Pet Sitting in Winchester

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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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Sitter Profile Image: Jessica and Dave S.
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Sitter Profile Image: Jessica and Dave S.
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1. Jessica and Dave S.

Star Sitter
5 star kitty care + dog walks
Arlington, MA, 02476
3.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
215 reviews
103 repeat clients
from
$24
per visit

We always get the cutest pictures of Selina hanging out with Dave. She really appreciates the company when we're gone, and we appreciate the peace of mind knowing she's well looked after.

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Sitter Profile Image: Erin F.
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Sitter Profile Image: Erin F.
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2. Erin F.

Star Sitter
Enthusiastic, flexible pet lover 😊
Woburn, MA, 01801
2.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
64 reviews
31 repeat clients
from
$20
per visit

Erin took great care of our kitty! She was communicative and responsive. With our car she was patient and understanding. Would recommend her!

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Sitter Profile Image: Cheryl R.
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Sitter Profile Image: Cheryl R.
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3. Cheryl R.

Star Sitter
Experienced and compassionate.
Woburn, MA, 01801
2.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
304 reviews
83 repeat clients
from
$20
per visit

Cheryl took amazing care of our cat Rogue and really went above and beyond in her care. We would recommend her to absolutely everyone and will definitely be reaching out to her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Chloe P.
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Sitter Profile Image: Chloe P.
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4. Chloe P.

Experienced dog walker and sitter!!
Burlington, MA, 01803
3.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
3 repeat clients
from
$17
per visit

Chloe is amazing, she is so sweet and caring to my fur babies! I highly recommend her and my pups love her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Cuan F.
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Sitter Profile Image: Cuan F.
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5. Cuan F.

Animal Lover & Experienced Carer
Malden, MA, 02148
3.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$18
per visit

Even as a young teen, I entrusted my dogs with Cuan. I have witnessed in him a complete air of warmth towards dogs. He is patient and appears to be able to take the perspective of the dog, thinking of what they would need, and being considerate of that. i wish he still lived nearer to us so that I could ask him to dog sit for us when needed. I wouldn't hesitate to recommend Cuan!

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Sitter Profile Image: Leah M.
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Sitter Profile Image: Leah M.
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6. Leah M.

Experienced pet professional.
Medford, MA, 02145
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
76 reviews
30 repeat clients
from
$25
per visit

Leah took amazing care of our cat while we were away for two weeks! Tosci warmed up to Leah super quickly and we would definitely trust Leah to take care of Tosci again the next time we go away 🙂

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Sitter Profile Image: Olivia S.
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Sitter Profile Image: Olivia S.
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7. Olivia S.

Rover 101
Star Sitter
Proactive, thoughtful caretaker!
Somerville, MA, 02144
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
4 repeat clients
from
$20
per visit

Olivia did a great job caring for my cat while I was on vacation! She played with her and gave her the attention she needed, and also kept a close eye on her eating habits to make sure everything was going okay. She gave clear updates that left me confident that my cat was doing well while I was gone. I'd definitely recommend Olivia and would ask her to cat-sit again!

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Sitter Profile Image: Stephanie H.
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Sitter Profile Image: Stephanie H.
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8. Stephanie H.

Friend to all pets- big and small
Burlington, MA, 01803
4.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$22
per visit

Took excellent care of my cat while I was away. My typically anxious cat felt completely comfortable around her. Stephanie kept me updated with photos and messages the entire time - she was very pleasant to interact with and very responsible!

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Sitter Profile Image: Daniel H.
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Sitter Profile Image: Daniel H.
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9. Daniel H.

I love dogs!!!
Somerville, MA, 02144
3.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$20
per visit

About: I have grown up with dogs around me since I was a baby. I have experience with caring for my own dogs as well as dogs of family/friends. I am currently a college student and would love to care for pets in my free time. I live in Singapore and I miss having a pet by my side so I would love to take care of your pets! I am free on most days during the week, just not during Monday and Wednesday from 2-5pm and Tuesday before noon due to my classes at Tufts. I am very active and am confident that I can take good care of your beloved fur babies! I am very responsive and will be easily contactable via phone.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lexi K.
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Sitter Profile Image: Lexi K.
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10. Lexi K.

Transgender Cat & Dog best friend
Somerville, MA, 02144
3.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$12
per visit

Lexi did a wonderful job taking care of our two cats. She was very responsive and communicative and sent us some cute pictures. She made sure they were fed, entertained, and cleaned the litter boxes. I also appreciated that she offered to take out trash, bring in the mail, and water plants. I will definitely use her services again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elisangela L.
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Sitter Profile Image: Elisangela L.
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11. Elisangela L.

LOVE Paws,Claws,Fins,Feathers&More!
Woburn, MA, 01801
2.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
11 repeat clients
from
$15
per visit

Elisangela was great with watching my two cats while I was away on vacation. She dropped in on the dates and times as discussed, sent plenty of updates and pictures. Would highly recommend!

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Sitter Profile Image: Anna L.
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Sitter Profile Image: Anna L.
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12. Anna L.

Star Sitter
Responsible dog lover
Arlington, MA, 02474
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
35 reviews
15 repeat clients
from
$20
per visit

Anna was fantastic! She visited my home to take care of my two cats while I was out of town. Anna was punctual and always provided an update with cute pictures of my fur babies after her visit. This was my second time booking Anna and I would definitely book her again!

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Sitter Profile Image: Erin L.
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Sitter Profile Image: Erin L.
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13. Erin L.

Rover 101
Star Sitter
Fitness goals! Pet More dogs!
Woburn, MA, 01801
2.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
60 reviews
30 repeat clients
from
$25
per visit

Thank you do much for a accommodating my last minute request! Erin was super responsive when arranging the drop in and texted through the visit

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Sitter Profile Image: Charlotte O.
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Sitter Profile Image: Charlotte O.
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14. Charlotte O.

Nurse who loves dogs!
Woburn, MA, 01801
2.5 mi. away
Drop-In Visits, Dog Walking
1 review
from
$18
per visit

Charlotte is an absolute lifesaver when it comes to dog walking! Her dedication, reliability, and genuine love for animals shine through in every interaction. My furry friend adores her daily walks with Charlotte, and I couldn't be happier knowing my pet is in such caring hands. I wholeheartedly recommend Charlotte for anyone in need of a trustworthy and compassionate dog walker.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Eunae L.
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Sitter Profile Image: Eunae L.
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15. Eunae L.

Star Sitter
Loving, Reliable & Gentle Auntie
Arlington, MA, 02476
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
57 reviews
24 repeat clients
from
$21
per visit

Eunae was great with our cat! Her service was seamless and impeccable! We could tell that our kitty had so much fun with her. I recommend her to everyone in the area. I will certainly book visits with her soon.

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Sitter Profile Image: Nick L.
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Sitter Profile Image: Nick L.
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16. Nick L.

Patient Pet Partner
Winchester, MA, 01890
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
1 repeat client
from
$17
per visit

Nick did a great job and he is very gentle and even our shy cat came did not hide or came out during just his second visit.

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Sitter Profile Image: Jacob Z.
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Sitter Profile Image: Jacob Z.
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17. Jacob Z.

The dog whisperer.
Winchester, MA, 01890
0.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
37 reviews
9 repeat clients
from
$20
per visit

Nucky loved doing zoomies with Jacob! Thank you!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Allie W.
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Sitter Profile Image: Allie W.
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18. Allie W.

Let me strut with your mutt
Medford, MA, 02155
2.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
49 reviews
18 repeat clients
from
$17
per visit

Allie was super great with our kitties!!! She was very responsive and went a nice little update each day with photos. Definitely would book again!! 😸

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Sitter Profile Image: Katherine P.
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Sitter Profile Image: Katherine P.
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19. Katherine P.

I love all dogs! Including yours!
Winchester, MA, 01890
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
40 years of experience
from
$17
per visit

About: I am a lifelong dog owner. I’ve owned large breed dogs my entire life (Dobermans). Also comfortable with small “passionate” dogs. Few things phase me, and I’m eager to support your needs. I’m also great with cats. I currently work from home, so love to break up my day with walks! Walking in most weather doesn't bother me, as long as it doesn't bother your dog! I am used to large and small dogs. Whether your dog is stubborn or easy going, nothing really phases me! I have a great read on animal behavior because I've been around animals of all kinds my entire life. We can walk or we can hang out in the yard and play. I am happy to do whatever your dog needs! I like to snap photos and take a video so you know how the visit goes!

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Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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20. Michael D.

Star Sitter
A loving experience for your pet!
Winchester, MA, 01890
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
24 reviews
11 repeat clients
from
$25
per visit

About: I grew up caring for dogs of various sizes and breeds. My children and I cherish the love and joy of having a pet to care for and play with. I no longer own a dog of my own, however we still want a furry friend to share our lives with. I'm an elementary teacher by day, however have afternoons, evenings, weekends, school vacations, and summers available to care for your dog. I am not home during most school days, however will not host a dog unless I am also scheduled to be home. There is a lot of space for one or two dogs to play inside our home. When caring for dogs, I will take them for walks in the park across the street or through one of the many walking paths in this area. It's our pleasure to play with your dog; keeping them engaged makes for a fun experience and helps keep their minds off of missing you!

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Winchester Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Winchester are rated on average 5 out of 5 stars based on 35 reviews.

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Winchester:

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.

Drop-In Visits