Dog Walking in Winchester

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Sitter Profile Image: Alina M.
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Sitter Profile Image: Alina M.
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1. Alina M.

Star Sitter
I will take care of your pet! 🐶🐱
Burlington, MA, 01803
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$22
per walk
5 out of 5.0 stars
38 reviews
13 repeat clients
Profile image

Alina has been fantastic with our little boy, Linus! She walks him four times a week, always sends wonderful pictures, and is incredibly caring and attentive. I highly recommend her as a dog walker and sitter!

Availability updated yesterday
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Leslie Y.
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Sitter Profile Image: Leslie Y.
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2. Leslie Y.

Star Sitter
Depending + Responsible dog walker
Lexington, MA, 02420
3.8 mi. away
Dog Walking
from
$20
per walk
5 out of 5.0 stars
16 reviews
5 repeat clients
Profile image

Leslie is very nice - it is easy to communicate with him, he is very accommodating to our rambunctious dog, and he is always on time! It is a pleasure to have him walking our dog, Archie :)

Availability updated 25 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: James T.
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Sitter Profile Image: James T.
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3. James T.

Let me be your pet’s spare human :)
Medford, MA, 02155
4.4 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
2 reviews
3 repeat clients
Profile image

Potato seems to love james! He’s always on time and takes the cutest pictures on their walks. Highly recommend

Availability updated 10 days ago
Sitter Profile Image: Shawn V.
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Sitter Profile Image: Shawn V.
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4. Shawn V.

Star Sitter
Keeping pets healthy, happy and ❤️
Arlington, MA, 02474
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per walk
5 out of 5.0 stars
71 reviews
19 repeat clients
Profile image

Wow, Shawn is AMAZING! Great with our pups. Prompt and very professional communication. Can’t say enough great things about her. Will absolutely work with her again!

Availability updated yesterday
Sitter Profile Image: Melinda C.
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Sitter Profile Image: Melinda C.
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5. Melinda C.

Kind and attentive care
Burlington, MA, 01803
3.6 mi. away
Drop-In Visits, Dog Walking
from
$17
per walk
5 out of 5.0 stars
14 reviews
5 repeat clients
Profile image

Melinda was great with my mother’s dog, Sophie! Sophie loved her too! I would recommend Melinda to anyone!

Availability updated 10 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Selena O.
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Sitter Profile Image: Selena O.
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6. Selena O.

Walks, Care, and Fun for your dogs!
Winchester, MA, 01890
0.6 mi. away
Dog Walking
from
$20
per walk
5 out of 5.0 stars
10 reviews
6 repeat clients
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Selena is a great walker for our pup! She is very communicative and does a great job taking care of Bailey. We would always recommend her to anyone in need of care!

Availability updated 14 days ago
Sitter Profile Image: Blane H.
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Sitter Profile Image: Blane H.
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7. Blane H.

Rover 101
Compassionate & Reliable Care
Medford, MA, 02155
2.7 mi. away
Drop-In Visits, Dog Walking
from
$17
per walk
5 out of 5.0 stars
5 reviews
2 repeat clients
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Blane was super nice and very patient with my shy little dog. He was professional and easy to work with. I would definitely recommend him!

Availability updated 2 days ago
Sitter Profile Image: shuyi g.
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Sitter Profile Image: shuyi g.
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8. shuyi g.

Expert Care & Attention!
Arlington, MA, 02476
3.3 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
2 reviews
1 repeat client
Profile image

Shuyi has treated Merlot with such great respect and kindness! I’ve seen my pup Merlot so happy and excited to see her on days when she helps me. I highly recommend her for any dog service! Thanks so much Shuyi!!

Availability updated 3 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Shannon C.
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Sitter Profile Image: Shannon C.
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9. Shannon C.

Dog lover since 05
Medford, MA, 02155
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
9 reviews

Shannon would be an amazing pet caregiver. She's grown up around animals and has extensive knowledge and intuition that come very naturally. She can quickly adapt to each pet's needs and provide them with the care and attention they require. She's responsible, compassionate, and would go above and beyond to ensure that you're pet is happy, healthy, and loved.

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Victoria D.
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Sitter Profile Image: Victoria D.
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10. Victoria D.

Loving pet sitter, works from home!
Arlington, MA, 02474
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$21
per walk
5 out of 5.0 stars
79 reviews
22 repeat clients
Profile image

Victoria was great, she was easy to communicate with and very accommodating for my bernese, she came right to where we were staying for a meet and greet to keep her calm.

Availability updated today
Sitter Profile Image: Matthew C.
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Sitter Profile Image: Matthew C.
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11. Matthew C.

Dogs and cats both welcome!
Arlington, MA, 02476
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
3 reviews

Matt walked my then-one-year-old pitt-mix Brody for a full semester in addition to his classes at Tufts. Matt was fantastic in every respect, always on time, always highly conscientious, and most importantly, always terrific with Brody. Brody loved his walks with Max, and I hope he can do more of them in the future!

Availability updated 3 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Natalie J.
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Sitter Profile Image: Natalie J.
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12. Natalie J.

Star Sitter
Here to keep the happy tails waggin
Medford, MA, 02155
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per walk
5 out of 5.0 stars
88 reviews
31 repeat clients
Profile image

Natalie always takes great care of my pup! She was especially helpful today when I reached out last minute and she was still available for a dog walk! Thank you!!

Availability updated today
Sitter Profile Image: Ken G.
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Sitter Profile Image: Ken G.
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13. Ken G.

Canine volunteer & digital nomad
Arlington, MA, 02476
2.7 mi. away
Drop-In Visits, Dog Walking
from
$19
per walk
5 out of 5.0 stars
11 reviews
1 repeat client
Profile image

Ken was my savior today. I have been feeling sick all day and Ken accepted a walk last minute so my antsy dog could get much needed outdoor time. Thank you

Availability updated 4 days ago
Sitter Profile Image: Lourdes S.
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Sitter Profile Image: Lourdes S.
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14. Lourdes S.

Star Sitter
I prefer dogs to Humans! 🫶🐶
Arlington, MA, 02476
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
16 reviews
7 repeat clients
Profile image

Lindy is amazing! There were some issues getting into my house and she was very flexible about dealing with the frustration. She’s great with my dog, who is very high energy and can sometimes be overwhelming to people. So awesome!!!

Availability updated 24 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Caitlin M.
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Sitter Profile Image: Caitlin M.
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15. Caitlin M.

Rover 101
Star Sitter
Cat Whisperer and Canine Companion
Medford, MA, 02155
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per walk
5 out of 5.0 stars
334 reviews
110 repeat clients
Profile image

Caitlin is superb (and then some!)! Delilah loves seeing her for walks, and Caitlin is incredibly attentive. She learns her cues, and understands Delilah’s needs like no one else. Could not recommend more!

Availability updated yesterday
Sitter Profile Image: Julia Alves L.
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Sitter Profile Image: Julia Alves L.
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16. Julia Alves L.

Affection and care for your pet!
Woburn, MA, 01801
1.7 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
4 reviews
1 repeat client

Julia demonstrated excellent work with my pets. She is truly dedicated and concerned about the well-being of the animals. I always trust her to care for my pets and have no doubt that she is highly qualified for this. In addition to growing up with animals of various sizes, she has years of experience as a dog and cat caregiver. I highly recommend her work!

Availability updated 75 days ago
Sitter Profile Image: Margaret F.
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Sitter Profile Image: Margaret F.
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17. Margaret F.

Dog lover + Zoo Keeper Volunteer!
Winchester, MA, 01890
0.9 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
2 reviews

I have had the pleasure of knowing Margaret for many years. I can say with confidence her care, compassion, dedication and love for animals is truly remarkable. Margaret has an attention for detail and commitment to each pet's unique needs. She's dependable and always ensures your pets feel safe and loved. I wholeheartedly recommend Margaret as an animal sitter to anyone looking for someone trustworthy, attentive, and truly passionate about animal well-being. Sheryl, Sofie and Louie

Availability updated 4 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: marilyn g.
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Sitter Profile Image: marilyn g.
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18. marilyn g.

Animal Welfare Specialist
WINCHESTER, MA, 01890
0.3 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$25
per walk
2 reviews

Hi, I am a dog and cat Mom, I have had Marilyn watch all my pets for many years. What I think sets Marilyn apart from other sitters I have had is her experience as a veterinary technician. She has been such a huge help with some of my medically complicated or geriatric pets over the years! She goes the extra mile to make sure they get the care they need. I’m so thankful we have her!

Availability updated 4 days ago
Sitter Profile Image: Kelly D.
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Sitter Profile Image: Kelly D.
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19. Kelly D.

Knowledgeable, Observant & Caring
Woburn, MA, 01801
1.1 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$23
per walk
5 out of 5.0 stars
8 reviews
4 repeat clients
Profile image

I was impressed that the first walk without prior introduction went smoothly. Chip seemed relaxed and happy. Kelly sent me pictures too, which was reassuring

Availability updated 35 days ago
Sitter Profile Image: March A.
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Sitter Profile Image: March A.
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20. March A.

Caring and responsible animal lover
Medford, MA, 02155
1.4 mi. away
Boarding, Dog Walking
from
$25
per walk
5 out of 5.0 stars
3 reviews
1 repeat client

My family spend significant time with March and his delightful dog, Obi-Wan. I could see what a devoted, caring, responsible pet owner March was by Obi-Wan's absolute devotion to him - the dog wanted to follow March everywhere, and greeted him excitedly whenever he arrived home. March's large house and yard were very well suited for a dog. Obi-Wan had lots of energy, which March managed well with regular walks and exercise in the woods next to his house. This care and training really showed in Obi-Wan's mood and behaviour, which were excellent. Obi-Wan was always very gentle and affectionate with everyone, including excitable children - he genuinely seemed to enjoy the very frequent cuddles my 3-year-old demanded of him! I would not hesitate to put any pet of mine in March's care: March was a caring, responsible, unflappable pet owner.

Availability updated 8 days ago

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