They were very attentive with our senior dog and followed the detailed instructions for food and medical care that we provided. Plus we got cute photos and updates daily! Highly recommended!

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Sitter Profile Image: Samantha S.
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Sitter Profile Image: Samantha S.
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17. Samantha S.

Samantha's Rover Retreat
East Boston, Boston, MA, 02128
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$31
per night

Was out of town for 3 months for work and Samantha took great care of my disabled cat Louis! She initially was coming to our house to cat sit and since it went so well I just allowed her to cat sit him at her home. He absolutely loved her and she still takes care of him for my vacations. Super nice girl, great communication and knowledgeable of care for pets with special needs.

Confirmed availability: Easter Weekend
Sitter Profile Image: Ryan H.
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Sitter Profile Image: Ryan H.
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18. Ryan H.

A new best bud for your furry kids
Winthrop, MA, 02152
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
5 repeat clients
from
$85
per night

Ryan was a perfect example of what a loving caregiver should be. He was professional, kind, and reliable. I trust Ryan and would hire him again. #highlyrecommended

Confirmed availability: Easter Weekend
Sitter Profile Image: Ana L.
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Sitter Profile Image: Ana L.
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19. Ana L.

Animal lover, world traveler
Winthrop, MA, 02152
0.4 mi. away
House Sitting
from
$75
per night

Ana was great with Mickey our 12 year old dog. Mickey can bark at people when he first meets them, but he liked Ana right away. She sent us numerous updates, photos and videos which were great to see as we were halfway around the world on vacation. The house was kept very clean and Mickey was well tended to. We would definitely invite Ana to dogsit again.

Sitter Profile Image: Nicolette M.
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Sitter Profile Image: Nicolette M.
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20. Nicolette M.

Homemade biscuits and a loving home
Winthrop, MA, 02152
0.7 mi. away
Boarding, House Sitting, Doggy Day Care
5.0 out of 5 stars
13 reviews
from
$75
per night

Nicolette has taken care of our dog, Lucy, multiple times when we go out of town for a long vacation. And every time, Lucy is treated like she is on vacation as well. Nicolette will treat your pet as if they were hers, returning fresh, relaxed, and well cared for! You will have peace of mind with Nicolette as your pet’s sitter!

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Winthrop House Sitting ratings

Overall Rating:
5.0 out of 5 stars

House sitters in Winthrop are rated on average 5 out of 5 stars based on 38 reviews.

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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.

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