Pet Sitting in Winthrop

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Sitter Profile Image: David M.
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Sitter Profile Image: David M.
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1. David M.

Star Sitter
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
118 reviews
46 repeat clients
from
$24
per visit
Profile image

David has been awesome with Roxi! He is great at communicating if he's running late, when he is grouping her together with other dogs, and clarifying if something looks odd in the schedule. He has been really accommodating with last minute changes, and making sure he prioritizes her safety.

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Sitter Profile Image: Tyler H.
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Sitter Profile Image: Tyler H.
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2. Tyler H.

Star Sitter
Experienced puppy dad
Chelsea, MA, 02150
3.1 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
35 reviews
12 repeat clients
from
$21
per visit
Profile image

Tyler is the absolute best! I work full time and Tyler’s drop ins definitely help the day go faster for Bea. She does zooms around Tyler which she only does with people she’s comfortable with. Tyler is very communicative and friendly, and it’s nice to be able to trust someone to watch Bea. She can be high energy and I can tell that Tyler is patient with her. I definitely would recommend Tyler!

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Alexandra L.
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Sitter Profile Image: Alexandra L.
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3. Alexandra L.

Star Sitter
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
35 reviews
11 repeat clients
from
$25
per visit
Profile image

Best. Catsitter. Ever!! Alexandra did a exceptional job looking after my two kitties while I was visiting family for the holidays. This was my first time leaving them behind so I was nervous, but I was quickly put at ease by Alexandra’s adorable pictures and hilarious recaps of the visits. The kitties warmed right up to her, probably because she was so generous with the playtime, treats, and love. She is dependable and reliable — she always showed up on time, stayed for the duration of the visit, and sent me plenty of updates. I came back to a tidy home and two happy cats. If you’re an anxious cat mom like me, Alexandra is the catsitter for you! 10/10!! ❤️

Sitter Profile Image: Elliott M.
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Sitter Profile Image: Elliott M.
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4. Elliott M.

Star Sitter
Enthusiastic dog owner/walker
Boston, MA, 02118
3.0 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
85 reviews
57 repeat clients
from
$16
per visit
Profile image

Great experience so far. Timely and flexible. Understanding when our pupp went to the hospital and we had to cancel on short notice.

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Bridget M.
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Sitter Profile Image: Bridget M.
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5. Bridget M.

Star Sitter
Excited to meet your pets !
Winthrop, MA, 02152
1.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
7 repeat clients
from
$20
per visit
Profile image

Bridget is wonderful! Caring and kind, understood my Jerry (cat) well. Went out of her way to make sure he was loved! Highly recommend. ⭐️⭐️⭐️⭐️⭐️

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Tawana H.
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Sitter Profile Image: Tawana H.
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6. Tawana H.

Star Sitter
Fun, loving and trusted sitter!
Revere, MA, 02151
3.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
45 reviews
33 repeat clients
from
$28
per visit
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Tawana was on time and brought Udon her smaller dog which was excellent! They played great and my puppy really needs the socialization. excellent drop in.

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Jennifer R.
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Sitter Profile Image: Jennifer R.
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7. Jennifer R.

understanding and patient
Winthrop, MA, 02152
0.4 mi. away
Drop-In Visits, Dog Walking
1 review
1 repeat client
from
$15
per visit

Jennifer is one of the best dog walkers I have ever worked with. She is consistently on time and cares deeply for the dogs she walks. She is incredibly patient, even with reactive dogs. If you want your dogs to be cared for and adored on their walks with someone who is reliable, safe, and has had years working with dogs, then Jennifer is your girl!

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Katie & Dave M.
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Sitter Profile Image: Katie & Dave M.
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8. Katie & Dave M.

Grad students who love pups!
East Boston, Boston, MA, 02128
2.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
15 reviews
4 repeat clients
from
$20
per visit

Katie & David took great care of my dog Penny for a few days while away on a work trip. They are caring, responsible and responsive. And, I could count on them to make sure she got her daily medication and was well taken care of while I was away!

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Sitter Profile Image: Kayla G.
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Sitter Profile Image: Kayla G.
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9. Kayla G.

Star Sitter
Stay at home dog mom!
Revere, MA, 02151
2.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
50 reviews
18 repeat clients
from
$25
per visit
Profile image

Kayla is kind, fantastic and took great care of my large dog during drop in visits while I was away. I received plenty of pictures and updates about walks/food and how he was doing. Highly recommend!

Confirmed availability: 4th of July Weekend
Sitter Profile Image: river t.
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Sitter Profile Image: river t.
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10. river t.

Star Sitter
dog walker, dog sitter, dog lover!!
East Boston, east boston, MA, 02128
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
44 reviews
19 repeat clients
from
$25
per visit

River is a great candidate for taking care of pets! She has showed nothing but love for mine and she is great at interacting with them. She is very dependable and will always be there for you.

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Lara B.
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Sitter Profile Image: Lara B.
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11. Lara B.

College Student looking for work!
East Boston, Boston, MA, 02128
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$15
per visit

Lara took care of my cat for 3 years while in high school. She is a responsible, efficient and loving caretaker who is great at taking care of animals!

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Ryan H.
Sitter Profile Image: Ryan H.

12. Ryan H.

Star Sitter
A new best bud for your fur babies
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
$30
per visit
Profile image

Ryan is professional and knowledgeable about dogs. He is always prompt and communicative. My pup Henry is a rescue who is learning manners. Ryan's patience and kindness have made his time with him exceptional.

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Sitter Profile Image: Kayla C.
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Sitter Profile Image: Kayla C.
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13. Kayla C.

Star Sitter
Stay at Home Dog Mom
East Boston, MA, 02128
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
59 reviews
23 repeat clients
from
$35
per visit
Profile image

Thank you so very much Kayla for your patience, excellent communication, and flexibility with this latest session with Atlas!! Words simply cannot fully describe my gratitude!

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Valeria G.
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Sitter Profile Image: Valeria G.
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14. Valeria G.

Tails Up! Pet Sitting Excellence
East Boston, Revere, MA, 02151
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
2 repeat clients
from
$25
per visit

I had the pleasure of having Valeria take care of my puppy, and I honestly couldn't have been happier with her service. Valeria's dedication and genuine love for pets really showed through in her pet sitting. She followed all instructions to the T, and built a very good relationship with my little girl. She went above and beyond to ensure my pet was comfortable, happy, and well-cared for. I highly recommend Valeria to anyone seeking a responsible and loving pet caregiver.

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Rob S.
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Sitter Profile Image: Rob S.
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15. Rob S.

S tier dog walker/sitter w 3 dogs
Winthrop, MA, 02152
0.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$21
per visit

Rob has been taking care of my Boston terrier for a couple of years now and he’s been a great and reliable dog sitter and walker. My dog gets so excited when he comes to pick her up to go for a walk or to spend the night. Rob is personable, trustworthy and great with animals. I am glad to have met him for my pup.

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Sitter Profile Image: Esthefany H.
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Sitter Profile Image: Esthefany H.
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16. Esthefany H.

Providing Dog Fulfillment & Fun
East Boston, East Boston, MA, 02128
1.1 mi. away
Boarding, Drop-In Visits, Dog Walking
2 reviews
1 repeat client
from
$30
per visit

Esthefany has known my dog since he was a puppy. She has always been very patient and caring with him. My dog is very active. However, Esthefany has always had the patience to train him and walk him. Often times when she sees him she brings him treats and dog products that she thinks he will need. She takes time to watch his behaviors and make sure he isn't anxious or overwhelmed when participating in activities with him. Esthefany adores my dog and makes sure to always show it.

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Sitter Profile Image: Adam F.
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Sitter Profile Image: Adam F.
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17. Adam F.

Friendly animal lover
Boston, MA, 02128
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$20
per visit
Profile image

Adam was great! Good communication and my cats were well taken care of.

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Kathryn A.
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Sitter Profile Image: Kathryn A.
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18. Kathryn A.

Rover 101
Star Sitter
Animal lover and friend to all.
Winthrop, MA, 02152
0.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
55 reviews
12 repeat clients
from
$30
per visit
Profile image

Our 14 month-old puppy had a great visit with Kat and her dog, Lily. She was easy to reach and provided photos and an update about the visit. We will happily use Kat's services again.

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Sitter Profile Image: Carol C.
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Sitter Profile Image: Carol C.
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19. Carol C.

Outgoing, loves animals!
Winthrop, MA, 02152
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
3 repeat clients
from
$14
per visit
Profile image

Carol checked on my cat twice a day while I was away for a week. She was wonderful! She gave him the attention he needed and kept me updated with pictures and details of his day. Carol is reliable and attentive!

Confirmed availability: 4th of July Weekend
Sitter Profile Image: Vanessa S.
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Sitter Profile Image: Vanessa S.
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20. Vanessa S.

Extra snuggles included!
Winthrop, MA, 02152
0.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$25
per visit
Profile image

Vanessa took wonderful care of my Sully. She provided a detailed care card at the end of each visit and included photos as well! Very attentive and responsive. I truly appreciated her help while I was away for the weekend, and Sully enjoyed her company even more! 10/10 sitter- will definitely book again! Thanks for all your help!!!

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Winthrop Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Winthrop are rated on average 5 out of 5 stars based on 66 reviews.

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Rover.com is the simple, savvy way to find and book drop in pet sitting. It's easy to find the perfect pet sitter - many sitters have worked through Rover for years 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. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet 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 pet sitter on Rover. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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