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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What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Bonnie K.
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Sitter Profile Image: Bonnie K.
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1. Bonnie K.

Rover 101
Star Sitter
Your pet is my pet when with me.
Arlington, MA, 02474
2.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
104 reviews
44 repeat clients
from
$25
per visit
Profile image

Bonnie took great care of our 3yo lab/hound rescue dog. He has only been with us for three months and it was our first time away from him, so it was great to know he was in such good hands. She fed, walked and played with him--he got plenty of exercise and stimulation, and most importantly, attention!! With the snowstorm she ended up boarding him for one night at her house and he was well taken care of at her place. She even taught him to roll over! We will definitely hire Bonnie again.

Sitter Profile Image: Kelly M.
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Sitter Profile Image: Kelly M.
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2. Kelly M.

Star Sitter
Walking good in the neighborhood
Stoneham, MA, 02180
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
12 repeat clients
from
$17
per visit
Profile image

Kelly is a reliable and attentive caregiver and kept us informed with each morning and evening daily visit. Our cats warmed up to her in short time and we are so grateful for her care. We would be very happy to have her take care of our beloved kitties in the future. Thank you Kelly, for taking such great care of our boys!

Sitter Profile Image: Erin F.
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Sitter Profile Image: Erin F.
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3. 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
71 reviews
35 repeat clients
from
$20
per visit
Profile image

Erin did an exceptional job caring for our active and anxious dog Polly. We returned from a few days of vacation to find a happy, well fed and relaxed puppy. Erin carefully followed our care instructions and was very easy to work with. We would recommend Erin highly to care for any pet. Paul and Barbara

Sitter Profile Image: Claire H.
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Sitter Profile Image: Claire H.
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4. Claire H.

Star Sitter
Dogs are my best friends fur-ever!
Arlington, MA, 02474
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
10 repeat clients
from
$23
per visit
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Claire was kind, communicative (I got pics every day!), and really looked out for my cats while I was away on holiday - would 10/10 recommend!

Sitter Profile Image: Elisangela L.
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Sitter Profile Image: Elisangela L.
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5. Elisangela L.

Star Sitter
LOVE Paws,Claws,Fins,Feathers&More!
Woburn, MA, 01801
2.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
13 repeat clients
from
$20
per visit
Profile image

Elisangela and her girls were amazing! She took great care of our sweet cat Rudy when we were away for a long weekend. She was highly communicative throughout the entire process and left us feeling totally at ease that our guy was in great hands. We would recommend her and rebook with absolutely no hesitation!

Sitter Profile Image: Santhie J.
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Sitter Profile Image: Santhie J.
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6. Santhie J.

Star Sitter
Experienced dog walker & sitter
Melrose, MA, 02176
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
6 repeat clients
from
$20
per visit
Profile image

Santhie took excellent care of our dogs while we were away for the day, communicated when needed, and sent pictures to show the dogs were being taken care of.

Sitter Profile Image: Jacob Z.
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Sitter Profile Image: Jacob Z.
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7. Jacob Z.

Star Sitter
The dog whisperer.
Winchester, MA, 01890
0.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
52 reviews
17 repeat clients
from
$25
per visit
Profile image

Jacob did a wonderful job looking after our three cats while were out of town for a long weekend. I appreciated his thorough updates on how the girls were doing, a well as his attention to detail in taking care of them. He took the time to understand each of their routines and was thoughtful and attentive! He went above and beyond in spending time with them, as well as tidying up around their litter boxes. We'd definitely recommend Jacob for your cat sitting needs and look forward to booking with him in the future!

Sitter Profile Image: Cuan F.
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Sitter Profile Image: Cuan F.
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8. Cuan F.

Star Sitter
Animal Lover & Experienced Carer
Malden, MA, 02148
3.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$20
per visit

Cuan has had a love for animals and particularly dogs since he was an infant. We had a German Shepherd and a Rhodesian Ridgeback when Cuan was born. He was enchanted with them and they adored him. He took his first steps at the side of our German Shepherd “Wolf” . Cuan has always been very gentle and loving towards animals. Over the years he has spent time caring for and walking many dogs of different breeds from big to small. He has trained and cared for our two Jack Russell Terriers and looked after our friends Dachshunds. About 2 years ago Cuan adopted a stray Jack Russell Terrier “Stevie” and they have become inseparable. The bond between Stevie and Cuan is very apparent and they adore one another. Cuan is kind and compassionate and I would have no hesitation in recommending him as a dog walker or animal carer.

Sitter Profile Image: Sebastian O.
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Sitter Profile Image: Sebastian O.
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9. Sebastian O.

Reliable, loving and fun
Woburn, MA, 01801
1.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$15
per visit

Sebastian is my nephew. He has watched my dog Pepa on/off for the last 2 years as I have been traveling more often. Pepa absolutely loves him and Sebastian even managed to help Pepa shed some weight the vet recommended just by being more active with taking her on walks.

Sitter Profile Image: gianna f.
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Sitter Profile Image: gianna f.
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10. gianna f.

Lots of love to share with your pet
Stoneham, MA, 02180
2.8 mi. away
Drop-In Visits, Dog Walking
3 reviews
from
$19
per visit

Gianna is such a trusting pet sitter. She watched my Boxer while I was away overnight for a wedding and sent us frequent updates as request. Highly recommend.

Sitter Profile Image: Maria J.
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Sitter Profile Image: Maria J.
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11. Maria J.

Friendly neighborhood dog lover!
Medford, MA, 02155
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
1 repeat client
from
$10
per visit

About: I have grown up with dogs all my life, from large Pitts and Rottweilers to Jack Russel Terriers and chihuahuas. I love them all. I am also okay with dogs with some behavioral issues. My current family dog, Milo, has some leash aggression and we have been able to work through it the past 4 years we have had him. I am a fast learner and can follow directions very well. I would love to get to know your furry friend and help you out along the way! I get summer Fridays off from work so it leaves me with plenty of time to be able to house sit on weekend, or even do quick potty break, or walk throughout the day. I also get one work from home day a week (typically Mondays) that gives me additional flexibility. I am a true dog lover an will care for your pet(s) as if it were my own. I understand how important and loved your dog is along with your home. I will be very respectful of both and follow any instructions you give me.

Sitter Profile Image: Kimm & Kenn S.
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Sitter Profile Image: Kimm & Kenn S.
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12. Kimm & Kenn S.

Star Sitter
Love dogs, love to walk!
Woburn, MA, 01801
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
176 reviews
97 repeat clients
from
$30
per visit
Profile image

Kimm and Kenn are the very best cat sitters for us! They are (of course) reliable and leave personable notes, showing they care and make us feel better about leaving home, knowing our cat is in the best hands possible.

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
61 reviews
31 repeat clients
from
$25
per visit
Profile image

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

Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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14. Michael D.

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
26 reviews
12 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!

Sitter Profile Image: Sophia R.
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Sitter Profile Image: Sophia R.
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15. Sophia R.

I’ve had 5 pet dogs!
Medford, MA, 01890
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
51 reviews
10 repeat clients
from
$20
per visit
Profile image

Sophia was wonderful with our pup! She was communicative with me and made sure Chaco had extra water on a hot day! I will call on her assistance again for sure!

Sitter Profile Image: Tora C.
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Sitter Profile Image: Tora C.
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16. Tora C.

Lover of all animals!
Medford, MA, 02155
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
1 review
from
$17
per visit

Tora is a true animal lover! She has a wonderful soft heart for furry four legged friends. Now she is monitoring a Mommy bird with 4 eggs. She truly cares about the wellbeing and happiness of animals. They are almost like children to her. She would be a great asset to anyone who needs a pet walker or caregiver. She is responsible and attentive.

Sitter Profile Image: Nick L.
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Sitter Profile Image: Nick L.
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17. 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
12 reviews
1 repeat client
from
$17
per visit
Profile image

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.

Sitter Profile Image: Katherine P.
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Sitter Profile Image: Katherine P.
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18. Katherine P.

I love all dogs! Including yours!
Winchester, MA, 01890
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
2 repeat clients
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!

Sitter Profile Image: Emma I.
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Sitter Profile Image: Emma I.
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19. Emma I.

I'd love to help care for your pets
Winchester, MA, 01890
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$18
per visit

Emma cared for my shiba inu this past winter break for 2 weeks while I was traveling. They understood my instructions very clearly and were very communicative with me when I was gone. Shiba inus can sometimes be a little temperamental, but Emma handled him like a champ! I think they formed a great bond, and my little boy earned a new friend!

Sitter Profile Image: Dan Z.
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Sitter Profile Image: Dan Z.
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20. Dan Z.

Recent college grad dog-lover
Winchester, MA, 01890
0.3 mi. away
Drop-In Visits, Dog Walking
4 reviews
from
$20
per visit

quick and easy booking process, he came by and fed our dog and then went on a long walk. my bulldog was in a great mood when I came home

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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